Problems Set Week 6

1. Referring to step 1 (conversion of (1) to (3))

a. How many equivalents of stannous chloride are used to reduce nitrobenzene to aniline. How many electrons are transferred?

b. What is the function of the concentrated hydrochloric acid?

c. What is the function of the potassium hydroxide solution?

d. Why is potassium carbonate used to dry the organic layer in step 1?

2. Referring to step 2 (conversion of (3) to (4))

a. Why is sodium acetate used in the reaction?

b. Why are anhydrous conditions used in this step?

c. Why do you use chloroacetyl chloride in this reaction and not the chloroacetic acid?

d. Why is only the amide formed an not the S_N2-substitution product?

3. How can you prove that the C-N bond in an amide contains a partial double bond character (two techniques)? Explain briefly.