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Organic Reactions and Mechanisms

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I am totally confused on the topic of matching mechanistic class. Can you help me with an explanation, answering the attached problem below. This would be greatly appreciated.

Thank you.

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Solution Preview

Please see the attachment(s) for two handwritten sets of diagrams and the diagrams for the answers to the problem.

a) This is just an example of nucleophilic substitution. Show with arrows the conjugated electron pull towards carbonyl oxygen in 2-cyclohexenone, making C-3 electron deficient, where the nucleophile will attack.
[Diagram in attachment "Answer to Matching Mechanistic Class"]

b) This is a case of Schmidt rearrangement. The mechanism is as follows:
In the reaction mechanism for the ketone Schmidt reaction, the carbonyl group is activated by protonation for nucleophilic addition by the azide, forming intermediate 3, which loses water in an elimination reaction to temporary imine 4, over which one of the alkyl groups migrates from carbon to nitrogen with loss of ...

Solution Summary

This solution contains all necessary steps in details to solve a bunch of organic chemistry problems and reaction mechanism.

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Organic Reaction Mechanisms

Written Assignment 6

Submit your solutions to the following problems. Show all work where applicable .Answers alone are not acceptable.

1. Select an alkyl halide and a nucleophile that will give each of the following products:

d. (CH3)2CHCH2OH

2. Draw out each of the following equations in a way that shows clearly the stereochemistry of the reactants and products.

a. (R)-3-chlorohexane+sodium methoxide(in methanol) 3-methoxyhexane
b. (S)-2-chlorobutane+methanol 2-methoxybutane

3. Determine the order of reactivity for (CH3)2CHCH2Br, (CH3)3CBr, and CH3CHBrCH2CH3
Reacting with

a. CH3OH(methanol)
b. NaSH(sodium hydrosulfide)

4. Tell ALL possible products you expect and by what mechanism they are formed for each of the following reactions:


5. Give the structures of all possible products when 2-chlorobutane reacts by the E-2 mechanism.

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