CHEM 203

Midterm Exam 2
November 19, 2015

Your name:

This a closed-notes, closed-book exam

You may use your set of molecular models

This document contains 7 pages

Time: 1h 30 min

1. ________ / 10

2. ________ / 15

3. ________ / 15

4. ________ / 20

5. ________ / 20

6. ________ / 20

TOTAL ________ / 100

This exam counts for 18.75% of your CHEM 203 final grade
Chem 203 midterm exam 2 p. 2 of 7

1. (10 pts.) The reaction of cyclopentene with O3 and then Zn / H+, followed by CH3MgBr and
then mild H3O+, affords two products. Draw the structures of these in the appropriate boxes:
product 1 product 2

1. O3
2. Zn, H+
+
3. CH3MgBr
then mild H3O+

2. (15 pts.) Inside the appropriate boxes, draw:

a. The structure of an alkene that produces the same alcohol upon reaction with either H2O
and H2SO4, or with BH3 followed by H2O2 and aqueous NaOH, and that of an alkene that
produces two different alcohols under the same conditions:
produces the same alcohol produces two different alcohols

b. The structure of an alkyne that contains at least 3 C atom, and that affords an achiral
product upon reaction with Na in liq. NH3 followed by Br2, and that of an isomeric
alkyne that yields a chiral product under the same conditions:
gives an achiral product gives a chiral product

c. The structure of an alkane that is a good substrate for radical bromination, and that of an
alkane that is a poor substrate for radical bromination:
good substrate for radical bromination poor substrate for radical bromination
Chem 203 midterm exam 2 p. 3 of 7

d. The structure of an alkyl halide that is likely to undergo nucleophilic substitution by the
SN2 mechanism, and that of an alkyl halide that is likely to undergo nucleophilic
substitution by the SN1 mechanism.
likely to react by SN2 likely to react by SN1

e. The structure of a chiral alkyl iodide that affords an achiral product upon reaction with
CH3-CH2-MgBr in the presence of CuBr:
structure of the alkyl iodide in question

3. (15 pts.) In the appropriate boxes below, draw the structure of: (i) an alkyl halide that yields
one compound as the major product of treatment with KOH in ethanol, but an isomeric
compound as the major product of treatment with potassium tert-butoxide; (ii) the major
product obtained upon reaction of the above alkyl halide with KOH in ethanol; (iii) the major
product obtained upon reaction of the above alkyl halide with potassium tert-butoxide.
Finally, draw an accurate mechanism for the formation of the two products:
major product from structure of the alkyl major product from
KOH in ethanol halide in question tert-BuOK

KOH OK

ethanol

mechanisms:
Chem 203 midterm exam 2 p. 4 of 7

4. (20 pts.) Provide the structure of the major product expected from the following reaction
sequences. If no overall change is expected, answer "NO REACTION." Important:
compounds incorporating multiple stereogenic centers must be drawn with the correct
relative configuration.
Note: it is understood that chiral compounds will be obtained as racemic mixtures.

1. BH3
2. H2O2, aq. NaOH
a.
O 3. NaH
4. CH3I

1. HCl
2. Mg
b.
3. CO2
4. mild H3O+

1. HBr, radical
initiator
c.
2. Na+
3. H2, Pt

1. NBS, hν
CH3
2. CH3ONa
d.
3. NBS, hν
4. CH3SNa

1. Br2, CH3OH
2. NaN3
e.
3. Zn, H+
Chem 203 midterm exam 2 p. 5 of 7

5. (20 pts.) Propose a method to achieve the transformations shown below. Indicate all the
reagents, in the correct order, that are required to induce each transformation. Present your
answer as a numbered list displayed above / below each reaction arrow. If a product appears
to be unavailable from the indicated starting material by any method known to you, write
"INACCESSIBLE" on the reaction arrow
Note: it is understood that chiral compounds will be obtained as racemic mixtures.

OH
a.

HO
H
b.
H
OH

OH
c.

H H

d.
OH OH
H H

Br Cl
e.
Chem 203 midterm exam 2 p. 6 of 7

6. (20 pts.) Propose a method for the preparation of compounds a. – e. below starting ONLY
with methane (CH4) and acetylene (H–C≡C–H) as the source of carbon atoms. You may use
any additional reagent that might be needed (e.g., borane, HCl, Mg, H2O2, potassium tert-
butoxide, etc.). Present your answer as a clear flowchart that shows all intermediate steps and
products. Substances obtained in a prior sequence may be used in later sequences. It is not
necessary to draw mechanisms

a. O

OH

OH
b. OH
Chem 203 midterm exam 2 p. 7 of 7

c.
OH

OH
H
d.
H
Cl

Br
H
e.
H
Br