5.3 Planning a Grignard synthesis

1.1 Structures of the geometry of alcohol
1.2 Nomenclature

2.1 Primary alcohol
2.2 Secondary alcohol
2.3 Tertiary alcohol

4.1 By hydrolysis of alkyl halide
4.2 Acid catalysed hydration of alkenes
4.3 Oxymercuration Demercuration
4.4 Hydroboration-oxidation
4.5 Hydroxylation of alkenes
4.6 From organometallic compounds
4.6 Reduction of Esters

5.1 Reaction & Mechanism
5.2 Product of Grignard reagent
5.3 Planning a Grignard synthesis
5.4 Restriction of the use of Grignard reagents

6.1 Acidic character
6.2 Dehydration
6.3 Reaction with phosphorus trihalide or thionyl chloride
6.4. Reaction with hydrogen halide
6.5 Oxidation of Alchols

7.1 Test Distinguishing 1°, 2° and 3° Alcohols
7.2 Victor Mayor Test: ???????

8.1 Nomenclature
8.2 Physical Properties of Ethers
8.3 Preparation of Ethers

9.1 Mechanism: ???????

11.1 Reactions of Epoxides

12.1 Nomenclature of Phenols

13.1 Laboratory synthesis:
13.2 Industrial synthesis:

By using Grignard synthesis skillfully, we can synthesize almost any alcohol we want.

In planning a Grignard synthesis we must simply choose the correct Grignard reagent and the correct aldehyde, ketone, ester or epoxide. We do this by examining the alcohol we wish to prepare and by paying special attention to the groups attached to the carbon atom bearing the $—OH$ group.

Many times there may be more than one way of carrying out the synthesis. In these cases, our final choice will probably be dictated by the availability of starting compound.

Suppose we want to prepare $3-$phenyl $3-$ pentanol.

We examine its structure and we see that the groups attached to the carbon atom bearing the $–OH$ are a phenyl group and two ethyl group.

We can synthesize this compound in different ways.

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

2. We can use a ketone containing an ethyl group and a phenyl group and allow it to react with ethyl magnesium bromide.