SELECT * FROM question_mgmt as q WHERE id=1977 AND status=1 SELECT id,question_no,question,chapter FROM question_mgmt as q WHERE courseId=3 AND subId=9 AND chapterId=65 and ex_no='2' AND status=1 ORDER BY CAST(question_no AS UNSIGNED)

Question:

Predict all the alkenes that would be formed by dehydrohalogenation of the following halides with sodium ethoxide in ethanol and identify the major alkene:

(i) 1-Bromo-1-methylcyclohexane

(ii) 2-Chloro-2-methylbutane

(iii) 2,2,3-Trimethyl-3-bromopentane.

Answer:

 

Saytzeff's rule implies that in dehydrohalogenation reactions, the alkene having a greater number of alkyl groups attached to a doubly bonded carbon atoms is preferably produced. Therefore, alkene (I) i.e., 2-methylbut-2-ene is the major product in this reaction.

(iii)

2,2,3-Trimethyl-3-bromopentane

In the given compound, there are two different sets of equivalent β-hydrogen atoms labelled as a and b. Thus, dehydrohalogenation of the compound yields two alkenes.

 

According to Saytzeff's rule, in dehydrohalogenation reactions, the alkene having a greater number of alkyl groups attached to the doubly bonded carbon atom is preferably formed. Hence, alkene (I) i.e., 3,4,4-trimethylpent-2-ene is the major product in this reaction.


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