Show how you would synthesize the following alcohol from compounds containing no more than

five carbon atoms.

CH3
4 carbon
C OH with OH group

CH2CH3

5 carbons break the C-C bond here

from

MgBr
CH3 CH3

+ +C OH = C O
or
CH2CH3 CH2CH3
Li
Electrophile

Carbon Nucleophile

Synthesis
CH3
- +
MgBr CH3 C OMgBr
+ C O CH2CH3

CH2CH3

CH3
H 3O+
C OH

CH2CH3