Question

sodium bicarbonate = mild base (a) (15pts) Using what you have learned in Chapter 8 about the addition reactions of halogens with alkenes draw a complete arrow-pushing mechanism for this process to include the following: • Show all arrows for each mechanistic step, to illustrate correct electron flow • Structures of all reaction intermediates formed in the mechanism must be shown correctly, including the key cyclic iodonium ion intermediate • Underline the iodonium ion intermediate that is formed in the reaction • Stereochemistry of reaction intermediates consistent with the product stereochemistry shown • Formal charges where applicable (b) (2pts) Circle the correct option to describe the overall stereospecificity of this reaction. Syn-addition or Anti-addition (c) (3pts) Carbocation rearrangements are not possible in this reaction. This is due to the fact that a cyclic halonium ion intermediate forms, rather than a more traditional carbocation intermediate. In one sentence, explain why the cyclic halonium ion intermediate in general is considered more stable than a carbocation, and in turn prevents any possible rearrangement from happening in this reaction?

          sodium bicarbonate = mild base
(a) (15pts) Using what you have learned in Chapter 8 about the addition reactions of halogens with alkenes draw a complete arrow-pushing mechanism for this process to include the following:
• Show all arrows for each mechanistic step, to illustrate correct electron flow
• Structures of all reaction intermediates formed in the mechanism must be shown correctly, including the key cyclic iodonium ion intermediate
• Underline the iodonium ion intermediate that is formed in the reaction
• Stereochemistry of reaction intermediates consistent with the product stereochemistry shown
• Formal charges where applicable
(b) (2pts) Circle the correct option to describe the overall stereospecificity of this reaction.
Syn-addition or Anti-addition
(c) (3pts) Carbocation rearrangements are not possible in this reaction. This is due to the fact that a cyclic halonium ion intermediate forms, rather than a more traditional carbocation intermediate. In one sentence, explain why the cyclic halonium ion intermediate in general is considered more stable than a carbocation, and in turn prevents any possible rearrangement from happening in this reaction?

sodium bicarbonate = mild base
(a) (15pts) Using what you have learned in Chapter 8 about the addition reactions of halogens with alkenes draw a complete arrow-pushing mechanism for this process to include the following:
• Show all arrows for each mechanistic step, to illustrate correct electron flow
• Structures of all reaction intermediates formed in the mechanism must be shown correctly, including the key cyclic iodonium ion intermediate
• Underline the iodonium ion intermediate that is formed in the reaction
• Stereochemistry of reaction intermediates consistent with the product stereochemistry shown
• Formal charges where applicable
(b) (2pts) Circle the correct option to describe the overall stereospecificity of this reaction.
Syn-addition or Anti-addition
(c) (3pts) Carbocation rearrangements are not possible in this reaction. This is due to the fact that a cyclic halonium ion intermediate forms, rather than a more traditional carbocation intermediate. In one sentence, explain why the cyclic halonium ion intermediate in general is considered more stable than a carbocation, and in turn prevents any possible rearrangement from happening in this reaction?

Added by Heather W.

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