Question

I can't figure out the answer please help.

1. Which of the following would you expect to have the weakest C-X bond?
A)CH3Cl
B)CH3CH2Br
C)CH3F
D)CH3CH2I
E)(CH3)2CHBr


2. Which of the following haloalkanes would not undergo the reaction below?
R-X + CH3S^ ----> CH3SR + X^-
A)(CH3)2CHI
B)CH3Cl
C)CH3CH=CHBr
D)CH3CH2Br
E)CH3CH2CH2I

Answer 1

Here are a couple of clues (not answers):

1. One of the choices involves a Br atom bonded to a secondary carbon atom (one attached to two other carbon atoms). This is the one that forms the more stable carbonium ion, and the weakest C-Br bond.

2. CH3S^- would react most readily with the haloalkane that forms the least stable carbonium (R+) ion. Inversely, a primary haloalkane with the shortest carbon chain would be the least likely to react.

Answer 2

Sorry, my clue to the second question needs correction:
2. CH3S^- would react most readily with the haloalkane that forms the MOST stable carbonium (R+) ion. Inversely, a primary haloalkane with the shortest carbon chain would be the least likely to react.

Answer 3

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