Chapter 18.9, Problem 18.8P

Predict the products of the following reactions.

1. a. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{C }\equiv {\text{ N + CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{MgBr}$, then H₃O⁺
2. b. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{C }\equiv \text{ N+DIBAL-H}$, then H₃O⁺
3. c. benzyl bromide + sodium cyanide
4. d. product of (c) + cyclopentylmagnesium bromide, then acidic hydrolysis
5. e. product of (c)+ DIBAL-H, then hydrolysis