Advices For Studying Organic Chemistry

Synthesis

C 6 H 5 MgBr

Phenylmagnesium
bromide

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

3-Pentanone

1. Et 2 O


2. NH 4 Cl C

C 6 H 5

H 2 O

3-Phenyl-3-pentanol

O OH

2. We can use a ketone containing an ethyl groups and a phenyl group (ethyl phenyl
   ketone) and allow it to react with ethylmagnesium bromide:
   Analysis

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

C 6 H 5

C

C 6 H 5

+

OH O

Synthesis

CH 3 CH 2 MgBr

CH 3 CH 2

+

C 6 H 5

C

Ethylmagnesium

bromide

Ethyl phenyl

O

ketone

1. Et 2 O


2. NH 4 Cl
   H 2 O

C

C 6 H 5

3-Phenyl-3-pentanol

CH 3 CH 2 CH 2 CH 3

OH

3. We can use an ester of benzoic acid and allow it to react with two molar
   equivalents of ethylmagnesium bromide:
   Analysis

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

C 6 H 5

+ 2

C 6 H 5 OCH 3

C

OH

O

Synthesis

1. Et 2 O


2. NH 4 Cl
   H 2 O

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

C 6 H 5

3-Phenyl-3-pentanol

2 +

Ethylmagnesium

bromide

Methyl benzoate

C 6 H 5 OCH 3

C

OH

O