Name ____ _

9. (21 points) Provide a mechanism (curved arrows) for each reaction shown below. Be sure to show any intermediates.

(b) ~

_( .7 -Jj : Br; f..r r1

\Y: (3(, C-f'roWJ ~ ...

G // M-0

HI

EtOH

CH3

l~QH H3C

....._ H O~t ._ /"-.._ ......,, 'le ...._ + H3oG er()

H Br

(racemic)

---

Name _____ _

10. (20 points) Devise a synthetic route from the indicated starting material to the indicated target. The route should be as short and as selective as possible. You may use any other organic molecules or inorganic reagents in your synthetic plan. Show the expected product after each step in each synthetic route. (Do not provide mechanistic information.)

(?~ Starting material = . r-\';I ~ Nf3c tt l)/,irt~ 0Y~ 'l2/

Brrr0 <--,-/~ ~~ LJ

Target =

0

H~

/

I

I

----7 ~ /lz_oz, /ifo..D/J

Al-z_,O

oH

~_) Br