Organic Chemistry Test 2 Questions

 

Below are three chemical reactions. Choose one of these reactions.

 

  1. Give the complete curved-arrow mechanism for the reaction, and give the name (i.e., SN1, SN2, E1, E2) for the type of substitution/elimination pathway the reaction follows.
  2. Provide about a paragraph of explanation for what happens in the reaction. What are the factors that particularly favor the pathway and mechanism you described in (1)? In general, explain why you think that the reaction you picked proceeds by the mechanism you drew. Do you expect any side/minor products to be formed? If so, what is the name of the reaction that forms the side product? Draw the structure of the minor product.

 

  1. Label the groups 1-4 and assign the stereochemistry (R/S) of any stereocenters in the molecule marked with a star (*) for your chosen reaction.

 

  1. List any important IR peaks which will be present in the product. Give the number of NMR peaks which the product will have. For the NMR peaks, show your work by drawing in the H atoms and labeling/circling them to show which hydrogens are in the same group.

 

Br SH- * SH

a)

Na

+

DMSO

Br H2O OH

b)

acetone,

heat

*

c)

Br

KOH

ethanol,

heat

*

 

 

 

 

To ensure that you have plenty of space, I recommend you provide your answer on a separate sheet of paper. Note: The above reactions are not balanced. Only organic products are shown. Salts, HBr, etc. are left out, as is common in organic chemistry line reactions.

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