Chapter 15, Problem 32P

Give structures (including stereochemistry where appropriate) for compounds A–G:

(a)

(Hint: The ${}^{1}H$ NMR spectrum of compound C consists of a multiplet at $\delta$ 7.20 (5H) and a singlet at $\delta$ 2.0 (3H).)

(b) $\underset{(2)N{H}_{4}Cl(Section7.15B)}{\overset{(1)Li,EtN{H}_2}{\to }}E\left(C_9{H}_{10}\right)$

(c) $D\underset{2\text{-}5°C}{\overset{B{r}_2}{\to }}F+enantiomer\left(majorproducts\right)$

(d) $E\underset{2\text{-}5°}{\overset{Br{2}_{}}{\to }}G+enantiomer\left(majorproducts\right)$