Question Details

Options

A

B

C

D

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Correct Answer :

Option C

B is 4-bromostyrene, C is 1-bromo-4-(1-bromoethyl)benzene, and A and C are position isomers.

Solution :

Correct Option: Option 3 (which shows B as 4-bromostyrene, C as 1-bromo-4-(1-bromoethyl)benzene, and states that A and C are position isomers).

Let us analyze the reaction sequence step-by-step:

Step 1: Identify Reactant A
From the question image, the starting compound (Reactant A) is 1-bromo-4-(2-bromoethyl)benzene. It contains a benzene ring with a bromine atom (-Br) at the para-position and a 2-bromoethyl group (-CH2CH2Br) at the opposite position.

Step 2: Elimination Reaction to form B
When Reactant A is treated with alcoholic sodium hydroxide (NaOH(alc)), a strong base, it undergoes dehydrohalogenation (an E2 elimination reaction). The base abstracts a proton from the carbon beta to the leaving group on the side chain:
-CH2-CH2Br+OH--CH=CH2+H2O+Br-
This elimination occurs on the alkyl side chain rather than the aromatic ring because aryl halides do not undergo elimination under these conditions. Thus, compound B is 4-bromostyrene (or 1-bromo-4-ethenylbenzene), which features a vinyl group (-CH=CH2) attached to the para-position of the bromobenzene ring.

Step 3: Hydrohalogenation Reaction to form C
When 4-bromostyrene (B) is treated with hydrobromic acid in ether (HBr/Ether), it undergoes electrophilic addition across the carbon-carbon double bond. According to Markovnikov's rule, the electrophile (H+) adds to the carbon with more hydrogen atoms (the terminal carbon) to generate the more stable carbocation intermediate:
-CH=CH2+H+-CH+-CH3
This benzylic carbocation is highly resonance-stabilized by the aromatic ring. The nucleophile (Br-) then attacks the carbocation to form the major product:
-CH+-CH3+Br--CH(Br)-CH3
Therefore, compound C is 1-bromo-4-(1-bromoethyl)benzene.

Step 4: Relationship between A and C
Let us compare the structures of compound A and compound C:
- Compound A: 1-bromo-4-(2-bromoethyl)benzene
- Compound C: 1-bromo-4-(1-bromoethyl)benzene
Both compounds share the same molecular formula (C8H8Br2) but differ in the position of the bromine atom along the ethyl chain (carbon 2 in A versus carbon 1 in C). Therefore, compounds A and C are position isomers.

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