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Organic Chemistry - Stepweise mechanism, relative reactivity

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1. Write a detailed, stepwise mechanism to account for the following reaction. Be sure to include ALL the components of the mechanism.

CH3CH2CH3 + BR2 -> CH3CHBrCH3 + HBr

2. When 2, 2-dimethylbutane is subjected to free radical chlorination, the relative reactivity of the types of hydrogen's is as shown below.

Type of Hydrogen Relative reactivity
1 1.0
2 3.8
3 5.0

a. provide structures of each of the monochlorination products that would result.
b. Estimate the relative amount of each product that would result. Please show all of your math!

3. Consider the following 3 step mechanism for the reaction of A through intermediates B and C to produce D.

Reaction Step E subscriptA Triangle symbol H (kcal/mol)
A -> B 15 13
B -> C 10 -6
C -> D 2 -20

a. Draw the reaction energy diagram for this reaction mechanism. In your diagram, label for each step
Triangle symbol H (include signs)
E subscript A
Transition states
b. Which step is rate determining step? Explain your reasoning.
c. As a chemical engineer, your job is to speed up this reaction. How might you accomplish this?

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Solution Summary

Various questions in organic chemistry. The stepwise mechanism and relative reactivity are determined.

Solution Preview

Please refer to the attached file. Cheers.


The structure of 2,2-dimethylbutane is as follow:


The oval shown in blue is for type 1, black is for type 2, and red for type 3. The assignment is like so because the ...

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