Chem 22 - Test #3
June 1, 2015 This test consists of a combination of multiple choice and other questions. There should be a total of sixteen questions
on eight pages; please check now to make sure that they are all here. Do not use your own tables, scratch paper or other
information. Please turn off all cell phones, pagers and other communication devices; they will be confiscated if they
make noise. No food. No water. No gum. No bathroom breaks. No templates. No models. Calculators OK if used
appropriately. The test will end 135 minutes after it starts. An information sheet will be handed out separately.
Multiple Choice Questions
These nine questions are worth three points each, for a total of 27 points. Unless it is stated otherwise in a given
problem, there is only one correct answer for each question. Answer each question by circling all letter(s)
corresponding to the correct choice(s); in other words, if more than one answer is correct, you should circle all of the
correct ones. It is not necessary to show work for these questions; however, you may write on the exam.
1. Which of the following is the weakest base?
a.
b.
c.
d.
e.
2. Which reagents will convert the reactant to the product shown in an efficient manner?
a. NaCl/∆
b. SOCl2, pyridine
c. HCl(aq)/∆
d. 1. NH3; 2. SOCl2
e. 1. H3O+/∆; 2. SOCl2
f. None of these will work.
3. What is the structure of the reactant in the following intramolecular aldol condensation?
.
a
d .
b.
e.
c.
f. None of these.
Page 1 of 7 – Test 3B – Chem 22 (Spring 2015)
4. Which of the following can successfully react in a self Claisen condensation? More than one answer may be correct.
a.
b.
c.
d. None of them 5. Which of the following can successfully react in a self aldol addition reaction? More than one answer may be correct.
a.
b.
c.
d. None of them
6. What are the major products in the following reaction?
a.
b.
c. both sets of products are formed in roughly equal amounts
7. What is the major organic product in the reaction below?
a.
b.
c.
d.
e.
f. none
8. Which of the following could be prepared via a Michael reaction using an enolate (not having to resort to a Stork
enamine synthesis)? More than one answer may be correct.
a.
b.
c.
d. None of them
Page 2 of 7 – Test 3B – Chem 22 (Spring 2015)
9. Which of the following would have to be prepared using a directed aldol addition (e.g, using LDA to make the
enolate) to avoid unwanted side products? Assume that the conditions do not promote the elimination step. More
than one answer may be correct.
a.
b.
c.
d. None of them
Other Questions
Each of the following questions is worth the indicated number of points, for a total of 73 points. Please be sure
to provide all of the information requested for each question.
10. 5 points Name each compound.
a.
b.
11. 6 points Write a mechanism that shows the formation of the organic product from the reactants. Include curved
arrows to show electron movement.
Page 3 of 7 – Test 3B – Chem 22 (Spring 2015)
12. 38 points Draw the structure(s) of the major organic product(s) derived from the original starting material that are
formed in each of the following reactions or reaction steps. The ones with one box are worth three points each. The
ones with two boxes are worth four points total, or two points per box.
a.
b.
c.
d.
Page 4 of 7 – Test 3B – Chem 22 (Spring 2015)
Problem 12 - continued
e.
f.
g.
h.
Page 5 of 7 – Test 3B – Chem 22 (Spring 2015)
Problem 12 - still continued
i.
j.
k.
13. 7 points Show how you would synthesize the product from the starting material given. Draw structures of any
intermediate products that could be isolated. Page 6 of 7 – Test 3B – Chem 22 (Spring 2015)
14. 5 points Show how the following transformation could be accomplished using a Stork enamine synthesis. You need
not show intermediate products and may, in fact, simply write the sequence of reagents over/under the reaction
arrow.
15. 7 points Write a mechanism that shows the formation of the organic product from the reactants. Include curved
arrows to show electron movement. The reaction is not necessarily fully balanced.
16. 5 points Show how you would use either the malonic ester or acetoacetic ester synthesis (whichever is appropriate)
to prepare the compound shown. You need not show intermediate products and may, in fact, simply write the
sequence of reagents over/under the reaction arrow. The structures of diethyl malonate and ethyl acetoacetate are
on the information sheet.
Page 7 of 7 – Test 3B – Chem 22 (Spring 2015)