Organic Chemistry 1 test

Q1. How many stereoisomers are possible for butane-2,3-diol?

Draw all possible stereoisomers of butane-2,3-diol.

7 pts

Or, Students can draw the perspective formula as well

How many E-2 products are possible in the following reaction? JUSTIFY your answer. 4 pts

How could IR spectroscopy be used to distinguish between the following pair of compounds?

CH3COCH CHCH2CH3 and CH3COCH2CH2CH CH2

3 pts

Identify the following solvents as protic or aprotic solvent. 4 pts

CH3CH2OH H2O

CH3COOH CH3SOCH3

Q 2

Draw the substitution products for the following reaction: 6 pts

Draw all possible elimination products for the reactions shown below. Circle the major product and

explain your choice. 9 pts

Provide the mechanism to rationalize the formation of the products for the reactions shown below:

7 pts

Mechanism:

Q 3

Choose the reagent to accomplish the following reaction. Propose a mechanism.

What will be the stereochemical outcome of the reaction? 10 pts

The product will be the mixture of enantiomers ( racemic mixture).

Draw all possible E2 products for the following reaction. Circle the most stable product. Explain your

choice. 10 pts

EXTRA CREDIT: 5 pts

The compound below has the molecular formula C6H11BrS. This compound reacts with

NaOH in aqueous ethanol to form compound A with the molecular formula C6H10S. What is the

structure of compounds A? Can you draw the mechanism for the formation of A?