Answers to end-of-chapter questions

Chapter 15
1 a A = aqueous sodium hydroxide (solution) B = ethanolic sodium hydroxide b reaction is faster with 1-iodobutane as C I bond is weaker than C Br bond so is broken more easily c nucleophilic substitution d +
C Br C OH + Br

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

e i 2-methylpropan-2-ol [1] ii With 2-bromo-2-methylpropane the C Br breaks to form a carbocation which is then attacked by the hydroxide ion; [1]  whereas in 1-bromobutane the C Br starts breaking as the new C OH bond is forming. [1] f elimination [1] g but-2-ene [1] Total = 13 2 a
Cl Br C F

OH curly arrow from lone pair on OH curly arrow from C Br bond to bromine  products

[1] [1] [1]

Examiners tip
Make sure that one curly arrow in this mechanism starts from a lone pair or negative charge on the hydroxide ion and points to the electron-deficient carbon atom in the alcohol and that the other starts on the C Br bond and points to the Br atom.

F  b 1-fluoro-2-trifluoroethane c depletion of the ozone layer

[1] [1] [1] Total = 3

AS and A Level Chemistry Cambridge University Press

Answers to end-of-chapter questions: Chapter 15