Answers to end-of-chapter questions

Chapter 26
Examiners tip
There are some genuinely demanding areas of A-level chemistry, but everyone can learn the reagents and conditions needed for organic reactions. Questions 2b, 3a, 3b and 4a all involve this sort of straightforward recall, and there will be questions of this sort on your A-level exam. Make sure you learn all of this material thoroughly!

N N OH

arene rings and phenol OH [1] N N  [1] c C6H5N2+Cl + C6H5OH + NaOH C6H5N2C6H4OH + NaCl + H2O [1] d dye [1] Total = 6 [1] [1]
OH H2N O H C CH3 O [1 mark for each structure] [2] H C H3C [1 mark for each structure] [2]

1 a
H

H C

H C N

H N H

H H phenylamine [1 mark for each structure] [2]

5 a i glycine is aminoethanoic acid (2-aminoethanoic acid)  alanine is 2-aminopropanoic acid ii

OH H2N

H H ethylamine

b e.g. C2H5NH2 + HCl c lone pair on nitrogen

[1] C2H5NH3+Cl [1] [1] Total = 5

b i
HOOC

2 a reduction [1] b tin [1] concentrated HCl(aq) [1] c C6H5NO2 + 6[H] [1] C6H5NH2 + 2H2O [1] Total = 5 3 a sodium nitrite/sodium nitrate(III)/NaNO2 [1] dilute HCl [1] b temperature below 10C [1] c + N N Cl C6H5 group [1] N N [1] + charge and Cl ion included [1] d C6H5NH2 + NaNO2 + 2HCl [1] C6H5N2+Cl + NaCl + 2H2O [1] Total = 8 4 a temperature below 10C alkali/NaOH present [1] [1]

NH2

H2N

COOH

ii It does not have a chiral carbon (a carbon with four different groups/atoms attached), so no optical isomers [1]  and it does not have a C C double bond, so no geometrical (cis/trans) isomers. [1] Total = 8 6 a They can act as both an acid and as a base / they can act as proton acceptors and proton donors. [1] b The NH2 group has a lone pair of electrons [1] and therefore can accept a proton, i.e. act as a base. [1] The COOH group can ionise/dissociate to give COO + H+ [1] and therefore can act as an acid by donating a proton. [1] c i Glycine forms the zwitterion + H3NCH2COO, i.e. it has two ions present. [1]

AS and A Level Chemistry Cambridge University Press

Answers to end-of-chapter questions: Chapter 26

 ii They exist as ionic solids with higher than expected melting/decomposition points  because of the electrostatic attraction between oppositely charged ions on neighbouring zwitterions.  They are soluble in water  because of the interactions between the charged groups and polar water molecules. d O O
H2N CH2 C NH CH CH3 O H2N CH H3C C NH CH2 C OH C OH O

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

7 a i
H2N

CH3 O C H C OH H 2N H3 C

H C C H H H 2N C H C OH O

O C C2H5 OH

ii the top right one in the diagram above b i CO NH / amide/peptide bond/link ii Hydrolysis means splitting of a bond / breaking down a compound using water. O H O Total = 14
N H C OH NH2 + HO C

[1 mark for each structure] [3]

[1] [1] [1]

[2 marks for each structure] [4]

[1 mark for showing which bond breaks, 1 mark for products] [2]

Total = 8

Answers to end-of-chapter questions: Chapter 26

AS and A Level Chemistry Cambridge University Press