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How will you decide whether Clemmensen, Wolff-Kishner, or Raney Ni desulphurisation is the most efficacious for reducing a carbonyl compound?

Text Solution

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a. i. Unhindered keto group is converted to cyclic ketal and then followed by reduction with by reduction with Raney Ni.

ii. A ldehyde is more reactive than the keto group and is converted to cyclic thio acetal and the reduction is effected with Raney Ni.

b.
group together with other functional groups that react with strong base must be reduced by Clemmensen reduction, provided they are stable in acid. If they are sensitive to acid and stable in base W.K. method should be used . Raney Ni desulphurisation occurs under neutral conditions, but it cannot be used with reactions with good leaving groups (such as `I^(ɵ)`) because (-SH) group is an excellent nucleophilic group.
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Read the passage given below and answer the following questions: Reductive alkylation is the term applied to the process of introducing alkyl groups into ammonia or a primary or secondary amine by means of an aldehyde or ketone in the presence of a reducing agent. The present discussion is limited to those reductive alkylations in which the reducing agent is hydrogen and a catalyst or "nascent" hydrogen, usually from a metalacid combination, most of these reductive alkylations have been carried out with hydrogen and a catalyst. The principal variation excluded is that in which the reducing agent is formic acid or one of its derivatives, this modification is known as the Leuckart reaction. The process of reductive alkylation of ammonia consists in the addition of ammonia to a carbonyl compound and reduction of the addition compound or its dehydration product. The reaction usually is carried out in ethanol solution when the reduction is to be effected catalytically Since the primary amine is formed in the presence of the aldehyde it may react in the same way as ammonia, yielding an addition compound, a Schiff's base (RCH= NCH_(2)R) and finally, a secondary amine. Similarly, the primary amine may react with the imine, forming an addition product which also is reduced to a secondary amine Finally, the secondary amine may react with either the aldehyde or the imine to give products which are reduced to tertiary amines. Similar reactions may occur when the carbonyl compound employed is a ketone. (source: Emerson, W. S. (2011). The Preparation of Amines by Reductive Alkylation. Organic Reactions, 174–255. doi:10.1002/0471264180.or004.03 ) Reductive alkylation of ammonia by means of an aldehyde in presence of hydrogen as reducing agents results in formation of:

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