Chapter 10: Conjugation in Alkadienes and Allylic System

Nucleophilic Substitution Reactions of Allyl Halides

• Allyl chlorides, bromides and iodides are good substrates for nucleophilic substitution reactions.
• A variety of nucleophiles can be used to generate a range of new functional groups.
• The process can be complicated by the allylic rearrangement where the nucleophile can attack either of the electron deficient sites.

QUESTION

• Can you account for why the 3^o alcohol is the major product ? ANSWER
• What does the fact that both the reactions shown give the same product mixture suggest ? ANSWER

• Substitution reactions of alkyl halides
• Substitution reactions of benzylic halides (see Chapter 11)

© Dr. Ian Hunt, Department of Chemistry