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NEET CHEMISTRYMedium

Identify Z in the sequence of reactions: CH3CH2CH=CH2HBr/H2O2YC2H5ONa+Z\text{CH}_3\text{CH}_2\text{CH=CH}_2 \xrightarrow{\text{HBr/H}_2\text{O}_2} \text{Y} \xrightarrow{\text{C}_2\text{H}_5\text{O}^-\text{Na}^+} \text{Z}

A

CH3-(CH2)3-O-CH2CH3\text{CH}_3\text{-(CH}_2)_3\text{-O-CH}_2\text{CH}_3

B

(CH3)2CH2-O-CH2CH3\text{(CH}_3)_2\text{CH}_2\text{-O-CH}_2\text{CH}_3

C

CH3(CH2)4-O-CH3\text{CH}_3\text{(CH}_2)_4\text{-O-CH}_3

D

CH3CH2-CH(CH3)-O-CH2CH3\text{CH}_3\text{CH}_2\text{-CH(CH}_3\text{)-O-CH}_2\text{CH}_3

Step-by-Step Solution

The sequence of reactions occurs in two steps:

  1. Step 1 (Formation of Y): But-1-ene (CH3CH2CH=CH2\text{CH}_3\text{CH}_2\text{CH=CH}_2) reacts with HBr\text{HBr} in the presence of a peroxide (H2O2\text{H}_2\text{O}_2). This addition follows the anti-Markovnikov rule (Kharash or peroxide effect), where the free radical mechanism leads to the bromide atom attaching to the terminal (less substituted) carbon atom . This yields 1-bromobutane as intermediate Y\text{Y}: CH3CH2CH=CH2+HBrPeroxideCH3CH2CH2CH2Br\text{CH}_3\text{CH}_2\text{CH=CH}_2 + \text{HBr} \xrightarrow{\text{Peroxide}} \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{Br} (Compound Y)

  2. Step 2 (Formation of Z): 1-bromobutane undergoes an SN2S_N2 nucleophilic substitution reaction (Williamson ether synthesis) with sodium ethoxide (C2H5ONa+\text{C}_2\text{H}_5\text{O}^-\text{Na}^+). The ethoxide ion attacks the primary carbon of the alkyl halide, displacing the bromide ion to form ethyl butyl ether as product Z\text{Z} : CH3CH2CH2CH2Br+C2H5ONa+CH3CH2CH2CH2-O-CH2CH3+NaBr\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{Br} + \text{C}_2\text{H}_5\text{O}^-\text{Na}^+ \rightarrow \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{-O-CH}_2\text{CH}_3 + \text{NaBr}

The product Z\text{Z} is CH3-(CH2)3-O-CH2CH3\text{CH}_3\text{-(CH}_2)_3\text{-O-CH}_2\text{CH}_3.

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