1. Recalling that nucleophilic substitution reactions only occur at sp3 hybridiz

Question

1. Recalling that nucleophilic substitution reactions only occur at sp3 hybridized carbon atoms containing a leaving group, are there any molecules from table 1 that you suspect will not undergo nucleophilic substitution?

2. Predict the order of both SN1 and SN2 reactivity for the alkyl halides in table 1.

Table 1: SN2 Reactivity Structure Name 2 CH3CH2CH2CH2Br n-Butyl Bromide 3 CH3CHBrCH2CH3 sec-Butyl Bromide 4 (CH3)2CHCH2Br Isobutyl Bromide 5(CH3)3CC 6 CH3CH=CHBr tert-Butyl Chloride Propenyl Bromide Benzyl Chloride 8 CH2-CHCH2Br Allyl Bromide 9 C6H5Br Bromobenzene

Explanation / Answer

1) bromo benzene , propenyl bromide wii not undergo nucleophillic substitution because leaving group attached to Sp2 c atom.

2) Benzyl bromide > allyl bromide > tert-butyl chloride > sec-butyl bromide > isobutyl bromide > n-butyl bromide > n-butyl chloride. SN1 order.    more the stability of carbocation faster the SN1 reaction.

Benzyl bromide < allyl bromide < tert-butyl chloride < sec-butyl bromide < isobutyl bromide < n-butyl chloride < n-butyl bromide. SN2 order.

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