(a) Draw the structure of major Mono halogen product formed in the following reaction: (b) Predict the order of reactivity of the following compounds in SN1 reaction:C6H5CH2Br, C6H5C(CH3) (C6H5) Br, C6H5CH(C6H5) Br, C6H5CH(CH3) BrOR(a) Arrange the following in increasing order of boiling point:CH3CH2CH2CH2Br, (CH3)3 Br, (CH3)2C Br(b) Haloalkanes undergo nucleophilic substitution whereas haloarenes undergo electrophilic substitution. Explain.

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(a) Draw the structure of major Mono halogen product formed in the following reaction:
(b) Predict the order of reactivity of the following compounds in S_N1 reaction:
C₆H₅CH₂Br, C₆H₅C(CH₃) (C₆H₅) Br, C₆H₅CH(C₆H₅) Br, C₆H₅CH(CH₃) Br
OR
(a) Arrange the following in increasing order of boiling point:
CH₃CH₂CH₂CH₂Br, (CH₃)₃ Br, (CH₃)₂C Br
(b) Haloalkanes undergo nucleophilic substitution whereas haloarenes undergo electrophilic substitution. Explain.

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Detailed Solution

(a)

(b) C₆H₅C(CH₃) (C₆H₅)Br > C₆H₅CH(C₆H₅)Br > C₆H₅CH(CH₃)Br > C₆H₅CH₂Br

(a) (CH₃)₂C.Br < (CH₃)₂.CHCH₂.Br < CH₃CH₂CH₂CH₂Br

(b) Haloarenes (chlorobenzene) is a resonance hybrid of the following five structures:

Resonance leads to

i. Lowering of energy

ii. Greater stability.

iii. Greater electron density at these ortho and para positions increases

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