Advices For Studying Organic Chemistry

Figure 6.11 Steric effects in the SN2 reaction.

CH 3 –Br CH 3 CH 2 –Br (CH 3 ) 2 CH–Br (CH 3 ) 3 CCH 2 –Br (CH 3 ) 3 C–Br

2. SN1 Reactions:
   
   
   1. The primary factor that determines the reactivity of organic substrates in
      an SN1 reaction is the relative stability of the carbocation that is formed.
   
   
   
   

Table 6A Relative rates of reaction of some alkyl halides with water:

Alkyl halide^ Type^ Product Relative rate of reaction^

CH 3 Br Methyl CH 3 OH 1.0

CH 3 CH 2 Br 1° CH 3 CH 2 OH 1.0

(CH 3 ) 2 CHBr 2° (CH 3 ) 2 CHOH 12

(CH 3 ) 3 CBr 3° (CH 3 ) 3 COH 1,200,000

2) Organic compounds that are capable of forming relatively stable carbocation

can undergo SN1 reaction at a reasonable rate.

i) Only tertiary halides react by an SN1 mechanism for simple alkyl halides.