ALCOHOL

Preparation
(1) Hydrolysis of alkyl halides This reaction is useful only with reactants that do not undergo E2 elimination readily. It is really used for the synthesis of alcohols where alkyl halides are primary in nature.

(2) Reaction of Grignard reagents with aldehydes and ketones A method that allows for alcohol preparation with formation of new carbon bonds. Primary, secondary, and tertiary alcohols can all be prepared and stepping up to two carbon atom also can takes place by the help of cyclic epoxides.

(3) Reaction of organolithium reagents with aldehydes and ketones Organolithium reagents react with aldehydes and ketones in a manner similar to that of Grignard reagents to form alcohols. Other reagents which are less reactive than alkyl lithium is dialkyl cadmium, R2Cd where active species is carbanian, and forms similar kind of product.

(4) Reaction of Grignard reagents with esters Produces tertiary alcohols in which two of the substituents on the hydroxyl- bearing carbon are derived from the Grignard reagent. If we want to stop this reaction at carbonyl compound we must use less reactive reagent like dialkyl cadmium R2Cd. Remember the alkyl group in ester goes out finally as alcohol.

Chemical properties of alcohol (i) Acidic nature of alcohol Even alcohol are neutral to litmus and do not reacts with alkali like NaOH but contain active hydrogen atom so reacts with Na or K metal.

(ii)

Reaction

with

Thionyl

chloride

and

phosphorus

Halides

Dehydration of alcohols Alcohols when are reacts with any dehydrating reagent to form alkenes with removal of water. Intermediate carbocation formation takes place where rearrangement occurs by alkyl shift, hydride shift and ring expansion.

In smaller ring always ring expansion takes place due to molecular strain and they

tends

to

convert

to

high

stability

with

large

ring.

In Dehydration of alcohols

(vi) Alcoholation of alkyne When alcohols reacts with alkyne in the presence of BF3 and HgO, according to markonikoffs rule they forms ethers.

d) Catalytic dehydrogenation: It involves the passing of vapours of alcohol over reduced copper at 300C and the product thus formed is identified. (i) Primary alcohols give aldehydes (dehydrogenation). (ii) Secondary alcohols give ketones (dehydrogenation). (iii) Tertiary alcohols form olefins (alkenes). This is dehydration