Answers to end-of-chapter questions

Chapter 17
1 a i propanone [1] ii propan-1-ol [1] iii ethanal [1] iv propan-2-ol [1] v butanone [1] vi propanal [1] b from part a, ii and iv are alcohols; i, iii, v and vi are carbonyl compounds [1] c from part a, iii and vi are aldehydes; i and v are ketones [1] d i start with ii to make vi; start with iv to make i [4] CH3CH2CH2OH + [O]  CH3CH2CHO + H2O [1] Cr2O72/H+(aq), warm and distil immediately[1] CH3CH(OH)CH3 + [O]  CH3COCH3 + H2O [1] Cr2O72/H+(aq), reflux [1] e i compound iii [1] ii NaBH4 [1] iii CH3CHO + 2[H] CH3CH2OH [1]  Total = 19 2 a 2,4-dinitrophenylhydrazine (2,4-DNPH) solution (Bradys reagent) [1] b orange precipitate [1] c the original aldehyde or ketone could be positively identified [1]  Total = 3 3 a i  ii  iii 
O H O

4 a NaBH4 b water c
+ C H3C

[1] [1]
O H3C O: C H OH H 3C C H H + HO H H O H

H :H

nucleophilic addition [1] dipole [1] curly arrow from lone pair on hydride ion (H) to electron-deficient carbon [1] structure of intermediate [1] curly arrow from lone pair on negative oxygen onto hydrogen (+) on water [1] curly arrow from H O bond in water onto OH (O atom in water) [1] final products [1]  Total = 9 5 a Carbon Mass of element in 100g 66.7g Hydrogen 11.1g Oxygen 22.2g

Number of 66.7 = 5.56 moles 12.0 Relative number of atoms 5.56 =4 1.39

11.1 22.2 = 1.39 = 11.1 1.0 16.0 11.1 =8 1.39 1.39 =1 1.39 [2] [1] [1]

[1]

[1]

1 mark for number of moles, 1 mark for relative number of atoms empirical formula = C4H8O b empirical formula mass = 72, so molecular formula is C4H8O

[1] [1] [1] [1] [1] Total = 7

b pentan-3-one gives no change pentanal gives a silver mirror pentanal gives pentanoic acid this is an oxidation 

AS and A Level Chemistry Cambridge University Press

Answers to end-of-chapter questions: Chapter 17

c
H 3C

O C butanone CH3 H3C CH C CH2 CH3 H3C CH2 butanal O CH2 C

O H

1 mark for each isomer

H 2methylpropanal

d test with Tollens reagent: formation of silver mirror indicates aldehyde; no silver mirror indicates ketone; add 2,4-dinitrophenylhydrazine; filter precipitate and purify by recrystallisation; find melting point of precipitate and compare with literature to find the identity  [3]

[1] [1] [1] [1] [1] Total = 12

Examiners tip
The use of 2,4-DNPH reagent and the use of Tollens reagent are needed very frequently on AS- and A-level chemistry papers. Practise these two questions regularly.

Answers to end-of-chapter questions: Chapter 17

AS and A Level Chemistry Cambridge University Press