Which member of each of the following pairs of reactions willoccur most rapidly,

Question

Which member of each of the following pairs of reactions willoccur most rapidly, and by what mechanism. Justify yourchoice. a. i. (CH3)3CCH2Cl (CN- ; ethanol)    ii. PhCH2Cl (CN-; ethanol) b.i. CH3CH2CH2CH2Br (CN-;((CH3)2N)3PO     ii.CH3CH2CH2CH2Br(CN-; CH3OH) c. i. (CH3)3COH (H3O+; 25o C)    ii.CH3CH2CH2CH2OH (H3O+; 25o C) Please help, will rate lifesaver. The stuff in brackets goesabove and below the arrows, respectively) Which member of each of the following pairs of reactions willoccur most rapidly, and by what mechanism. Justify yourchoice. a. i. (CH3)3CCH2Cl (CN- ; ethanol)    ii. PhCH2Cl (CN-; ethanol) b.i. CH3CH2CH2CH2Br (CN-;((CH3)2N)3PO     ii.CH3CH2CH2CH2Br(CN-; CH3OH) c. i. (CH3)3COH (H3O+; 25o C)    ii.CH3CH2CH2CH2OH (H3O+; 25o C) Please help, will rate lifesaver. The stuff in brackets goesabove and below the arrows, respectively)

Explanation / Answer

(a) In both the cases they forming alkyl cyanide throughthe replacement of Cl - by CN -.During this process carbonium ion isformed.Among  (CH3)3CCH2+    & PhCH2+       ,PhCH2+ is more stable.So,  PhCH2Cl (CN- ;ethanol) reaction is more rapid. The order of stability of carbonium ions is       Phenyl > allyl > tertiary> secondary > primary       Phenyl > allyl > tertiary> secondary > primary (c)The order of dehydration of alcohols is givenby          Tertiary > Secondary > Primary

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