- Joined
- Jun 13, 2009
- Messages
- 59
- Reaction score
- 0
- Points
- 0
- Pre-Dental
Advertisement - Members don't see this ad
Situation 1:
HC=CH
1) NaNH2, NH3 --> 2) CH3I ---> 3) CH3MgCl ---> MgCl-C=C-CH3 + CH4
(in ether)
Situation 2:
CH3-CH2-C=N:
1) CH3MgCl ---> 2) H3O+ --> CH3-CH2-C-CH3
||
O
The question is, why is it that in Situation 1, where the grignard is reacted with an alkyne, the MgCl attaches to the carbon compound (and not the methyl); whereas in Situation 2, where the grignard is reacted with a nitrile, the METHYL attached to the grignard reacts with the carbon compound to replace the N?
HC=CH
1) NaNH2, NH3 --> 2) CH3I ---> 3) CH3MgCl ---> MgCl-C=C-CH3 + CH4
(in ether)
Situation 2:
CH3-CH2-C=N:
1) CH3MgCl ---> 2) H3O+ --> CH3-CH2-C-CH3
||
O
The question is, why is it that in Situation 1, where the grignard is reacted with an alkyne, the MgCl attaches to the carbon compound (and not the methyl); whereas in Situation 2, where the grignard is reacted with a nitrile, the METHYL attached to the grignard reacts with the carbon compound to replace the N?
