Alcohols — Paper 1 · A Level Chemistry 9701

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

38 Which compounds when heated under reflux with an excess of hot acidified potassium dichromate(VI), give a product with a chiral centre? CH3 1 CH3CH2CCH2OH H CH3 2 CH3CH2CCH2OH CO2H CH3 3 CH3COCCH(OH)CH3 CO2CH3

1 marks

Answer: D

This question in 9701/12 May/June 2011

29 Geraniol is a constituent of some perfumes. OH geraniol Which statement about geraniol is not correct? A Geraniol causes hot acidified potassium dichromate(VI) to change colour from orange to green. B Geraniol decolourises bromine water. C There are three methyl groups and three methylene (CH2) groups in geraniol. D There are two pairs of cis-trans isomers of geraniol.

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2011

29 Compound X, molecular formula C4H8, undergoes the following reactions. Br2 aq.NaOH / heat C4H8 C4H8Br2 C4H10O2 X Y Z H2 / Ni C4H8 methylpropane X What is the formula of compound Z? A CH3CH2CH(OH)CH2OH B CH3CH(OH)CH(OH)CH3 C CH3CH(CH2OH)CH2OH D (CH3)2C(OH)CH2OH

1 marks

This question in 9701/12 Oct/Nov 2011

30 How many of the isomeric alcohols with the formula C4H9OH will produce an alkene that has cis and trans isomers, on treatment with conc. H2SO4? A 1 B 2 C 3 D 4

1 marks

This question in 9701/12 Oct/Nov 2011

38 An organic compound Y, molecular formula C6H14O, may be oxidised to compound Z, molecular formula C6H12O2. What could be the structural formula of Y? 1 CH3CH2CH(CH2OH)CH2CH3 2 (CH3)3CCH2CH2OH 3 CH3CH2CH(CH3)CH2CH2OH

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2013

39 Which reactions can be used to make an alcohol in the laboratory? 1 hydrolysis of a bromoalkane with NaOH(aq) 2 reduction of a ketone with NaBH4 3 reduction of an aldehyde with NaBH4

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2013

27 Which reagent will give a different observation with compounds W and X? CH2OH CH3 OH W X A hot SOCl 2 B hot acidified K2Cr2O7 C NaOH(aq) D warm Fehling’s reagent

1 marks

Answer: B

This question in 9701/11 May/June 2015

39 Which compounds will react with HBr to give the compound R? Br R 1 2 3 OH

1 marks

Answer: A

This question in 9701/11 May/June 2015

25 Compound X has been investigated for use as an artificial sweetener. OH Cl O O OH OH O Cl OH OH X The two C–Cl bonds can be hydrolysed by hot NaOH(aq). The C-O-C bonds cannot be hydrolysed by hot NaOH(aq). What are the numbers of specified types of –OH groups before and after hydrolysing the two C–Cl bonds? before after hydrolysis hydrolysis secondary primary secondary tertiary A 0 1 2 4 B 0 2 1 4 C 4 1 5 1 D 4 2 4 1

1 marks

This question in 9701/12 Oct/Nov 2015

25 Malic acid is found in apples. OH H C CH2CO2H CO2H malic acid Which reagent will react with only one of the – OH groups in the malic acid molecule? A ethanoic acid in the presence of concentrated sulfuric acid B sodium C sodium hydrogen carbonate D sodium hydroxide

1 marks

Answer: A

This question in 9701/12 May/June 2016

26 Which organic compound would not give either a yellow precipitate when treated with alkaline aqueous iodine or an orange precipitate when treated with 2,4-dinitrophenylhydrazine reagent? A propanal B propan-1-ol C propan-2-ol D propanone

1 marks

Answer: B

This question in 9701/12 May/June 2016

28 How many of the following compounds produce a carboxylic acid on heating under reflux with an excess of hot acidified K2Cr2O7? CH3CH2CHO CH3COCH3 CH3CH2CH2OH CH3CH(OH)CH3 A 1 B 2 C 3 D 4

1 marks

Answer: B

This question in 9701/12 May/June 2016

40 Which syntheses will be successful? 1 CH3CH2CH3 from CH3CH=CH2 + LiAl H4 2 CH3CH(OH)CH3 from CH3COCH3 + NaBH4 3 CH3CH2CH2OH from CH3CH2CHO + NaBH4

1 marks

Answer: C

This question in 9701/12 May/June 2016

30 Which compound, when hydrolysed, gives propanoic acid and propan-2-ol? A CH3CH2CO2CH2CH(CH3)CH3 B (CH3)2CHCO2CH2CH3 C CH3CH2CO2CH(CH3)CH3 D CH3CH2CH2CO2CH(CH3)CH3 Section B

1 marks

Answer: C

This question in 9701/12 May/June 2017

27 Which compound will react with acidified potassium dichromate(VI) and with alkaline aqueous iodine? A CH3COCH2CH3 B CH3CH(OH)CH2CH3 C CH3CH2CH2CHO D CH3CH2CH2CH2OH

1 marks

Answer: B

This question in 9701/13 May/June 2017

39 The compounds below are used to make perfumes. Which compounds will produce a yellow precipitate with alkaline aqueous iodine? 1 2 3 OH OH HO O OH OH

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2017

39 The compounds below are used to make perfumes. Which compounds will produce a yellow precipitate with alkaline aqueous iodine? 1 2 3 OH OH HO O OH OH

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2017

29 Alcohols, aldehydes and nitriles can each be converted into carboxylic acids. Which descriptions of their conversions into carboxylic acids are correct? alcohols aldehydes nitriles A hydrolysis hydrolysis hydrolysis B hydrolysis hydrolysis oxidation C oxidation oxidation hydrolysis D oxidation oxidation oxidation

1 marks

Answer: C

This question in 9701/12 Feb/March 2018

39 Which statements about 2-methylbutan-1-ol are correct? 1 It can give HCl (g) on reaction with PCl 5. 2 It can be oxidised to give an aldehyde. 3 It displays optical isomerism.

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2018

40 The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass. O cis-hex-3-enal Which reagents will react with cis-hex-3-enal? 1 sodium 2 sodium borohydride 3 Fehling’s reagent

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2018

39 An unknown organic compound Z reacts with sodium to give a combustible gas as one product. Z does not give a yellow precipitate with alkaline aqueous iodine. What is a possible identity of Z? 1 ethanoic acid 2 pentan-3-ol 3 propan-1-ol

1 marks

Answer: A

This question in 9701/13 May/June 2019

38 Which compounds, on heating with an excess of concentrated sulfuric acid, produce only one product with molecular formula C7H10? 1 2 3 OH OH OH OH OH OH

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2019

38 Which compounds, on heating with an excess of concentrated sulfuric acid, produce only one product with molecular formula C7H10? 1 2 3 OH OH OH OH OH OH

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2019

37 Which reagents could be used, under suitable conditions, to oxidise CH3CH2CH2OH to CH3CH2CHO? 1 acidified potassium manganate(VII) 2 acidified potassium dichromate(VI) 3 Tollens’ reagent

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2020

34 Pentaerythritol is used as an intermediate in the manufacture of paint. pentaerythritol HOCH2 CH2OH C HOCH2 CH2OH Which statement is correct? A Pentaerythritol can be dehydrated by concentrated sulfuric acid to form an alkene. B The empirical formula and molecular formula of pentaerythritol are different. C Pentaerythritol does not react with acidified potassium manganate(VII). D One mole of pentaerythritol gives two moles of hydrogen gas on reaction with an excess of sodium.

1 marks

Answer: D

This question in 9701/13 May/June 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 9701/11 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

32 Tartaric acid, HOOCCH(OH)CH(OH)COOH, is found in many plants. A sample of tartaric acid reacts with an excess of LiAlH4 to form the organic product J. What happens when NaOH(aq) is added to separate samples of tartaric acid and J? A Both tartaric acid and J react. B Only tartaric acid reacts. C Only J reacts. D Neither tartaric acid nor J react.

1 marks

Answer: B

This question in 9701/12 Feb/March 2023

33 Citric acid can be converted into tricarballylic acid in two stages. An intermediate, Q, is formed. CH2 COOH CH2 COOH stage 1 stage 2 HO C COOH Q CH COOH CH2 COOH CH2 COOH citric acid tricarballylic acid Which reagents are needed for each stage? stage 1 stage 2 A concentrated H2SO4 H2(g) and Ni B concentrated H2SO4 LiAlH4 C LiAlH4 H2SO4(aq) D NaOH(aq) H2(g) and Ni

1 marks

Answer: A

This question in 9701/12 Feb/March 2023

35 Two isomeric alcohols, W and X, have molecular formula C4H9OH. W is oxidised to carbonyl compound Y which gives a red precipitate with Fehling’s solution. X is oxidised to carbonyl compound Z which does not give a red precipitate with Fehling’s solution. Which of W and X gives a yellow precipitate with alkaline I2(aq)? A insufficient data is given to answer this question B W only C X only D neither W nor X

1 marks

Answer: C

This question in 9701/12 Feb/March 2023

38 The infrared spectrum of an organic compound is shown. 100 transmittance / % 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 bond functional groups containing the bond characteristic infrared absorption range (in wavenumbers) / cm–1 C–O hydroxy, ester 1040–1300 C=C aromatic compound, alkene 1500–1680 C=O amide 1640–1690 carbonyl, carboxyl 1670–1740 ester 1710–1750 C≡N nitrile 2200–2250 C–H alkane 2850–3100 N–H amine, amide 3300–3500 O–H carboxyl 2500–3000 hydroxy 3200–3650 Which compound could give this spectrum? A CH3CH2CO2H B CH3CH(OH)CH3 C CH3COCH3 D CH3COCH2OH

1 marks

Answer: C

This question in 9701/12 Feb/March 2023

33 Alcohol X gives a yellow precipitate with alkaline I2(aq). What is the structure of X? A B C D OH CH2OH OH OH

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2023

36 Which compound will produce a yellow-orange precipitate when added to 2,4-dinitrophenylhydrazine? A B C D O O O OH O Ethanal, CH3CHO, undergoes an addition reaction with HCN in the presence of CN– ions.

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2023

35 Heating compound X, C7H,,0,, under reflux with an excess of acidified potassium dichromate(VI) produces compound Y. Compound Y produces hydrogen gas with sodium metal and forms orange crystals with 2,4-DNPH reagent. What could X be? A B Cc D CH,OH OH CH, OH (CH,),C(OH)CH,CH,CH,CHO CH, CH,OH OH OH

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2023

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

31 The compounds shown are all produced by plants. Each compound is warmed with acidified K2Cr2O7. Which compound will give a different observation to the other three? OH A OH B C D OH OH

1 marks

Answer: D

This question in 9701/13 May/June 2025

32 Structural and stereoisomerism should be considered when answering this question. How many alcohols with the molecular formula C5H12O give a yellow precipitate with alkaline I2(aq)? A 2 B 3 C 4 D 5

1 marks

Answer: C

This question in 9701/13 May/June 2025

38 Seven aldehydes and ketones ● contain only one oxygen atom per molecule ● have four or fewer carbon atoms in their structures. Alkaline I2(aq) is added to each of these carbonyl compounds separately. How many of these carbonyl compounds produce a yellow precipitate with alkaline I2(aq)? A 1 B 2 C 3 D 4

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2025

39 Some properties of compound X are listed. ● 1.0mol X reacts with exactly 8.5mol oxygen when completely combusted. ● X does not react when heated with acidified KMnO4. What are the possible identities of X? OH 1 2 HO 3 4 OH O A 1 and 3 B 2 and 4 C 3 only D 4 only

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2025

39 Some properties of compound X are listed. ● 1.0mol X reacts with exactly 8.5mol oxygen when completely combusted. ● X does not react when heated with acidified KMnO4. What are the possible identities of X? OH 1 2 HO 3 4 OH O A 1 and 3 B 2 and 4 C 3 only D 4 only

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2025