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Consider the following sequence of react...

Consider the following sequence of reactions :
`C_6H_5CH_3overset(Cl_2)rarrp-ClC_6H_4CH_3overset(NBS)rarr(X) overset(Mg)rarr(Y)overset((i)"ethylene oxide")rarr(Z) `
Final product (Z) is

A

`p - ClC_6H_4CH_2CH_2OH`

B

`p- ClC_6H_4CH_2CH_2CH_2OH`

C

`p-(HOCH_2CH_2) - C_6H_4CH_2Br`

D

`p - (HOCH_2CH_2)-C_6H_4CH_3`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem step by step, we will analyze each reaction in the sequence provided and determine the final product (Z). ### Step 1: Chlorination of Toluene - **Reaction**: Toluene (C₆H₅CH₃) reacts with chlorine (Cl₂). - **Mechanism**: Toluene is an aromatic compound with a methyl group (–CH₃) that is ortho-para directing. Chlorination will predominantly occur at the para position due to steric hindrance at the ortho position. - **Product**: The major product formed is para-chlorotoluene (p-ClC₆H₄CH₃). ### Step 2: Bromination with NBS - **Reaction**: para-Chlorotoluene reacts with N-bromosuccinimide (NBS). - **Mechanism**: NBS facilitates benzylic bromination, which occurs at the benzylic position (the carbon adjacent to the aromatic ring). - **Product**: The product formed is p-ClC₆H₄CH₂Br (compound X). ### Step 3: Formation of Grignard Reagent - **Reaction**: Compound X (p-ClC₆H₄CH₂Br) reacts with magnesium (Mg). - **Mechanism**: The reaction of an alkyl halide with magnesium forms a Grignard reagent. - **Product**: The product formed is p-ClC₆H₄CH₂MgBr (compound Y). ### Step 4: Reaction with Ethylene Oxide - **Reaction**: Compound Y (p-ClC₆H₄CH₂MgBr) reacts with ethylene oxide (C₂H₄O). - **Mechanism**: The Grignard reagent acts as a nucleophile and attacks the electrophilic carbon in ethylene oxide, leading to ring opening and formation of a new carbon-carbon bond. - **Product**: The product formed is p-ClC₆H₄CH₂CH₂CH₂O⁻MgBr (compound Z). ### Step 5: Hydrolysis of the Grignard Reagent - **Reaction**: Compound Z undergoes hydrolysis. - **Mechanism**: Hydrolysis of the Grignard reagent involves the addition of water (H₂O) to convert the alkoxide into an alcohol. - **Final Product**: The final product formed is p-ClC₆H₄CH₂CH₂CH₂OH (compound Z). ### Conclusion The final product (Z) is para-chlorobutanol, specifically p-ClC₆H₄CH₂CH₂CH₂OH. ### Answer The final product (Z) is **p-Chlorobutanol**. ---
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