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Chapter 2: Problem 60

Which of the following is not a \(\beta\) elimination? (a) dehydration of alcohols (b) dehydrohalogenation of alkyl halides (c) dehalogenation of vicinal dibromides (d) dehydrohalogenation of chloroform

Short Answer

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(a) Dehydration of alcohols (b) Dehydrohalogenation of alkyl halides (c) Dehalogenation of vicinal dibromides (d) Dehydrohalogenation of chloroform Answer: (d) Dehydrohalogenation of chloroform does not involve a β elimination reaction.

Step by step solution

01

(a) Dehydration of alcohols

Dehydration of alcohols involves the removal of a water molecule (H\(_2\)O) from the alcohol molecule. This reaction usually occurs under acidic conditions and is a \(\beta\) elimination reaction because a hydrogen atom on the \(\beta\) carbon is removed along with the hydroxyl group on the \(\alpha\) carbon.
02

(b) Dehydrohalogenation of alkyl halides

Dehydrohalogenation of alkyl halides involves the removal of a hydrogen atom and a halogen atom (such as Cl, Br, or I) from adjacent carbon atoms (the \(\alpha\) and \(\beta\) carbons) in the alkyl halide molecule. This reaction is also a \(\beta\) elimination process because it eliminates a hydrogen atom from the \(\beta\) carbon and a halogen atom from the \(\alpha\) carbon.
03

(c) Dehalogenation of vicinal dibromides

Dehalogenation of vicinal dibromides involves the removal of two halogen atoms (in this case, bromine) from two adjacent carbon atoms (the \(\alpha\) and \(\beta\) carbons) in the dibromide molecule. As the two halogen atoms are removed from the adjacent carbons, a \(\pi\) bond is formed between them. This reaction falls under the \(\beta\) elimination because it involves the removal of groups from adjacent carbons, although in this case, both groups are halogens.
04

(d) Dehydrohalogenation of chloroform

Chloroform (CHCl\(_3\)) is a molecule with three chlorine atoms and one hydrogen atom bonded to a central carbon atom. Dehydrohalogenation of chloroform involves removing a hydrogen atom and a chlorine atom from the molecule, which results in the formation of a dichlorocarbene (CCl\(_2\)). This reaction does not involve the elimination of groups from adjacent carbon atoms, as chloroform only has one carbon atom. Hence, this reaction does not fit into the category of \(\beta\) elimination. Based on the analysis of each option, we can conclude that:
05

Answer

Option (d) Dehydrohalogenation of chloroform is not a \(\beta\) elimination reaction.

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