Answers to end-of-chapter questions

Chapter 25
1 a i ethanol [1] ethanoic acid [1]  a few drops of concentrated sulfuric acid as catalyst [1] ii C2H5OH + CH3COOH  CH3COOC2H5 + H2O [1] b i phenol [1] benzoyl chloride [1] warm reaction mixture [1] ii C6H5OH + C6H5COCl  C6H5COOC6H5 + HCl [1] Total = 8 2 a
H H C H C H C C Cl O

Examiners tip
Describing the behaviour of electrons is very important in explaining organic chemistry for example, in the definitions of electrophiles and nucleophiles and when giving the reason why ethanoyl chloride hydrolyses much faster than chloroethane. Question 2, part b iii is another example of a question that has to be answered with reference to what is happening to the electrons in the molecule.

iv

O H

O  Cl v  2,2-dichlorobutanoic acid or 2,3-dichlorobutanoic acid

[1] [1] Total = 8 [1]

 H H H b i phosphorus(V) chloride, PCl5 / phosphorus(III) chloride, PCl3 / sulfur dichloride oxide, SOCl2 ii C4H9COOH + PCl5  C4H9COCl + POCl3 + HCl or

[1] [2]

3 a tri-iodomethane b H
H H C O C H C H

 3C4H9COOH + PCl3 heat  3C4H9COCl + H3PO3  or  C4H9COOH + SOCl2  C4H9COCl + SO2 + HCl [1] iii Chlorine atom withdraws electrons from the COOH group [1]  weakening the O H bond so it is easier to lose an H+ ion. [1]

 H H H [1] c propanone [1] d i butan-1-ol, butan-2-ol, methylpropan-1-ol, methylpropan-2-ol [1] ii butan-1-ol is primary, butan-2-ol is secondary, methylpropan-1-ol is primary, methylpropan-2-ol is tertiary [1] iii only butan-2-ol [1] Total = 6

AS and A Level Chemistry Cambridge University Press

Answers to end-of-chapter questions: Chapter 25