Preparation of Alcohols (iii)
from Haloalkanes, Aldehydes and Ketones
From haloalkanes
Haloalkanes are heated with aqueous sodium or potassium hydroxide to form alcohols.
Identify ?A and ?B
From aldehydes and ketones
By reduction
Aldehydes and ketones are reduced to corresponding alcohols in a number of ways like :
- Addition of H2 in the presence of catalyst like platinum, nickel.
- By complex metal hydrides such as Lithium aluminium hydride (LiAlH4) or sodium boro hydride (NaBH4)
By addition of Grignard reagents
Grignard reagents (R−MgX) are polar in nature where carbon is electronegative and Mg is electropositive. Due to the polar nature of Grignard reagents, they react with aldehydes and ketones to form addition products which upon decomposition gives alcohols with water or dil. H2SO4.
Important points regarding this reaction
- When formaldehyde (HCHO) is used in the above reaction, primary alcohol is obtained.
- When aldehydes other than formaldehydes are used, secondary alcohols are obtained.
- When ketones are used, tertiary alcohols are obtained.
Identify ?A and ?B
Questions
Question : Write structures of the products of the following compounds when reduced with NaBH4.
Answer :
- The −CHO group is reduced to CH2OH. The reaction is given below:
- NaBH4, being a weak reducing agent, reduces aldehydes to alcohols, but fails to reduce ester.