Answers to end-of-chapter questions

Chapter 16
1 a pentan-2-ol i C5H11OH or C5H12O ii CH3CH2CH2CHOHCH3 iii H
H H C H H C H H C H OH O C H H C H H

structural isomers d 2-methylbutan-2-ol  [1] [1] 2 a H2C CH2 + H2O CH3CH2OH H3PO4 b CH3CH2OH + 3O2 2CO2 + 3H2O [1]

[1] [1] Total = 19 [1] [1]

 iv

[1 mark for the products; 1 mark for balancing] [2] c CH3CH2CHOHCH3  CH3CH2CH CH2 + H2O [1] CH3CH2CHOHCH3 H3C CH3 C H C H H C H C CH3

 [1] [1] [1] [1]

+ H2O [1]

 v secondary butan-1-ol i C4H9OH or C4H10O ii CH3CH2CH2CH2OH iii H

H H C H C H C O C H

CH3CH2CHOHCH3
H3C

+ H2O [1]

 H H H H iv OH  v primary 2-methylpropan-2-ol i C4H9OH or C4H10O ii CH3COH(CH3)2 iii H

H H H C H C C O H H H C H H

[1] [1] [1] [1] [1]

d CH3COOH + CH3CH2OH  CH3COOCH2CH3 + H2O [1] concentrated sulfuric(VI) acid [1] esterification [1] ethyl ethanoate (and water) [1]  Total = 11 3 a K2Cr2O7 [1] b i displayed formula with CHO (aldehyde group) [1] displayed formula with COOH group [1] ii gives aldehyde after mild heat and distilling immediately; [1] gives carboxylic acid after refluxing with excess oxidising agent [1] iii aldehydes [1] carboxylic acids [1] iv e.g. CH3CH2OH + [O]  CH3CHO + H2O [1] e.g. CH3CH2OH + 2[O]  CH3COOH + H2O [1] c i displayed formula with C O group (ketone) [2] ii ketones [1] iii e.g. CH3CHOHCH3 + [O]  CH3COCH3 + H2O [1] d no H atom on C atom that attaches to the OH functional group [1]  Total = 14

 iv

[1]

OH  v tertiary b CnH2n+1OH c Examiners tip

[1] [1] [1]

butan-1-ol and 2-methylpropan-2-ol

This is easiest to do if you look at the molecular formula line.

[1]
Answers to end-of-chapter questions: Chapter 16

AS and A Level Chemistry Cambridge University Press