1. (3 pts ea) For each compound shown below, write the number of signals (unique resonances) expected for both the NMR

and for the NMR in the appropriate box provided. Ignore splitting for the purposes of this problem.

!

!

!

!

!

2. (2 pts ea) Determine the Index of Hydrogen Deficiency (IHD) for the following:

IHD =

IHD =

IHD =

3. a. (5 pts) Provide the product expected when the following alkyl bromide is heated in the presence of sodium ethoxide; be

aware of stereochemistry.

b. (10 pts) Provide a mechanism for this transformation that fully explains your answer for (a)

4. (20 pts) When 2-methyl-2-butene is treated with aqueous acid, two isomeric alcohols are formed in roughly an 80:20 ratio.

Provide the structures of these two products in the boxes below, and a mechanism that accounts for the formation of the major

product.

Minor

Major

5. (15 pts) On the next page you will find both proton NMR and IR spectra for the compound C9H12O. Using this information,

deduce the structure of the compound. Record all of your analytic data below; remember, MOST of the points for this

problem will be awarded for deducing the pieces, NOT the final structure. Be clear and logical. Put your final structure in the

box.

6. (10 pts) Provide a mechanism for the following transformation:

!"#$%&'$#()$*+,($-&.)$/"0$(%0&*%+$1"02$3#*$4"$567$-#*$1"02$8"#$1&'*$.0&4)4$"'$,*9$$

$$$$$$$

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Part 2. Multiple Choice Questions. For each of the questions below choose the best answer(s) AND MARK IT ON YOUR

SCANTRON. Some (BUT NOT ALL) of the questions will have more than one correct answer, and some will have partial

credit. For full credit, choose all those that you think are correct, BUT BE WARNED: questions marked with an asterisk (*)

have penalties associated with choosing a WRONG answer (approx. 2-5 points per wrong choice), so do NOT guess unless you

are fairly sure. A blank answer will not be counted as wrong.

1. Mark the letter A on your scantron for Question 1, bubble in A in the Test Form Field, and bubble in your Sequence number

in the Exam Number Field (3 pts for doing all three).

2*. Which of the following alkenes shown below are expected to form as the major product(s) when the alcohol below is

heated in aqueous acid:

a.

b.

c.

d.

e.

3. A hydrocarbon with the molecular formula C7H12 exhibits the following spectroscopic data: 1H NMR ! = 1.3 (m, 2H), 1.7

(m, 4 H), 2.2 (m, 4H), and 4.8 (quin, J = 3 Hz, 2H) ppm; 13C NMR: ! = 26.8, 28.7, 35.7, 106.9, and 149.7 ppm. The IR

spectrum has key absorbances at 3072, 2950, and 1649 cm—1. Hydrogenation of the compound furnishes a product with the

molecular formula C7H14. Which structure is consistent with this data?

a.

b.

c.

d.

e. none of the above

4. Under special reaction conditions, !-pinene and "-pinene can be in equilibrium (caused to interconvert reversably). Using

your knowledge of alkene stability, which of the following would be true at equilibrium?

A) The !-isomer will predominate. B) The "-isomer will predominate.

C) The isomers would be equally favored. D) A third isomer would predominate.

E) None of the above is true.

Questions 5-8: For the following molecules, determine whether the indicated H’s are A) homotopic; B) enantiotopic;

or C) diastereotopic

5*.

6*.

7*.

8*.

9*. Which of the following are Z isomers?

Br

Cl CH3

H3CCO2H

H CH3

H3CN(CH3)2

H3CCH3

H

CO2H

C6H5H

H3CCHO

H3CCO2H

H

a) b) c)

d) e)

10*. Which one of the following would undergo E2 elimination most rapidly?

a.

b.

c.

d.

e. All would react at the same

rate

!