Advices For Studying Organic Chemistry

+

NH 4 Cl

CH 3 CH 2 CH 2 CH 2 MgBr CH 3 CH 2 CH 2 CH 2

CH 3 CH 2 CH 2 CH 2

2-Methyl-2-hexanol (92%)

H 3 C

C

H 3 C

O

Acetone

Et 2 O

Butylmagnesium bromide

C OMgX

CH 3

CH 3

C OH

CH 3

CH 3

H 2 O

Reaction with an ester

+

H 3 C

C

C 2 H 5 O

O C OMgBr

CH 3

OCH 2 CH 3

CH 3 CH 2

CH 3 CH 2

CH 3 CH (^2) CH 2 CH 3
CH 3 CH 2 MgBr
CH 3 CH 2
CH 2 CH 3
CH 3 CH 2 MgBr
C OH
CH 3
Ethyl acetate
H 3 C
C O C OMgX
CH 3
Ethylmagnesium
bromide
−C 2 H 5 OMgBr
3-Methyl-3-pentanol
(67%)
NH 4 Cl
H 2 O

12.8A PLANNING A GRIGNARD SYNTHESIS

CH 3 CH 2 C CH 2 CH 3

C 6 H 5

3-Phenyl-3-pentanol

OH

1. We can use a ketone with two ethyl groups (3-pentanone) and allow it to react
   with phenylmagnesium bromide:
   Analysis

CH 3 CH 2 C CH 2 CH 3 CH 3 CH 2 CH 2 CH 3

C 6 H 5

C + C 6 H 5 MgBr

OH O