Formulas, functional groups and the naming of organic compounds — Paper 1 · A Level Chemistry 9701

25 Compounds X, Y and Z all react with PCl5 to release hydrogen chloride, but only one of them reacts with 2,4-dinitrophenylhydrazine reagent. Which one of the following combinations could be X, Y and Z ? X Y Z CH2OH CHO CO2H A CH2OH CHO CO2H CH2OH CH2OH CHO B CH2OH CHO CO2H CH2OH CH2OH CHO C CHO CO2H CO2H CH2OH CHO CO2H D CO2H CO2H CO2H

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2005

20 In which class of compound, in its general formula, is the ratio of hydrogen atoms to carbon atoms the highest? A alcohols B aldehydes C carboxylic acids D halogenoalkanes

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2006

19 In an historically famous experiment Wöhler heated ‘inorganic’ ammonium cyanate in the absence of air. The only product of the reaction was ‘organic’ urea, CO(NH2)2. No other products were formed in the reaction. What is the formula of the cyanate ion present in ammonium cyanate? A CNO– B CNO2– C CO– D NO–

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2009

38 Which structural formulae represent 2,2-dimethylpentane? 1 (CH3)2CHCH2CH(CH3)2 2 (CH3)3CCH2CH2CH3 3 CH3CH2CH2C(CH3)3

1 marks

Answer: C

This question in 9701/11 May/June 2010

39 Which structural formulae represent 2,2-dimethylpentane? 1 (CH3)2CHCH2CH(CH3)2 2 (CH3)3CCH2CH2CH3 3 CH3CH2CH2C(CH3)3

1 marks

Answer: C

This question in 9701/12 May/June 2010

37 Which structural formulae represent 2,2-dimethylpentane? 1 (CH3)2CHCH2CH(CH3)2 2 (CH3)3CCH2CH2CH3 3 CH3CH2CH2C(CH3)3

1 marks

Answer: C

This question in 9701/13 May/June 2010

20 One of the characteristics of addition polymerisation is that the empirical formulae of the polymer and of its monomer are the same. The absorbent material in babies’ disposable nappies is made from the addition polymer shown. CH2 CH2 CH2 CH CH CH CO2H CO2H CO2H From which monomer could this addition polymer be obtained? A CH3CH(OH)CO2H B HOCH2CH2CO2H C H2C=CHCO2H D HO2CCH=CHCO2H

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2010

33 Which types of intermolecular forces can exist between adjacent urea molecules? O C H2N NH2 urea 1 hydrogen bonding 2 permanent dipole-dipole forces 3 temporary induced dipole-dipole forces

1 marks

Answer: A

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

25 Which formulae show propanone and propanal as different compounds? A empirical, molecular, structural and displayed formulae B molecular, structural and displayed formulae only C structural and displayed formulae only D displayed formulae only

1 marks

Answer: C

This question in 9701/12 May/June 2011

22 In the general formula of which class of compound, is the ratio of hydrogen atoms to carbon atoms the highest? A alcohols B aldehydes C carboxylic acids D halogenoalkanes

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2011

5 Methyl isocyanate, CH3NCO, is a toxic liquid which is used in the manufacture of some pesticides. In the methyl isocyanate molecule, the sequence of atoms is H3C — N C O. What is the approximate angle between the bonds formed by the N atom? A B C D N C O N C O N C O H3C N C O H3C H3C H3C 104° 109° 120° 180°

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2011

30 Which statement does not correctly describe the polymer PVC? A Combustion of PVC waste produces a highly acidic gas. B PVC molecules are saturated. C The empirical formula of PVC is the same as the empirical formula of its monomer. D The repeat unit of PVC is –(CHCl CHCl )–.

1 marks

Answer: D

This question in 9701/11 May/June 2012

21 Which diagram gives the skeletal formula of 2-chloropentan-3-ol? A B C D Cl Cl OH Cl Cl OH OH OH

1 marks

Answer: A

This question in 9701/12 May/June 2012

20 Carvone is found in spearmint. CH3 O C H C C H2C CH2 C C H H3C CH2 carvone How many σ and π bonds are present in this molecule? σ π A 13 3 B 22 3 C 22 6 D 25 3

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2012

20 Carvone is found in spearmint. CH3 O C H C C H2C CH2 C C H H3C CH2 carvone How many σ and π bonds are present in this molecule? σ π A 13 3 B 22 3 C 22 6 D 25 3

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2012

29 What is the skeletal formula of 2-methylpentan-1-ol? A B C D OH OH OH OH

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2012

18 In a famous experiment, Wöhler heated ‘inorganic’ ammonium cyanate in the absence of air. The only product of the reaction was ‘organic’ urea, CO(NH2)2. No other products were formed in the reaction. What is the formula of the cyanate ion present in ammonium cyanate? A CNO– B CNO2– C CO– D NO–

1 marks

Answer: A

This question in 9701/13 May/June 2013

20 Which diagram gives the skeletal formula of 2-bromopentan-4-ol? A B C D OH Br Br Br OH OH Br OH

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2013

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

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

27 Methyl methylpropenoate is the monomer used to make Perspex. Which diagram correctly shows methyl methylpropenoate? A B CH3 CH2 C CH3 CH CH CO2CH3 CO2CH3 C D CH3 CH2 CH CO2CH2CH3 C CH CO2CH3 CH3

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2014

27 Methyl methylpropenoate is the monomer used to make Perspex. Which diagram correctly shows methyl methylpropenoate? A B CH3 CH2 C CH3 CH CH CO2CH3 CO2CH3 C D CH3 CH2 CH CO2CH2CH3 C CH CO2CH3 CH3

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2014

25 Terpinen-4-ol is one of the active ingredients in tea tree oil. HO terpinen-4-ol What is the molecular formula of terpinen-4-ol? A C7H11O B C10H16O C C10H17O D C10H18O

1 marks

Answer: D

This question in 9701/12 May/June 2015

29 What is the skeletal formula of 2-methylpentan-1-ol? A B C D OH OH OH OH

1 marks

This question in 9701/12 Oct/Nov 2015

21 Synthetic resins can be made by polymerisation of a variety of monomers including prop-2-en-1-ol, CH2=CHCH2OH. Which structure represents the repeat unit in poly(prop-2-en-1-ol)? A CH2 CH2 CH2 O B CH2 CH CH2OH C CH C CH2OH D CH2 CH2 CH OH

1 marks

Answer: B

This question in 9701/12 May/June 2016

20 What is the correct name of the molecule with the skeletal formula shown? HO A 1,2,2-trimethylbutan-3-ol B 2-ethyl-2-methylbutan-2-ol C 3,3-dimethylpentan-2-ol D 4-hydroxy-3,3-dimethylpentane

1 marks

Answer: C

This question in 9701/13 May/June 2016

21 Geraniol and linalool are compounds found in some flower fragrances. CH3 CH3 HO C CH2OH C H2C C H2C C H H2C H H2C CH2 CH CH C C H3C CH3 H3C CH3 geraniol linalool Which statement is correct? A They are chain isomers of each other. B They are geometrical isomers of each other. C They are optical isomers of each other. D They are positional isomers of each other.

1 marks

Answer: D

This question in 9701/12 May/June 2017

21 What is the name of compound X? OH compound X A trans-2-hydroxyhex-3-ene B trans-2-hydroxyhexene C trans-5-hydroxyhex-3-ene D trans-5-hydroxyhexene

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2017

21 The diagram shows the skeletal formula of citric acid. O OH O O HO OH OH citric acid What is the molecular formula of citric acid? A C6H8O7 B C6H4O7 C C8H8O7 D C10H8O7

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2017

21 What is the name of compound X? OH compound X A trans-2-hydroxyhex-3-ene B trans-2-hydroxyhexene C trans-5-hydroxyhex-3-ene D trans-5-hydroxyhexene

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2017

37 Polymer Z contains the length of polymer chain shown below. This short length of chain is found many times within the chains of polymer Z, although it is not the repeat unit. – CH2 – CHCl – CH2 – What could be the name of polymer Z? 1 poly(2-chloropropene) 2 poly(chloroethene) 3 PVC

1 marks

Answer: C

This question in 9701/11 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

19 If ammonium cyanate is heated in the absence of air, the only product of the reaction is urea, CO(NH2)2. No other products are formed in the reaction. What is the formula of the cyanate ion present in ammonium cyanate? A CON2 – B CON2 2– C OCN– D OCN2–

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2018

21 Which compound has the molecular formula C6H10O? A B C D O O O OH

1 marks

Answer: A

This question in 9701/11 May/June 2019

25 The structure of coniine is shown. coniine N CH2CH2CH3 H Coniine can be synthesised by reacting ammonia with a dibromo compound, X. NH3 + C8H16Br2 → coniine + 2HBr X What is the name of compound X? A 1,1-dibromo-2-propylcyclopentane B 1,2-dibromo-2-propylcyclopentane C 1,4-dibromooctane D 1,5-dibromooctane

1 marks

Answer: D

This question in 9701/11 May/June 2019

21 The diagram shows the skeletal formula of compound Y. Y OH O O OH What is the empirical formula of Y? A CHO B CH2O2 C C2HO2 D C4H4O4

1 marks

Answer: A

This question in 9701/13 May/June 2019

37 The structure of tiglic acid is CH3CH=C(CH3)CO2H. Which statements about the properties of one molecule of this acid are correct? 1 It contains two π bonds. 2 It contains four lone pairs of electrons. 3 It has all its atoms in the same plane.

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2019

20 Which pair of compounds are functional group isomers of each other? A butan-1-ol and butanal B ethylpropanoate and pentanoic acid C hex-1-ene and hex-2-ene D propylamine and propanenitrile

1 marks

Answer: B

This question in 9701/12 Feb/March 2020

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

20 The skeletal formula of compound X is shown. O Which row is correct? observation on molecular addition of X to formula of X Fehling’s reagent A C7H14O no change B C7H14O red precipitate forms C C7H16O no change D C7H16O red precipitate forms

1 marks

Answer: A

This question in 9701/11 May/June 2020

28 The structure of compound Q is shown. compound Q O O O O How many chiral centres are present in a molecule of Q? A 4 B 5 C 6 D 7

1 marks

Answer: D

This question in 9701/11 May/June 2020

30 The skeletal formula of compound X is shown. compound X HO What is the molecular formula of compound X? A C10H18O B C10H20O C C11H22O D C11H24O Section B

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2020

21 What is the correct name for the compound shown? HO A 1,2,2-trimethylbutan-3-ol B 2-ethyl-2-methylbutan-2-ol C 3,3-dimethylpentan-2-ol D 4-hydroxy-3,3-dimethylpentane

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2020

23 Compound X contains two functional groups. compound X O CH3 C CHO Which reagent will react with only one of the functional groups? A acidified potassium dichromate(VI) B 2,4-DNPH reagent C hydrogen cyanide D NaBH4

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2020

30 The skeletal formula of compound X is shown. compound X HO What is the molecular formula of compound X? A C10H18O B C10H20O C C11H22O D C11H24O Section B

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2020

23 Limonene is a hydrocarbon found in the rind of citrus fruits. limonene What is the molecular formula of limonene? A C10H12 B C10H14 C C10H16 D C10H18

1 marks

Answer: C

This question in 9701/11 May/June 2021

33 A gaseous hydrocarbon has a density of 2.42 g dm–3 under room conditions. What could be the skeletal formula of this hydrocarbon? 1 2 3

1 marks

Answer: D

This question in 9701/11 May/June 2021

20 The formula of hydrocortisone acetate is shown. hydrocortisone acetate O CH2OCOCH3 CH3 HO OH CH3 O Which row is correct? number of C atoms number of chiral atoms in one molecule in one molecule A 22 7 B 22 8 C 23 7 D 23 8

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2021

26 Compound X contains an alcohol group and a carbonyl group. compound X OH O Which row is correct? type of type of alcohol group carbonyl group A primary aldehyde B primary ketone C tertiary aldehyde D tertiary ketone

1 marks

Answer: D

This question in 9701/13 May/June 2022

5 How many σ bonds are present in one H–C≡C–C(CH3)=CH(CH3) molecule? A 5 B 11 C 13 D 16

1 marks

Answer: C

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

24 If ammonium cyanate is heated in the absence of air, the only product of the reaction is urea, CO(NH2)2. No other products are formed in the reaction. What is the formula of the cyanate ion present in ammonium cyanate? A CON2 – B CON2 2– C OCN – D OCN2–

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2023

25 Hexamine is a crystalline solid used as a fuel in portable stoves. The diagram shows its skeletal structure. hexamine N N N N What is the empirical formula of hexamine? A CH2N B C3H6N2 C C4H8N4 D C6H12N4

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2023

28 Which row shows the correct name and classification of the halogenoalkane shown? CH3(CH2)2CBr(CH3)CH2CH3 classification of name halogenoalkane A 3-bromo-3-methylhexane secondary B 3-bromo-3-methylhexane tertiary C 3-bromo-4-methylhexane tertiary D 4-bromo-5-methylhexane secondary

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2023

24 If ammonium cyanate is heated in the absence of air, the only product of the reaction is urea, CO(NH2)2. No other products are formed in the reaction. What is the formula of the cyanate ion present in ammonium cyanate? A CON2 – B CON2 2– C OCN – D OCN2–

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2023

25 Hexamine is a crystalline solid used as a fuel in portable stoves. The diagram shows its skeletal structure. hexamine N N N N What is the empirical formula of hexamine? A CH2N B C3H6N2 C C4H8N4 D C6H12N4

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2023

27 The diagram shows the skeletal formula of citric acid. citric acid O OH O O HO OH OH What is the molecular formula of citric acid? A C6H8O7 B C6H4O7 C C8H8O7 D C10H8O7

1 marks

Answer: A

This question in 9701/11 May/June 2024

24 In the general formula of which class of compound is the ratio of hydrogen atoms to carbon atoms the highest? A alcohols B aldehydes C carboxylic acids D halogenoalkanes

1 marks

Answer: A

This question in 9701/12 May/June 2024

26 What is the correct name of the major product of the reaction of HBr with 3-ethylhex-3-ene? A 3-bromo-3-ethylhexane B 3-bromo-4-ethylhexane C 4-bromo-3-ethylhexane D 4-bromo-4-ethylhexane

1 marks

Answer: A

This question in 9701/13 May/June 2024

6 P is a compound that burns in an excess of oxygen to give carbon dioxide and water only. 2.20g of P contains 1.20g of carbon and 0.20g of hydrogen. When P is added to a solution of sodium carbonate, bubbles of gas are seen. What is P? A CH3CHO B CH3CO2H C CH3COCH2CH2OH D CH3CH2CH2CO2H

1 marks

Answer: D

This question in 9701/11 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