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Chapter 2: Problem 100

Reaction of trans-2-phenyl-1-bromocyclohexane with hot alcoholic \(\mathrm{NaOH}\) gives (a) 3 -phenylcyclohexene (b) 1 -phenylcyclohexene (c) 2 -bromophenyl cyclohexane (d) 2 -phenyl cyclohexanol

Short Answer

Expert verified
Answer: The product of this reaction is (a) 3-phenylcyclohexene.

Step by step solution

01

Identify the reactants

We are given the reactants as trans-2-phenyl-1-bromocyclohexane and hot alcoholic NaOH.
02

Determine the reaction mechanism

As we have an alkyl halide (bromine) and alcoholic NaOH reacting, this indicates that we have a nucleophilic substitution reaction or an elimination reaction taking place. Considering the conditions are given as hot alcoholic NaOH, an E2 elimination reaction is favored, as it is known that heat favors the formation of alkenes from alkyl halides.
03

Visualize the elimination taking place

In the E2 elimination reaction, a hydrogen from the beta-carbon is removed along with the halogen (bromine), resulting in the formation of a double bond between the alpha and beta carbon atoms. So, the bromine (Br) will be removed from the 1st carbon, and a hydrogen will be removed from the 3rd carbon.
04

Determine the possible products

Since bromine and hydrogen are eliminated from the 1st and 3rd carbon, respectively, a double bond is formed between them. Thus, the product is 3 -phenylcyclohexene.
05

Match the product with the given options

The formed product, 3 -phenylcyclohexene, corresponds to option (a) in the given exercise. So, the correct answer is (a) 3 -phenylcyclohexene.

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Most popular questions from this chapter

Alkynes are less reactive than alkenes towards electrophilic reagents. But the alkyne chemistry is useful for organic synthesis, in the form of hydration of the triple bond, formation of metalacetylides, selective reduction of alkynes and few other related reactions.

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

The number of structural and stereoisomers of a bromo compound \(\mathrm{C}_{5} \mathrm{H}_{9} \mathrm{Br}\) formed by the addition of \(\mathrm{HBr}\) to pent- 2 yne are respectively (a) 4 and 2 (b) 1 and 2 (c) 2 and 4 (d) 2 and 1

Choose the correct statement with regard to 3 -methyl but- 1 -ene (a) A tertiary alcohol is formed by hydration in the presence of an acid. (b) a primary alcohol is formed by oxymercuration reaction. (c) An optically active secondary alcohol is formed by hydroboration- oxidation. (d) The alkene is less reactive than ethene towards hydration under acid catalyzed conditions.

An alkene on mild oxidation with dil. aqueous \(\mathrm{KMnO}_{4}\) gave a product which on further treatment with \(\mathrm{HIO}_{4}\) gave hexane- 2,5 -dione. The alkene is (a) \(\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\) (b) \(\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}=\mathrm{CH}_{2}\) (c) Cyclohexane (d) 1, 2 dimethyl cyclobutene
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