Textbook: Loudon 5th Ed. (2009)

Chapter 17: Allylic and Benzylic Reactivity

Practice Problems (No matching mendel sets were found.)

Individual Problems

Problem # 580

Draw all resonance forms for each species.

For the anion and cation species, used curved arrows. For the radical species, use hooks.

Problem # 581

Draw all products for the two reactions below.

The allylic alkene gives two products- the 1,2 product, and the 1,4 product. 

However, the benzylic alkene only gives the one product (analogous to the 1,2 product), instead of multiple products (like the 1,4 product, 1,6 product, and 1,8 product). Why is this the case?

Problem # 1281

Allylic and benzylic halides tend to undergo both SN1 and SN2 substitution reactions at a faster rate than their alkyl counterparts.

For example, both allyl chloride and benzyl chloride undergo SN2 reaction at a faster rate than propyl chloride. 

The same holds true for SN1 reactions: a 2° allyl or benzyl halide undergoes SN1 reaction faster than a 2° alkyl halide. Explain.