Esters — Paper 1 · A Level Chemistry 9701

28 What is the structure of the ester formed from propanoic acid and ethanol? A B H H H O O H H H H H H C C H C C C O C C C H O C C H H H H H H H H H C D H H H O O H C H H H H C C H C C O C H O C C H H H H C H H H H

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2005

30 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium hydroxide? A CH3OH B C3H7OH C C3H7CO2H D C H CO −Na + 3 7 2

1 marks

Answer: B

This question in 9701/11 May/June 2006

28 A common industrial solvent is a mixture of propanone, CH3COCH3, and pentyl ethanoate CH3CO2(CH2)4CH3. Which reagent would have no effect on this solvent? A Na(s) B NaBH4 C NaOH(aq) D 2,4-dinitrophenylhydrazine reagent

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2006

30 Which pair of compounds is formed when the ester C2H5CO2CH3 is boiled with aqueous sodium hydroxide? A C2H5CO2H CH3OH B C2H5CO2Na CH3ONa C C2H5CO2Na CH3OH D C2H5OH CH3CO2Na

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2006

40 Rofecoxib, an efficient drug against arthritis, has the following structure. R is an inert group. R CH2 C O * C C O Which reactions are possible with this structure? 1 The bond marked is hydrolysed by heating with aqueous sodium hydroxide. 2 Aqueous bromine is decolourised. 3 An orange precipitate is formed with 2,4-dinitrophenylhydrazine reagent.

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2006

30 The ester CH3CH2CH2CO2CH3 is responsible for the aroma of apples. When this ester is hydrolysed by acid in the stomach, what is the empirical formula of the organic acid produced? A CH4O B C2H4O C C2H4O2 D C3H7O2

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2007

24 Mevalonic acid, 3,5-dihydroxy-3-methylpentanoic acid, is involved in cholesterol formation in the body. It is an oil that occurs as a mixture of the two interchanging molecules shown in the diagram. HO CH3 HO CH3 C C I CH2 CH2 CH2 CH2 II CH2 C CH2OH CO2H O O What names are used to describe the pair of interchanging reactions I and II? A condensation and addition B dehydrogenation and hydrogenation C esterification and hydrolysis D neutralisation and acidification

1 marks

Answer: C

This question in 9701/11 May/June 2008

30 Compound X, C6H12O, is oxidised by acidified sodium dichromate(VI) to compound Y. Compound Y reacts with ethanol in the presence of a little concentrated sulphuric acid to give liquid Z. What is the formula of Z? A CH3(CH2)2CH=CHCO2H B CH3(CH2)4CH2COCH2CH3 C CH3(CH2)4CO2CH2CH3 D CH3CH2CO2(CH2)4CH3

1 marks

Answer: C

This question in 9701/11 May/June 2008

37 Aspirin is a widely-available pain-killer, whose properties have been known for centuries. The structure of aspirin is shown. OH C O O C CH3 O Which functional groups are present in aspirin? 1 alcohol 2 carboxylic acid 3 ester

1 marks

Answer: C

This question in 9701/11 May/June 2008

39 The compound cholesterol has the following structure. CH3 CH2 CH2 CH3 CH CH2 CH CH3 CH3 CH3 CH2 CH CH CH2 C C CH2 CH C CH CH2 HO CH2 CH Which statements are correct? 1 Cholesterol reacts with a mixture of ethanoic acid and concentrated sulphuric acid. 2 Cholesterol reacts with bromine to form a compound which has two new chiral centres. 3 Cholesterol is oxidised by acidified sodium dichromate(VI) to form an aldehyde.

1 marks

Answer: B

This question in 9701/11 May/June 2008

26 Ethyl phenylethanoate, C6H5CH2CO2C2H5, gives a characteristic flowery aroma to honey. Which sequence of reagents, with heating in each case, leads to the preparation of C6H5CH2CO2C2H5 from C6H5CH2Br? NaOH(aq) C2H5COCl A C6H5CH2Br NaOH(aq) C2H5CO2H, conc. H2SO4 B C6H5CH2Br NaCN(alcoholic) H+(aq) C2H5OH, conc. H2SO4 C C6H5CH2Br NaOH(aq) conc. MnO4, H+(aq) – C2H5OH, conc. H2SO4 D C6H5CH2Br

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2008

28 Bees use 2-methylbutyl ethanoate as an ‘alarm’ pheromone. When disturbed, individual bees on guard will raise their abdomen and emit the alarm pheromone, fanning their wings to aid its dispersal. This alerts other bees to a danger and makes them ready to sting when required. H O H H H H H C C O C C C C H H H H H H C H H 2-methylbutyl ethanoate Which starting materials would be required to synthesise 2-methylbutyl ethanoate? A CH3CH2OH and CH3CH2CH(CH3)CO2H B CH3CO2H and CH3CH2CH(CH3)CH2OH C CH3CH2OH and CH3CH2CH(CH3)CH2CO2H D CH3CO2H and CH3CH2CH(CH3)CH2CO2H

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2008

30 Use of the Data Booklet is relevant to this question. Ethyl ethanoate can be obtained from ethanoic acid and ethanol by the following reaction. CH3CH2OH + CH3CO2H CH3CO2CH2CH3 + H2O Ethanol (30 g) and ethanoic acid (30 g) are heated under reflux together, and 22 g of ethyl ethanoate are obtained. What is the yield of the ester? A 25 % B 38 % C 50 % D 77 %

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2008

27 Which ester is formed when the alcohol CH3CH2OH is reacted with CH3CH2CH2CO2H? A ethyl propanoate B ethyl butanoate C propyl ethanoate D butyl ethanoate

1 marks

Answer: B

This question in 9701/11 May/June 2009

30 A compound Y has the following properties. • It is a liquid at room temperature and atmospheric pressure. • It does not mix completely with water. • It does not decolourise acidified potassium manganate(VII). What could Y be? A ethane B ethanoic acid C ethanol D ethyl ethanoate

1 marks

Answer: D

This question in 9701/11 May/June 2009

40 A sun protection cream contains the following ester as its active ingredient. CH2CH3 CH3O CH CHCO2CH2CH CH2CH2CH2CH3 What are the products of its partial or total hydrolysis by aqueous sodium hydroxide? 1 CH3CH2CH2CH2CH(CH2CH3)CH2OH 2 CH3O CH CHCO2 Na+ – 3 CH3O CO2 Na+ –

1 marks

Answer: B

This question in 9701/11 May/June 2009

30 The acarid mite releases Iardolure to attract other mites to a host. This chemical can be destroyed by hydrolysis with acid. CH3CH2CH2[CH(CH3)CH2]3CH(CH3)O C H O A simplified formula for lardolure may be written as follows. RCH(CH3)O C H O What are the products of its hydrolysis? A RCH(CH3)CO2H + CH3OH B RCH(CH3)CO2H + HCO2H C RCH(CH3)OH + CO2 D RCH(CH3)OH + HCO2H

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2009

25 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium hydroxide? A CH3OH B C3H7OH C C3H7CO2H D C H CO − N a + 3 7 2

1 marks

Answer: B

This question in 9701/11 May/June 2010

24 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium hydroxide? A CH3OH B C3H7OH C C3H7CO2H D C H CO − N a + 3 7 2

1 marks

Answer: B

This question in 9701/12 May/June 2010

25 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium hydroxide? A CH3OH B C3H7OH C C3H7CO2H D C H CO − N a + 3 7 2

1 marks

Answer: B

This question in 9701/13 May/June 2010

21 Compound X reacts with ethanoic acid in the presence of an H+ catalyst to produce the compound below. O H H O H3C C C C O C CH3 H H What is the molecular formula of compound X? A C2H6O2 B C2H6O3 C C4H8O D C4H8O2

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2010

24 Esters are frequently used as solvents and as flavouring agents in fruit drinks and confectionery. An ester C8H12Br2O4 can be prepared in low yield by the reaction shown. CH3C(Br)(CH2Br)CO2H + (CH3)2C(OH)CO2H ⇌ C8H12Br2O4 + H2O What is the structural formula of the ester C8H12Br2O4? A CH3C(Br)(CH2Br)CO2C(CH3)2CO2H B CH3C(Br)(CH2Br)CO2C(OH)(CH3)CO2CH3 C CH3C(Br)(CH3)CO2C(CH3)2CO2CH2Br D (CH3)2C(Br)C(CO2H)(CH2Br)CO2CH3

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2010

38 Organic acids and alcohols react together to form esters. Which pairs of compounds could produce a product of molecular formula C4H6O4? 1 CH3CO2H and C2H5OH 2 HCO2H and HOCH2CH2OH 3 HO2CCO2H and CH3OH

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2010

22 Compound X reacts with ethanoic acid in the presence of an H+ catalyst to produce the compound below. O H H O H3C C C C O C CH3 H H What is the molecular formula of compound X? A C2H6O2 B C2H6O3 C C4H8O D C4H8O2

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2010

27 Which formula represents an ester which will form sodium ethanoate on hydrolysis with aqueous sodium hydroxide? A B O O H3C CH2 C O CH2 CH3 H3C CH2 C O CH3 C D O O H C O CH2 CH3 H3C C O CH2 CH2 CH3

1 marks

Answer: D

This question in 9701/11 May/June 2011

28 The ester CH3CH2CH2CO2CH3 is responsible for the aroma of apples. When this ester is hydrolysed by acid in the stomach, what is the empirical formula of the organic acid produced? A CH2O B CH4O C C2H4O D C3H6O2

1 marks

Answer: C

This question in 9701/12 May/June 2011

21 Acrylic acid is produced from propene, a gaseous product of oil refineries. O x y OH acrylic acid Which statement about acrylic acid is not correct? A Both bond angles x and y are approximately 120°. B It decolourises aqueous bromine. C It gives an orange precipitate with 2,4-dinitrophenylhydrazine reagent. D It reacts with an alcohol to give an ester.

1 marks

Answer: C

This question in 9701/13 May/June 2011

28 Which formula represents an ester which will form sodium ethanoate on hydrolysis with aqueous sodium hydroxide? A B O O H3C CH2 C O CH2 CH3 H3C CH2 C O CH3 C D O O H C O CH2 CH3 H3C C O CH2 CH2 CH3

1 marks

Answer: D

This question in 9701/13 May/June 2011

30 Which pair of substances could react to give the ester CH3CH2CO2CH3? A ethanol and ethanoic acid B methanol and ethanoic acid C methanol and propanoic acid D propan-1-ol and methanoic acid

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2011

39 On acid hydrolysis, which compounds produce propanoic acid? 1 CH3CH2CO2CH3 2 CH3CH2CH2CN 3 CH3CH2CH2Cl

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2011

29 Which pair of substances could react to give the ester CH3CH2CO2CH3? A ethanol and ethanoic acid B methanol and ethanoic acid C methanol and propanoic acid D propan-1-ol and methanoic acid

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2011

22 Use of the Data Booklet is relevant to this question. A sample of ethyl propanoate is hydrolysed by heating under reflux with aqueous sodium hydroxide. The two organic products of the hydrolysis are separated, purified and weighed. Out of the total mass of products obtained, what is the percentage by mass of each product? A 32.4 % and 67.6 % B 38.3 % and 61.7 % C 42.3 % and 57.7 % D 50.0 % and 50.0 %

1 marks

Answer: A

This question in 9701/11 May/June 2012

23 Compound C is used in textile and leather processing. O O C CH2 compound C H2C C O O Which starting material(s), on gentle heating with a few drops of concentrated sulfuric acid, generates compound C? A CH3COOH only B HOCH2COOH only C CH3COOCH2COOH only D CH3COOH mixed with HOCH2COOH

1 marks

Answer: B

This question in 9701/11 May/June 2012

24 How many isomeric esters have the molecular formula C4H8O2? A 2 B 3 C 4 D 5

1 marks

Answer: C

This question in 9701/11 May/June 2012

20 Use of the Data Booklet is relevant to this question. A sample of propyl ethanoate is hydrolysed by heating under reflux with aqueous sodium hydroxide. The two organic products of the hydrolysis are separated, purified and weighed. Out of the total mass of products obtained, what is the percentage by mass of each product? A 32.4 % and 67.6 % B 38.3 % and 61.7 % C 42.3 % and 57.7 % D 50.0 % and 50.0 %

1 marks

Answer: C

This question in 9701/12 May/June 2012

27 A compound Y has the following properties. • It is a liquid at room temperature and atmospheric pressure. • It does not mix completely with water. • It does not give steamy fumes with PCl5. What could Y be? A ethane B ethanoic acid C ethanol D ethyl ethanoate

1 marks

Answer: D

This question in 9701/12 May/June 2012

22 Compound C is used in textile and leather processing. O O C CH2 compound C H2C C O O Which starting material(s), on gentle heating with a few drops of concentrated sulfuric acid, generates compound C? A CH3COOH only B HOCH2COOH only C CH3COOCH2COOH only D CH3COOH mixed with HOCH2COOH

1 marks

Answer: B

This question in 9701/13 May/June 2012

23 How many isomeric esters have the molecular formula C4H8O2? A 2 B 3 C 4 D 5

1 marks

Answer: C

This question in 9701/13 May/June 2012

24 Use of the Data Booklet is relevant to this question. A sample of ethyl propanoate is hydrolysed by heating under reflux with aqueous sodium hydroxide. The two organic products of the hydrolysis are separated, purified and weighed. Out of the total mass of products obtained, what is the percentage by mass of each product? A 32.4 % and 67.6 % B 38.3 % and 61.7 % C 42.3 % and 57.7 % D 50.0 % and 50.0 %

1 marks

Answer: A

This question in 9701/13 May/June 2012

30 Compound X, C6H12O, is oxidised by acidified sodium dichromate(VI) to compound Y. Compound Y reacts with ethanol in the presence of a little concentrated sulfuric acid to give liquid Z. What is the formula of Z? A CH3(CH2)4COCH2CH3 B CH3(CH2)4CO2CH2CH3 C CH3CH2CO2(CH2)4CH3 D CH3CO2(CH2)5CH3

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2012

30 Compound X, C6H12O, is oxidised by acidified sodium dichromate(VI) to compound Y. Compound Y reacts with ethanol in the presence of a little concentrated sulfuric acid to give liquid Z. What is the formula of Z? A CH3(CH2)4COCH2CH3 B CH3(CH2)4CO2CH2CH3 C CH3CH2CO2(CH2)4CH3 D CH3CO2(CH2)5CH3

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2012

20 An organic compound X ● is unaffected by hot acidified potassium manganate(VII), ● reacts with ethanoic acid in the presence of concentrated sulfuric acid. What is compound X? A CH3CO2C2H5 B CH3CH2COCH3 C (CH3)3COH D CH3CH2CHOHCH3

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2012

23 Bees use 2-methylbutyl ethanoate as an ‘alarm’ pheromone to alert other bees. H O H C C H H H H H O C C C C H H H H H C H H 2-methylbutyl ethanoate Which starting materials would be required to synthesise 2-methylbutyl ethanoate? A CH3CH2OH and CH3CH2CH(CH3)CO2H B CH3CO2H and CH3CH2CH(CH3)CH2OH C CH3CH2OH and CH3CH2CH(CH3)CH2CO2H D CH3CO2H and CH3CH2CH(CH3)CH2CO2H

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2012

6 An experiment is set up to measure the rate of hydrolysis of ethyl ethanoate. CH3CO2C2H5 + H2O CH3CO2H + C2H5OH The hydrolysis is found to be slow in neutral aqueous solution but it proceeds at a measurable rate when the solution is acidified with hydrochloric acid. What is the function of the hydrochloric acid? A to dissolve the ethyl ethanoate B to ensure that the reaction reaches equilibrium C to increase the reaction rate by catalytic action D to suppress ionisation of the ethanoic acid formed

1 marks

Answer: C

This question in 9701/11 May/June 2013

21 Lactic acid (2-hydroxypropanoic acid), CH3CH(OH)CO2H, is found in sour milk. Which reaction could occur with lactic acid? A CH3CH(OH)CO2H + CH3OH → CH3CH(OCH3)CO2H + H2O B CH3CH(OH)CO2H + HCO2H → CH3CH(O2CH)CO2H + H2O C CH3CH(OH)CO2H + NaHCO3 → CH3CH(ONa)CO2H + H2O + CO2 D CH3CH(OH)CO2H + Cl 2 → CH3CH(Cl )CO2H + HOCl

1 marks

Answer: B

This question in 9701/11 May/June 2013

28 The structural formula of a compound X is shown below. O CH3CH2CH2OC H What is the name of compound X and how does its boiling point compare with that of butanoic acid? name of X boiling point of X A methyl propanoate higher B methyl propanoate lower C propyl methanoate higher D propyl methanoate lower

1 marks

Answer: D

This question in 9701/11 May/June 2013

30 Some vegetable oils contain ‘trans fats’ that are associated with undesirable increases in the amount of cholesterol in the blood. In the diagrams below, R1 and R2 are different hydrocarbon chains. Which diagram correctly illustrates an optically active ‘trans fat’? A B H R1CO2CH2 H R1CO2CH2 CH3(CH2)6C C(CH2)7CO2CH CH3(CH2)6C C(CH2)7CO2CH H R1CO2CH2 H R2CO2CH2 C D H H R1CO2CH2 H H R1CO2CH2 CH3(CH2)6C C(CH2)7CO2CH CH3(CH2)6C C(CH2)7CO2CH R1CO2CH2 R2CO2CH2

1 marks

Answer: B

This question in 9701/11 May/June 2013

39 A sun protection cream contains the following ester as its active ingredient. CH2CH3 CH3O CH CHCO2CH2CH CH2CH2CH2CH3 Which substances are present in the products of its hydrolysis by aqueous sodium hydroxide? 1 CH3CH2CH2CH2CH(CH2CH3)CH2OH 2 CH3O CH CHCO2 –Na+ 3 CH3O CO2 –Na+

1 marks

Answer: B

This question in 9701/11 May/June 2013

29 Compound Y has Mr of 88. It does not fizz when added to a solution of sodium hydrogencarbonate. It can be hydrolysed by dilute sulfuric acid to produce two organic products with Mr values of 46 and 60. What is the identity of compound Y? A butanoic acid B ethyl ethanoate C 3-hydroxybutanal D butyl methanoate

1 marks

Answer: B

This question in 9701/12 May/June 2013

29 How many isomeric esters, including structural isomers and stereoisomers, can be made with the molecular formula C5H10O2, if methanoic acid is one of the two reactants used? A 2 B 3 C 4 D 5

1 marks

Answer: D

This question in 9701/13 May/June 2013

29 How many of the compounds shown will react with aqueous sodium hydroxide to form the sodium salt of a carboxylic acid? H3C O H O C CH2 CH3 C CH2 CH3 O O O O H C H3C CH C O CH2 CH2 CH3 CH3 O H A 1 B 2 C 3 D 4

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2013

29 How many of the compounds shown will react with aqueous sodium hydroxide to form the sodium salt of a carboxylic acid? H3C O H O C CH2 CH3 C CH2 CH3 O O O O H C H3C CH C O CH2 CH2 CH3 CH3 O H A 1 B 2 C 3 D 4

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2013

28 Compound X reacts with ethanoic acid in the presence of an H+ catalyst to produce the compound below. O H H O H3C C C C O C CH3 H H What is the molecular formula of compound X? A C2H6O2 B C2H6O3 C C4H8O D C4H8O2

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2013

22 An ester with an odour of banana has the following formula. CH3CO2CH2CHCH2CH3 CH3 Which pair of reactants, under suitable conditions, will produce this ester? A CH3CH2CHCH2CO2H + CH3OH CH3 B CH3CH2CHCO2H + CH3CH2OH CH3 C CH3CO2H + CH3CH2CHCH2OH CH3 D CH3CO2H + CH3CHCH2CH2OH CH3

1 marks

Answer: C

This question in 9701/11 May/June 2014

38 The molecule responsible for the pineapple flavour used in sweets is CH3CH2CH2CO2CH2CH3. Which statements about this molecule are correct? 1 The name of this compound is ethyl butanoate. 2 This compound is a structural isomer of hexanoic acid. 3 When this compound is heated with aqueous sodium hydroxide, the products are butan-1-ol and sodium ethanoate.

1 marks

Answer: B

This question in 9701/11 May/June 2014

23 An ester of structural formula CH3CO2CH3 is heated with an aqueous solution of sodium hydroxide. What are the two organic products of this reaction? A ethanoic acid and methanol B methanoic acid and ethanol C sodium ethanoate and methanol D sodium methanoate and ethanol

1 marks

Answer: C

This question in 9701/12 May/June 2014

28 The diagram shows the structure of ethanedioic acid. HO OH C C O O Ethanedioic acid reacts with ethanol in the presence of a few drops of concentrated sulfuric acid to form a diester. The molecular formula of the diester is C6H10O4. What is the structural formula of the diester? A CH3CH2CO2CO2CH2CH3 B CH3CH2OCOCO2CH2CH3 C CH3CH2O2CO2CCH2CH3 D CH3CO2CH2CH2OCOCH3

1 marks

Answer: B

This question in 9701/12 May/June 2014

20 Diesters can be made from diacids such as propane-1,3-dioic acid, HO2CCH2CO2H. Which combination of reactants would form the diester CH3CH2OCOCH2CH2CO2CH2CH3? A butane-1,4-dioic acid and ethanol B ethanedioic acid and propan-1-ol C ethanedioic acid, ethanol and butan-1-ol D propane-1,3-dioic acid, ethanol and propan-1-ol

1 marks

Answer: A

This question in 9701/13 May/June 2014

28 The compound cetyl palmitate, C15H31CO2C16H33, is a waxy solid. When cetyl palmitate is heated under reflux with an excess of aqueous sodium hydroxide, which products will be formed? A C15H31ONa and C16H33CO2Na B C15H31CO2Na and C16H33ONa C C15H31OH and C16H33CO2Na D C15H31CO2Na and C16H33OH

1 marks

Answer: D

This question in 9701/13 May/June 2014

28 The ester CH3CH2CH2CO2CH3 is responsible for the aroma of apples. When this ester is hydrolysed by acid in the stomach, what is the empirical formula of the organic acid produced? A CH2O B CH4O C C2H4O D C3H6O2

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2014

28 The ester CH3CH2CH2CO2CH3 is responsible for the aroma of apples. When this ester is hydrolysed by acid in the stomach, what is the empirical formula of the organic acid produced? A CH2O B CH4O C C2H4O D C3H6O2

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2014

24 Compound X can be made from 2-hydroxybutanoic acid. O H C C O CH3CH2 CH2CH3 O C C H O compound X What should be heated with 2-hydroxybutanoic acid in order to make compound X? A acidified potassium dichromate(VI) B aluminium oxide C concentrated sulfuric acid D dilute sodium hydroxide

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2014

26 Pheromones are used by insects and other animals as a means of communication. The pheromone in a bee sting is 3-methylbutyl ethanoate. O CH3 C O CH2CH2CH(CH3)2 3-methylbutyl ethanoate What are the organic products when 3-methylbutyl ethanoate is heated under reflux with aqueous sodium hydroxide? A CH3CO2H and (CH3)2CHCH2CH2OH B CH3CO2H and (CH3)2CHCH2CH2O–Na+ C CH3CO2 –Na+ and (CH3)2CHCH2CH2OH D CH3CO2 –Na+ and (CH3)2CHCH2CH2O–Na+

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2014

30 Methyl butanoate, C5H10O2, is an ester used in the food industry to give products the flavour of apples. O H H H H C C C C H H C O H H H H methyl butanoate Including methyl butanoate, how many structural isomers are there of C5H10O2 that are esters? A 6 B 8 C 9 D 10

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2014

30 The drug Sirolimus is used to treat patients after kidney transplants. OH H3C O CH3 N O H H H O O O O H3C O H3C HO OH H3C H CH3 O O O H3C H3C CH3 CH3 Sirolimus On reaction with hot aqueous sodium hydroxide, Sirolimus produces an equimolar mixture of two organic products. What is the structural formula of the product with the lower relative molecular mass? A B C D N N CO2Na N N CO2Na H H CO2Na CO2Na

1 marks

Answer: B

This question in 9701/12 May/June 2015

20 Which ester is formed when the alcohol CH3CH2OH is reacted with CH3CH2CH2CO2H? A butyl ethanoate B ethyl butanoate C ethyl propanoate D propyl ethanoate

1 marks

This question in 9701/12 Oct/Nov 2015

27 The fragrance compounds of perfumes are often dissolved in solvent Y, which has a molecular formula C7H12O4. It is made by reacting propane-1,2-diol with ethanoic acid in the presence of an acid catalyst. H CH3 HO C C OH H H propane-1,2-diol What is the structure of solvent Y? A B O H CH3 O O H CH3 O C O C C C C C C C H3C H H O CH3 H3C O H H O CH3 C D O H CH3 O O H CH3 O C C C O C C O C C O C H3C O H H CH3 H3C H H CH3

1 marks

Answer: D

This question in 9701/12 Feb/March 2016

28 Which mixture could be used to produce propyl methanoate? A CH3CH2CO2H and CH3OH B CH3CH2CH2CH2OH and HCO2H C CH3CH2CH2OH and HCO2H D CH3CH2CH2CO2H and CH3OH

1 marks

Answer: C

This question in 9701/12 Feb/March 2016

30 Which row of the table is correct? increasing number of carbon atoms A ethyl methanoate methyl propanoate pentyl pentanoate propyl butanoate B ethyl methanoate methyl propanoate propyl butanoate pentyl pentanoate C methyl propanoate propyl butanoate ethyl methanoate pentyl pentanoate D propyl butanoate ethyl methanoate pentyl pentanoate methyl propanoate

1 marks

Answer: B

This question in 9701/12 Feb/March 2016

21 The structural formula of compound X is shown below. O CH3CH2CH2OC H compound X What is the name of compound X and how does its boiling point compare with that of butanoic acid? name of X boiling point of X A methyl propanoate higher than butanoic acid B methyl propanoate lower than butanoic acid C propyl methanoate higher than butanoic acid D propyl methanoate lower than butanoic acid

1 marks

Answer: D

This question in 9701/11 May/June 2016

27 Cyclic esters are also known as lactones. Delta lactone is used as a solvent and in the manufacture of polyesters. O O delta lactone From which compound could delta lactone be made by a single reaction? A HOCH2CH2CH2CH2CHO B HOCH2CH2CH2CH2CO2H C HOCH2CH2CH2CH2CH2OH D HOCH2CH2CH2CH2CH2CO2H

1 marks

Answer: B

This question in 9701/11 May/June 2016

29 The ester CH3CH2CH2CO2CH2CH(CH3)2 was hydrolysed under acidic conditions. What are the organic products of this hydrolysis? A butanoic acid and 2-methylpropan-1-ol B butanoic acid and 2-methylpropan-2-ol C butan-1-ol and 2-methylpropanoic acid D propanoic acid and 2-methylpropan-1-ol

1 marks

Answer: A

This question in 9701/11 May/June 2016

40 The diagram shows the structure of an addition polymer, X. CH3 H CH3 H CH3 H C C C C C C H CO2CH3 H CO2CH3 H CO2CH3 Which reagents react with polymer X? 1 aqueous sulfuric acid 2 aqueous sodium hydroxide 3 sodium

1 marks

Answer: B

This question in 9701/11 May/June 2016

29 How many isomeric esters, including structural isomers and stereoisomers, can be made with the molecular formula C5H10O2, if methanoic acid is one of the two reactants used? A 2 B 3 C 4 D 5

1 marks

Answer: D

This question in 9701/12 May/June 2016

22 An ester with an aroma of pineapples can be synthesised in the laboratory from butanal using this reaction scheme. X NaBH4 conc. H2SO4 CH3(CH2)2CHO ester Cr2O7 2– / H+ Y What is the structural formula of the ester? A CH3(CH2)2CO2(CH2)2CH3 B CH3(CH2)2CO2(CH2)3CH3 C CH3(CH2)3CO2(CH2)2CH3 D CH3(CH2)3CO2(CH2)3CH3

1 marks

Answer: B

This question in 9701/13 May/June 2016

29 The ester, CH3CH2CO2CH3, is hydrolysed by boiling with aqueous sodium hydroxide. Which compound is one of the products? A ethanol B propan-1-ol C sodium methanoate D sodium propanoate

1 marks

Answer: D

This question in 9701/13 May/June 2016

40 The structural formulae of two compounds are shown below. O O CH3CH2CH2CH2CH2C CH3CH2CH2CH2CH2OC OH H Which statements about these compounds are correct? 1 The two compounds are structural isomers of each other. 2 The empirical formula of both compounds is C3H6O. 3 Both compounds are carboxylic acids.

1 marks

Answer: B

This question in 9701/13 May/June 2016

23 Part of the structure of a fungicide, strobilurin, is shown. R and R' are inert groups. O OCH3 R' R strobilurin In this reaction, strobilurin is warmed with aqueous sulfuric acid producing compound X. Compound X is then treated with hydrogen in the presence of a nickel catalyst producing compound Y. What could be the structure of compound Y? A B O OH HO OCH3 R' R' R R C D OH O OH OH OH R' R' R R OH

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2016

29 Which formula represents an ester that will form propanoic acid on hydrolysis with dilute sulfuric acid? A B C D O O O O O O O O

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2016

30 A solvent, X, used in printing inks has a molecular formula C6H10O4. It may be made by reacting ethane-1,2-diol with ethanoic acid in the presence of an acid catalyst. H H HO C C OH H H ethane-1,2-diol What is the structure of solvent X? A B H H O O H H O HO C C O C C O C C O C H H CH3 H3C H H CH3 C D O H H O O H H O C C C C C C C O C H3C O H H O CH3 H3C O H H CH3

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2016

23 Part of the structure of a fungicide, strobilurin, is shown. R and R' are inert groups. O OCH3 R' R strobilurin In this reaction, strobilurin is warmed with aqueous sulfuric acid producing compound X. Compound X is then treated with hydrogen in the presence of a nickel catalyst producing compound Y. What could be the structure of compound Y? A B O OH HO OCH3 R' R' R R C D OH O OH OH OH R' R' R R OH

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2016

29 Which formula represents an ester that will form propanoic acid on hydrolysis with dilute sulfuric acid? A B C D O O O O O O O O

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2016

30 A solvent, X, used in printing inks has a molecular formula C6H10O4. It may be made by reacting ethane-1,2-diol with ethanoic acid in the presence of an acid catalyst. H H HO C C OH H H ethane-1,2-diol What is the structure of solvent X? A B H H O O H H O HO C C O C C O C C O C H H CH3 H3C H H CH3 C D O H H O O H H O C C C C C C C O C H3C O H H O CH3 H3C O H H CH3

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2016

28 A carboxylic acid, P, has no possible chain isomers. It reacts with an alcohol, Q, that has only one positional isomer. What could be the ester formed from a reaction between P and Q? A butyl propanoate B ethyl butanoate C pentyl ethanoate D propyl pentanoate

1 marks

Answer: A

This question in 9701/12 May/June 2017

30 How many esters with the molecular formula C5H10O2 can be made by reacting a primary alcohol with a carboxylic acid? A 4 B 5 C 6 D 8

1 marks

Answer: C

This question in 9701/13 May/June 2017

39 Substance M is refluxed with aqueous sodium hydroxide. One of the products of this reaction reacts with alkaline aqueous iodine to give a pale yellow precipitate. Which compounds could be substance M? 1 CH3CO2CH3 2 CH3CO2CH2CH3 3 HCO2CH(CH3)2

1 marks

Answer: C

This question in 9701/13 May/June 2017

30 A sample of the ester CH3CH2CH2CO2CH2CH3 is hydrolysed. The product mixture is then treated with hot, acidified KMnO4. What are the final carbon-containing products? A CH3CH2CO2H only B CH3CO2H + CH3CH2CO2H C CH3CO2H + CH3CH2CH2CO2H D CH3CH2OH + CH3CH2CH2CO2H

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2017

30 An ester with an odour of banana has the following formula. CH3CO2CH2CHCH2CH3 CH3 Which pair of reactants, under suitable conditions, will produce this ester? A CH3CH2CHCH2CO2H + CH3OH CH3 B CH3CH2CHCO2H + CH3CH2OH CH3 C CH3CO2H + CH3CH2CHCH2OH CH3 D CH3CO2H + CH3CHCH2CH2OH CH3

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2017

30 A sample of the ester CH3CH2CH2CO2CH2CH3 is hydrolysed. The product mixture is then treated with hot, acidified KMnO4. What are the final carbon-containing products? A CH3CH2CO2H only B CH3CO2H + CH3CH2CO2H C CH3CO2H + CH3CH2CH2CO2H D CH3CH2OH + CH3CH2CH2CO2H

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2017

11 Hydrogen ions catalyse the hydrolysis of esters. Which statement is correct? A The hydrogen ions act as a heterogeneous catalyst. B The hydrogen ions are in the same phase as the reactants. C The hydrogen ions are used up in the reaction. D The hydrogen ions have no effect on the activation energy of the reaction.

1 marks

Answer: B

This question in 9701/11 May/June 2018

27 Ethyl propanoate is refluxed with aqueous sodium hydroxide. The alcohol produced is then reacted with methyl propanoic acid to make a second ester. What is the structural formula of this second ester? A B O O CH3 CH2 O C CH CH3 CH3 CH2 CH2 O C CH CH3 CH3 CH3 C D O O CH3 C O CH2 CH CH3 CH3 CH2 C O CH2 CH CH3 CH3 CH3

1 marks

Answer: A

This question in 9701/11 May/June 2018

28 Ethanal, CH3CHO, is used to make product R in a three-stage synthesis. HCN H2SO4(aq), conc. H2SO4 / NaCN reflux (a few drops) CH3CHO product P product Q product R Two molecules of Q react to give one molecule of R plus two molecules of water. R has two ester functional groups in each molecule. R does not react with sodium. What is the empirical formula of R? A CHO B C3H4O2 C C3H5O2 D C6H10O5

1 marks

Answer: B

This question in 9701/12 May/June 2018

29 The ester ethyl butanoate can be hydrolysed using an excess of dilute sodium hydroxide solution. Which substance is a product of this reaction? A CH3CH2CH2CO2Na B CH3CO2Na C CH3CH2ONa D H2O

1 marks

Answer: A

This question in 9701/12 May/June 2018

40 The ester C2H5CO2CH2CH2CH3 can be made in a school or college laboratory by a sequence of four reactions or fewer using compound Z as the only organic material. What might be the identity of compound Z? 1 CH3CH2CH2OH 2 CH3CH2CHO 3 CH3COCH3

1 marks

Answer: B

This question in 9701/12 May/June 2018

29 An ester X has the structural formula CH3CO2CH(CH3)CH2CH3. X can be prepared by heating an alcohol Y, under reflux, with ethanoic acid and an acid catalyst. What is the correct name for Y? A butan-1-ol B butan-2-ol C butan-3-ol D methylpropan-2-ol

1 marks

Answer: B

This question in 9701/13 May/June 2018

29 The diester shown can be hydrolysed by heating with an excess of aqueous sodium hydroxide. O H H H H H C O C C C O C C H H H H O H What would the products of this reaction be? O H H H O H A H C HO C C C OH HO C C H OH H H H H O H H H O H B H C NaO C C C ONa HO C C H OH H H H H O H H H O H C H C HO C C C OH NaO C C H ONa H H H H O H H H O H D H C NaO C C C ONa NaO C C H ONa H H H H

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2018

26 The reactions of four organic compounds are given in the table. Which compound could be propan-2-ol? reagent / observations when oxidised with Cr2O7 2– / H+, gives when added to ethanoic acid, and a an organic product with a boiling point few drops of conc. H2SO4, gives a greater than the original compound sweet-smelling compound A no no B no yes C yes no D yes yes

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2018

28 Compound Y gives methanol and sodium ethanoate on treatment with aqueous sodium hydroxide. What is the structure of Y? A CH3CO2CH3 B HCO2C2H5 C HO2CCH2CHO D HOCH2CH2COOH

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2018

29 The diester shown can be hydrolysed by heating with an excess of aqueous sodium hydroxide. O H H H H H C O C C C O C C H H H H O H What would the products of this reaction be? O H H H O H A H C HO C C C OH HO C C H OH H H H H O H H H O H B H C NaO C C C ONa HO C C H OH H H H H O H H H O H C H C HO C C C OH NaO C C H ONa H H H H O H H H O H D H C NaO C C C ONa NaO C C H ONa H H H H

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2018

40 Carboxylic acids react with alcohols to produce esters. Carboxylic acid X forms one ester only with molecular formula C5H10O2. What could X be? 1 ethanoic acid 2 propanoic acid 3 butanoic acid

1 marks

Answer: C

This question in 9701/11 May/June 2019

29 One molecule of compound R is shown. compound R H H H O H C C C O C H H H H What is the name of compound R and how does its boiling point compare with that of butanoic acid? name of R boiling point of R A methyl propanoate higher than butanoic acid B methyl propanoate lower than butanoic acid C propyl methanoate higher than butanoic acid D propyl methanoate lower than butanoic acid

1 marks

Answer: D

This question in 9701/12 May/June 2019

29 Which pair of substances could react to give the ester CH3CH2CO2CH3? A ethanol and ethanoic acid B methanol and ethanoic acid C methanol and propanoic acid D propan-1-ol and methanoic acid

1 marks

Answer: C

This question in 9701/13 May/June 2019

30 An ester is shown. O O O H O What is the structure of the carboxylic acid that would be obtained by acid hydrolysis of the ester linkage? A B O O OH O O H OH HO O C D O O O O O O O OH HO O

1 marks

Answer: A

This question in 9701/13 May/June 2019

29 When CH2(OH)CH=CHCO2H is warmed with a little concentrated sulfuric acid, a cyclic compound is formed. What is the skeletal formula of the cyclic compound? A B C D O O O O O O O O O

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2019

28 Esters can be prepared by the reaction of a carboxylic acid with an alcohol in the presence of concentrated sulfuric acid. Which row gives the correct names of the reagents that would be suitable to prepare ester Z? Z O O alcohol carboxylic acid A butan-1-ol methyl propanoic acid B propan-1-ol butanoic acid C propan-2-ol butanoic acid D propan-2-ol propanoic acid

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2019

29 Compound Q can be hydrolysed by HCl (aq). The two products of this hydrolysis have the same empirical formula. What could Q be? A CH3CO2CH2CH2OH B CH3CO2CH2CH2CO2H C CH3CH2CO2CH2CH2CH3 D CH3CH2CH(OH)CH(OH)CH2CH3

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2019

29 When CH2(OH)CH=CHCO2H is warmed with a little concentrated sulfuric acid, a cyclic compound is formed. What is the skeletal formula of the cyclic compound? A B C D O O O O O O O O O

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2019

22 The diagram shows the structure of ethanedioic acid. HO OH C C O O Ethanedioic acid reacts with ethanol in the presence of a few drops of concentrated sulfuric acid to form a diester. The molecular formula of the diester is C6H10O4. What is the structural formula of the diester? A CH3CH2CO2CO2CH2CH3 B CH3CH2OCOCO2CH2CH3 C CH3CH2O2CO2CCH2CH3 D CH3CO2CH2CH2OCOCH3

1 marks

Answer: B

This question in 9701/12 Feb/March 2020

30 The diagram shows the structure of compound Q. Q O O X HO Y O O Two of the rings, X and Y, contain a C=C bond. Which row is correct? number of ester groups description of in one molecule of Q rings X and Y A 1 both are planar B 1 neither is planar C 2 both are planar D 2 neither is planar

1 marks

Answer: D

This question in 9701/12 Feb/March 2020

26 When compound X is heated under reflux with aqueous sodium hydroxide solution two products are formed: sodium ethanoate and hexan-1-ol. What is compound X? A B C D O O O O O O O O

1 marks

Answer: D

This question in 9701/11 May/June 2020

29 Compound X has the infra-red spectrum shown. 100 transmittance / % 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 What could be the identity of compound X? A ethanoic acid B ethanol C ethylethanoate D propanone

1 marks

Answer: A

This question in 9701/11 May/June 2020

23 Ester X is shown. ester X CH3CO2(CH2)7CH3 Ester X is hydrolysed using aqueous sodium hydroxide. What is the molecular formula of one of the products? A C2H4O2 B C2H3O2Na C C8H16O D C8H17O2Na

1 marks

Answer: B

This question in 9701/12 May/June 2020

27 How many isomeric esters have the molecular formula C4H8O2? A 2 B 3 C 4 D 5

1 marks

Answer: C

This question in 9701/12 May/June 2020

21 Ester P has the following structural formula. ester P O CH3C OCH2CH2CH(CH3)2 Which compounds are produced when P is hydrolysed using dilute hydrochloric acid? A CH3COCl and (CH3)2CHCH2CH2OH B CH3CH2OH and (CH3)2CHCH2CO2H C CH3CO2H and (CH3)2CHCH2CO2H D CH3CO2H and (CH3)2CHCH2CH2OH

1 marks

Answer: D

This question in 9701/13 May/June 2020

29 The ester ethyl methanoate is prepared in a school laboratory by reacting a carboxylic acid with an alcohol. During the reaction, only 50.0% of the alcohol is converted into the ester. Which mass of alcohol is needed to prepare 10.0 g of the ester? A 3.11 g B 8.65 g C 12.4 g D 32.2 g

1 marks

Answer: C

This question in 9701/13 May/June 2020

40 Which pairs are structural isomers of each other? 1 CH3CH2CH2CH2CH2CO2H and CH3CH2CH2CO2CH2CH3 2 and 3 CH3CH2CH2CH(OH)CH2CH3 and CH3CH2CH(OH)CH2CH2CH3

1 marks

Answer: B

This question in 9701/13 May/June 2020

39 Three reactions of primary alcohols are listed. Which reactions give water as one of the products? 1 reaction with ethanoic acid 2 reaction with concentrated HBr 3 passing the alcohol vapour over heated Al 2O3

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2020

40 The diagram shows part of the structure of polymer X. CH3 H CH3 H CH3 H C C C C C C H CO2CH3 H CO2CH3 H CO2CH3 Which reagents react with polymer X? 1 aqueous sulfuric acid 2 aqueous sodium hydroxide 3 sodium

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2020

39 Three reactions of primary alcohols are listed. Which reactions give water as one of the products? 1 reaction with ethanoic acid 2 reaction with concentrated HBr 3 passing the alcohol vapour over heated Al 2O3

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2020

23 Part of the structure of strobilurin is shown. R and R' are inert groups. strobilurin O OCH3 R' R Strobilurin is warmed with aqueous sulfuric acid producing compound X. Compound X is then treated with hydrogen in the presence of a nickel catalyst producing compound Y. What could be the structure of compound Y? A B O OH HO OCH3 R' R' R R C D OH O OH OH OH R' R' R R OH

1 marks

Answer: A

This question in 9701/12 Feb/March 2021

29 Which reaction gives butanoic acid as one of its products? A acid hydrolysis of butyl ethanoate B alkaline hydrolysis of butyl ethanoate C acid hydrolysis of ethyl butanoate D alkaline hydrolysis of ethyl butanoate

1 marks

Answer: C

This question in 9701/12 Feb/March 2021

38 An excess of P reacts with Q, in the presence of concentrated sulfuric acid, to form R. Effervescence is seen when a piece of sodium is added to pure R. The structure of P is shown. P O OH OH Which organic compounds could be compound Q? O 1 OH 2 OH 3 O

1 marks

Answer: B

This question in 9701/12 Feb/March 2021

24 The compound cetyl palmitate, C15H31CO2C16H33, is a waxy solid. Cetyl palmitate is heated under reflux with an excess of aqueous sodium hydroxide. Which products will be formed? A C15H31ONa and C16H33CO2Na B C15H31CO2Na and C16H33ONa C C15H31OH and C16H33CO2Na D C15H31CO2Na and C16H33OH

1 marks

Answer: D

This question in 9701/11 May/June 2021

40 Propanoic acid is reacted with an excess of lithium aluminium hydride. The organic product of this reaction is reacted with ethanoic acid in the presence of concentrated sulfuric acid, forming product X. What are major commercial uses of X? 1 fuel 2 solvent 3 flavouring

1 marks

Answer: C

This question in 9701/11 May/June 2021

22 Compound X can be converted into compound Y in a single step. compound Y OH X O O What could be the identity of X? A B C D

1 marks

Answer: A

This question in 9701/12 May/June 2021

29 Two reactions are shown. LiAl H4 (CH3)2CHCO2H alcohol P hydrolysis CH3CO2CH(CH3)2 alcohol Q + acid R To which classes of alcohol do P and Q belong? P Q A primary primary B primary secondary C secondary primary D secondary secondary

1 marks

Answer: B

This question in 9701/13 May/June 2021

30 The infra-red spectrum of molecule Z is shown. 100 transmittance / % 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 What could be the identity of Z? A B HO OH O O HO O O O C D O O O O O O

1 marks

Answer: D

This question in 9701/13 May/June 2021

29 The structural formula of an ester is (CH3)2CHOCO(CH2)2CH3. This ester is boiled with aqueous hydrochloric acid. Which two products are formed? A propan-1-ol and butanoic acid B propan-2-ol and butanoic acid C propan-1-ol and propanoic acid D propan-2-ol and propanoic acid

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2021

40 Which reactions of propan-1-ol have water as one of the products? 1 passing propan-1-ol vapour over hot Al 2O3 2 mixing propan-1-ol with warm ethanoic acid and a few drops of concentrated sulfuric acid 3 warming propan-1-ol with HBr

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2021

40 Ethyl butanoate is heated with a dilute aqueous solution of sodium hydroxide. Which substances are products of this reaction? 1 sodium butanoate 2 water 3 sodium ethanoate

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2021

29 The structural formula of an ester is (CH3)2CHOCO(CH2)2CH3. This ester is boiled with aqueous hydrochloric acid. Which two products are formed? A propan-1-ol and butanoic acid B propan-2-ol and butanoic acid C propan-1-ol and propanoic acid D propan-2-ol and propanoic acid

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2021

40 Which reactions of propan-1-ol have water as one of the products? 1 passing propan-1-ol vapour over hot Al 2O3 2 mixing propan-1-ol with warm ethanoic acid and a few drops of concentrated sulfuric acid 3 warming propan-1-ol with HBr

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2021

28 How many esters have the molecular formula C4H8O2? A 2 B 3 C 4 D 5

1 marks

Answer: C

This question in 9701/11 May/June 2022

37 Which compound produces butan-2-ol and ethanoic acid on hydrolysis? A CH3CO2CH(CH3)2 B CH3CO2CH(CH3)CH2CH3 C CH3CH(CH3)CO2CH2CH3 D CH3CH2CO2CH(CH3)CH2CH3

1 marks

Answer: B

This question in 9701/11 May/June 2022

35 The skeletal formula of M is shown. M O OH HO O M is reacted with an excess of LiAl H4. Dilute acid is then added. What is the molecular formula of the final organic product? A C5H6O5 B C5H10O4 C C5H10O3 D C5H12O3

1 marks

Answer: D

This question in 9701/12 May/June 2022

38 Ethyl butanoate is a flavouring, with a fruity flavour. Which row is correct? alcohol and acid that react the mass of water formed to form ethyl butanoate when 2.32 g of ester is formed O A and OH 0.36 g OH O B and OH 0.40 g OH O C and OH 0.36 g OH O D and OH 0.40 g OH

1 marks

Answer: A

This question in 9701/12 May/June 2022

37 An ester is shown. H H H O H C H H C C C H H H O C C H H H C H H Which two compounds react to form this ester? A 2-methylpropan-1-ol and propanoic acid B 2-methylpropan-2-ol and propanoic acid C propan-1-ol and 2-methylpropanoic acid D 2-methylpropan-2-ol and ethanoic acid

1 marks

Answer: B

This question in 9701/13 May/June 2022

32 An alcohol, X, reacts with a dicarboxylic acid, Y, to form a double ester, Z. The diagram shows the structure of the ester. Z O O O O Which row about the reactants forming ester Z is correct? the class of the shape of alcohol X the ring in Y A secondary non-planar B secondary planar C tertiary non-planar D tertiary planar

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2022

27 A carboxylic acid, P, has no chain isomers. It reacts with an alcohol, Q, that has only one positional isomer. What could be the ester formed from a reaction between P and Q? A butyl propanoate B ethyl butanoate C pentyl ethanoate D propyl pentanoate

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2022

38 The ester CH3CH2CO2CH3 is hydrolysed by boiling with aqueous sodium hydroxide. Which compound is one of the products? A ethanol B propan-1-ol C sodium methanoate D sodium propanoate

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2022

32 An alcohol, X, reacts with a dicarboxylic acid, Y, to form a double ester, Z. The diagram shows the structure of the ester. Z O O O O Which row about the reactants forming ester Z is correct? the class of the shape of alcohol X the ring in Y A secondary non-planar B secondary planar C tertiary non-planar D tertiary planar

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2022

36 Compound X reacts with ethanoic acid in the presence of an H+ catalyst to produce the compound shown. O H H O H3C C C C O C CH3 H H What is the molecular formula of compound X? A C2H4O B C2H6O2 C C4H8O D C4H8O2

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2022

36 Compound Q can be hydrolysed by HCl(aq). The two products of this hydrolysis have the same empirical formula. What could Q be? A CH3CO2CH2CH2OH B CH3CO2CH2CH2CO2H C CH3CH2CO2CH2CH2CH3 D CH3CH2CH(OH)CH(OH)CH2CH3

1 marks

Answer: B

This question in 9701/13 May/June 2023

38 The structure of compound X is shown. X O O What is produced when X is heated with NaOH(aq)? A B ONa OH HO HO O O C D O O HO HO ONa OH

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2023

38 How many esters with the molecular formula C5H10O2 can be made by reacting a primary alcohol with a carboxylic acid? A 4 B 5 C 6 D 8

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2023

39 The diagram shows an ester. It is heated under reflux with an excess of NaOH(aq). O O Which row shows the 2 products of the reaction? product 1 product 2 A O OH OH B O ONa OH C O OH ONa D O ONa ONa

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2023

38 The structure of compound X is shown. X O O What is produced when X is heated with NaOH(aq)? A B ONa OH HO HO O O C D O O HO HO ONa OH

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2023

35 Esters can be hydrolysed with an aqueous alkali or an aqueous acid to form two products. The table compares the two methods. Which row is correct? aqueous alkali aqueous acid A complete conversion to forms an equilibrium mixture with a salt and an organic acid an organic acid and an alcohol B forms an equilibrium mixture complete conversion to with a salt and an organic acid a salt and an alcohol C complete conversion to forms an equilibrium mixture with a salt and an alcohol an organic acid and an alcohol D complete conversion to complete conversion to a salt and an alcohol an organic acid and an alcohol

1 marks

Answer: C

This question in 9701/12 Feb/March 2024

38 Compound X is treated with an excess of dilute aqueous potassium hydroxide. X O O What is the structure of the organic product? A B O O – O OH HO OH C D O O – O OH HO OH

1 marks

Answer: A

This question in 9701/11 May/June 2024

38 The diagrams show the structures of two esters, X and Y, that are formed in ripening apples. ester X ester Y O O O O Which carboxylic acids are formed when these esters are hydrolysed by H2SO4(aq)? ester X ester Y A CH3COOH CH3CH2COOH B CH3COOH CH3CH2CH(CH3)COOH C CH3CH(CH3)CH2COOH CH3CH2COOH D CH3CH(CH3)CH2COOH CH3CH2CH(CH3)COOH

1 marks

Answer: B

This question in 9701/12 May/June 2024

39 An addition polymer is made from monomer Z. monomer Z O CH2 CH C OCH2CH3 What is the structure of the polymer made from this monomer? O A CH CH C n O B CH CH C O n C CH2 CH C O n OCH2CH3 D CH2 CH n C OCH2CH3 O

1 marks

Answer: D

This question in 9701/12 May/June 2024

33 The Mr of compound X is 88. Compound X is heated under reflux with an excess of acidified potassium dichromate(VI) to produce compound Y. Compound Y reacts with compound X under suitable conditions to produce compound Z. The Mr of compound Z is 172. What is compound X? A CH3CH2CHOHCH2CH3 B (CH3)2COHCH2CH3 C (CH3)2CHCHOHCH3 D (CH3)3CCH2OH

1 marks

Answer: D

This question in 9701/13 May/June 2024

35 Which substance reacts with ethanoic acid to give the organic product with the highest Mr? A lithium aluminium hydride B magnesium C potassium carbonate D propan-2-ol

1 marks

Answer: B

This question in 9701/13 May/June 2024

36 A sample of propyl ethanoate is hydrolysed by heating under reflux with aqueous NaOH. The two organic products of the hydrolysis are separated, purified and weighed. Out of the total mass of products obtained, what is the percentage by mass of each product? A 32.4% and 67.6% B 38.3% and 61.7% C 42.3% and 57.7% D 50.0% and 50.0%

1 marks

Answer: C

This question in 9701/13 May/June 2024

26 Compound Z has the molecular formula C4H8O2. Compound Z reacts with propan-1-ol in the presence of concentrated H2SO4. The diagram shows the skeletal formulae of three compounds, S, T and U. S T U O O O O O O What are the possible skeletal formulae of the products of the reaction between compound Z and propan-1-ol? A S and T B U only C S and U D T only

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2024

36 C2H5COOCH3 is reacted with aqueous acid. The products from this reaction are reacted with LiAl H4 to form two molecules Y and Z. What are the identities of molecules Y and Z? A both molecules are C2H5OH B CH3OH and CH3CHOHCH3 C CH3OH and C2H5OH D CH3OH and C2H5CH2OH

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2024

38 Which statement about H2C=C(CH3)CH2CO2CH3 is correct? A It can be hydrolysed to a secondary alcohol. B It can be made using ethanoic acid and a suitable alcohol. C It gives a positive test with alkaline I2(aq). D When treated with hot concentrated acidified KMnO4 it gives CH3COCH2COOH as one product.

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2024

26 Compound Z has the molecular formula C4H8O2. Compound Z reacts with propan-1-ol in the presence of concentrated H2SO4. The diagram shows the skeletal formulae of three compounds, S, T and U. S T U O O O O O O What are the possible skeletal formulae of the products of the reaction between compound Z and propan-1-ol? A S and T B U only C S and U D T only

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2024

34 Skeletal formulae of four organic compounds are shown. O O O N O O 1 2 3 4 Which two compounds when separately heated with dilute sulfuric acid produce propanoic acid as one of the products? A 1 and 2 B 1 and 4 C 2 and 3 D 3 and 4

1 marks

Answer: C

This question in 9701/12 Feb/March 2025

29 Which formula represents the organic compound formed by the reaction of propanoic acid with methanol in the presence of concentrated sulfuric acid as a catalyst? A CH3CH2COCH3 B CH3CH2CO2CH3 C CH3CO2CH2CH3 D CH3CH2CH2CO2CH3

1 marks

Answer: B

This question in 9701/11 May/June 2025

29 An ester, R'CO2R", is hydrolysed in alkaline conditions. R' and R" are different alkyl groups. Which row identifies the two products formed? product 1 product 2 A R'CO2H R"OH B R'CO2 – R"OH C R'CO2H R"O– D R'CO2 – R"O–

1 marks

Answer: B

This question in 9701/12 May/June 2025

34 Propanoic acid reacts with LiAl H4 to give organic product P. Methanoic acid reacts with organic product P, in the presence of a few drops of concentrated sulfuric acid, to give organic product Q. What are the skeletal formulae of the two organic products? organic product P organic product Q O A OH O O B OH O O C O O O D O O

1 marks

Answer: B

This question in 9701/12 May/June 2025

39 An organic compound, T, contains only one functional group. Compound T has the empirical formula C2H4O. Some functional groups are listed. 1 alcohol 2 aldehyde 3 ester 4 ketone Which functional groups are possible for compound T? A 1 and 3 B 1 and 4 C 2 and 3 D 2 and 4

1 marks

Answer: C

This question in 9701/13 May/June 2025

16 Propyl methanoate is hydrolysed with NaOH(aq) at 20 C to form two products, X and Y. Product X is an alcohol. Data from the experiment is shown. time / s [X] / mol dm–3 0 0.000 40 0.004 80 0.007 120 0.010 180 0.015 240 0.019 300 0.022 Which row is correct? average rate of reaction product Y between 240 and 300 s A 5.00  10–5 mol dm–3 s–1 HCOONa B 5.00  10–5 mol dm–3 s–1 HCOOH C 7.33  10–5 mol dm–3 s–1 HCOONa D 7.33  10–5 mol dm–3 s–1 HCOOH

1 marks

Answer: A

This question in 9701/14 May/June 2025

36 Structural isomerism and stereoisomerism should be considered when answering this question. How many isomeric esters of methanoic acid can be made with the molecular formula C5H10O2? A 2 B 3 C 4 D 5

1 marks

Answer: D

This question in 9701/14 May/June 2025

35 Which compound is a product of the hydrolysis of CH3CO2CH2C2H5 using aqueous sodium hydroxide? A CH3CO2 –Na+ B CH3CO2H C C2H5CH2O–Na+ D C2H5CH2CO2 –Na+

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2025

37 The table shows the reagents and products of three reactions. reagents products 1 ethanoic acid + Na2CO3 CH3CO2Na + H2O + CO2 2 ethanoic acid + Mg (CH3CO2)2Mg + H2O 3 ethanoic acid + CH3OH CH3CO2CH3 + H2O Which rows are correct? A 1, 2 and 3 B 1 and 2 only C 1 and 3 only D 2 and 3 only

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2025

35 Which compound is a product of the hydrolysis of CH3CO2CH2C2H5 using aqueous sodium hydroxide? A CH3CO2 –Na+ B CH3CO2H C C2H5CH2O–Na+ D C2H5CH2CO2 –Na+

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2025

37 The table shows the reagents and products of three reactions. reagents products 1 ethanoic acid + Na2CO3 CH3CO2Na + H2O + CO2 2 ethanoic acid + Mg (CH3CO2)2Mg + H2O 3 ethanoic acid + CH3OH CH3CO2CH3 + H2O Which rows are correct? A 1, 2 and 3 B 1 and 2 only C 1 and 3 only D 2 and 3 only

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2025