Exam

#2 Practice

I. Classify each of the designated carbon atoms with an arrow as either;
R, S or achiral.


b)

c) d)
a) N(CH3)3
OH OH

Cl

Cl

CH3



II. Determine the relationship between each pair of compounds in the boxes below.
Use the following as classifications: enantiomers, diastereomers, chiral
or the same molecule.


a) Br Br
Br Br
b)
Br Br


Br Br
OH OH




c) d)
Cl CH3 CH
Cl
CH3 3
OH
CH3
OH




 III. Circle the most stable conformation in each of the following pair of compounds.
If the two compounds have very similar energies circle them both. Also label
each conformer as either chiral or achiral.


a)



chiral or achiral?
Br vs


Br






b) Br
Br
Br

vs chiral or achiral?
Br








c)



chiral or achiral?
vs








 IV. From the conditions below select those that would be appropriate to achieve the
following transformations in good yield. More than one may be used. Use the letter
designation to write the conditions over the arrow.

a)
+



OH OH



b)


OH




c)
+
OCH3

OCH3




CH3OH HBr 1) Hg(OAc)2 / THF, H2O
A H2SO4
D CH2Cl2
G 2) NaBH4 / NaOH

H 2O 1) O3, -78oC / CH2Cl2 H2
B H2SO4 E H Pd (C)
2) (CH3)2S

HBr 1) O3, -78oC / CH2Cl2 1) BH3 / THF

C CH3-O-O-CH3 F I 2) H2O2 / NaOH
2) H2O2 / H2O



V. a) Draw the structure of the product(s) formed in the following transformation in
the box. Provide all stereochemical outcomes.
Note: A ring is formed.

OH
H2SO4 cat.

b) Provide an arrow-pushing mechanism for the formation of the product(s) formed
in the transformation above. Provide explicit stereochemical outcomes on each step
of the reaction.


























 VI. For each of the following reactions provide the alkene starting material and
conditions. Selection of the starting material and conditions should produce the
expected product(s) as the major product(s).

O O







HO OH

CH3OH HBr 1) Hg(OAc)2 / THF, H2O
A H2SO4
D CH2Cl2
G 2) NaBH4 / NaOH

H 2O 1) O3, -78oC / CH2Cl2 H2
B H2SO4 E H Pd (C)
2) (CH3)2S


HBr 1) O3, -78oC / CH2Cl2 1) BH3 / THF
C CH3-O-O-CH3 F I 2) H2O2 / NaOH
2) H2O2 / H2O


VII. A mixture of variable composition of compounds A & B, shown below, was
treated with 1) BH3 / THF then, 2) H2O2 / NaOH.

a) Draw the structure of the products of the reaction in the corresponding boxes.
Label any stereogenic center and identify whether or not the products are chiral or
achiral.

1) BH3 / THF
+
2) H2O2 / NaOH

Compound A

1) BH3 / THF
2) H2O2 / NaOH +

Compound B

b) If the resulting product mixture has an enantiomeric excess, how would you use
that information to help identify the starting mixture composition? Briefly explain.















VIII. The reaction of 1-methylcyclohexene with the borane derivative shown below
produces a mixture of (S, S)-2-methylcyclohexanol and (R, R)-2-methylcyclohexanol
after reaction with a strongly basic hydrogen peroxide solution.

+
+
B

Borane derivative A Borane derivative B


H2O2 / NaOH H2O2 / NaOH







+





(S, S)-2-methylcyclohexanol (R, R)-2-methylcyclohexanol

2.2% 97.2%

a) Draw in each box the corresponding compounds formed in the reaction.


b) As you can see the reaction produces an enantiomeric excess of 95% of the (R, R)-
2-methylcyclohexanol. Which step in the reaction is responsible for producing this
enantiomeric excess; the hydroboration or the oxidation? Explain in one sentence
or two.