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Boston University CH203 Section B Exam 1 October 1, 2014

Name: ______ANSWER KEY_______________

There are eight (8) pages in the exam. Write your name clearly above
and initial each page. Only the front of each page will be graded.

1. Sucralose (shown below), a chlorinated sugar sold under the brand name
Splenda, was developed by chemists trying to develop a better insecticide.
Determine whether the indicated carbons are R, S, or neither. (2 pt each)

A R
B S
C neither
D R
E R







2. Shown below are four possible resonance contributors to acetonitrile oxide, CH3CNO:



a. Which structure is invalid? (2 pt) A B C D
b. Rank the valid contributing structures in order of importance: (2 pt) A > D > C

3. Shown below is the antibiotic tetracycline, which is obtained from soil bacteria. Nubian
mummies studied in the 1990s were found to contain significant levels of tetracycline; the beer
brewed at the time could have been the source. Make an X next to the name of any functional
group found in tetracycline.

Carboxylic amide __X___
Aldehyde _____
Ketone __X___
Carboxylic acid _____
Carboxylic ester _____
Amine __X___
Alcohol __X___
H
3
C C N O H
3
C C N O H
3
C C N O H
3
C C N O
A B C D

1 _______
2 _______
3 _______
4 _______
5 _______
6 _______
7 _______
8 _______
Total _______
O
O
O
Cl
HO
HO
OH
OH
HO
Cl
Cl
E
A
B
C
D

+1 for each right choice
-1 for each wrong choice


2
2
4. Calculate the formal charge on oxygens 1, 2, and 3 in ozone: (3 pt)



1 0 2 +1 3 -1


5. What is the hybridization of oxygen 2? (1 pt) __sp
2
______

6. What is the approximate O-O-O bond angle? (1 pt) __120
o
___

7. Methanol is protonated by strong acids to give the cation:


What is the shape of the groups (including any lone pairs) around the carbon atom? (1 pt)
tetrahedral

What is the hybridization of carbon? (1 pt)
sp
3


What is the shape of the groups (including any lone pairs) around the oxygen atom? (1 pt)
tetrahedral

What is the hybridization of oxygen? (1 pt)
sp
3


O O O
1 2 3
H
3
C OH
2


3
3
8. Examine the following cyclohexane rings and count up the number of 1,3-diaxial interactions
and gauche interactions in each. (1 pt each)




A:
1,3-diaxial CH
3
, H __4___
1,3-diaxial CH
3
, CH
3
__0___
gauche CH
3
, CH
3
__1___

B:
1,3-diaxial CH
3
, H __2___
1,3-diaxial CH
3
, CH
3
__0___
gauche CH
3
, CH
3
__3___

C:
1,3-diaxial CH
3
, H __4___
1,3-diaxial CH
3
, CH
3
__1___
gauche CH
3
, CH
3
__1___
CH
3
CH
3
CH
3
CH
3
CH
3
CH
3
H
3
C
H
3
C
CH
3
H
3
C
CH
3
CH
3
A B C


4
4
9. R or S? (2 pt each)



R S R S





10. Convert the planar cyclohexane structure to the two interconverting chair conformations and
predict which conformation would be more stable. Label all groups in the most stable
conformation as axial or equatorial. (8 pt)















11. Draw the structure which corresponds to 4-ethyl-6,6-dimethyl-heptane and give it a correct
IUPAC name. (4 pt)




4-ethyl-2,2-dimethylheptane


F CH
3
Br
Br
O
H
CH
3
NH
2
2
H
OH
H
H
H
3
C
H
CH
3
H
OH
H
H
axial
axial
equatorial
more stable
+2 for each correct chair
+3 for choosing the more stable conformation
+3 for correct axial and equatorial labels
H
3
C CH
3
CH
3
OH
CH
3
+2 structure
+2 name


5
5
12. Draw the structure which corresponds to 3-chloro-2-bromo-1-dimethylcyclohexane and give
it a correct IUPAC name. (4 pt)















13. For the following structure, check all the descriptions that apply to it.



__X___Is achiral
______Has an enantiomer
__X___Is a meso compound
__X___Has at least one chiral diastereomer
__X___Contains at least one R stereocenter
__X___Has one achiral diastereomer


O
Br
Br
CH
3
H
3
C
OH HO
+2 structure
+2 name
CH
3
Br
Cl
+2 for each correct choice
-2 for each incorrect choice
2-bromo-1-chloro-3-methylcyclohexane


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6
14. For the following structure, check all the descriptions that apply to it.



______Is achiral
__X___Has an enantiomer
______Is a meso compound
______Has at least one chiral diastereomer
__X___Contains at least one R stereocenter
__X___Has one achiral diastereomer

15. Which of the following statements regarding optical rotation is not true? (4 pt) __b_____
a. All (+) enantiomers are dextrorotatory.
b. All R enantiomers are dextrorotatory.
c. All (!) enantiomers rotate plane-polarized light in a counterclockwise direction.
d. All (+) and (!) enantiomers rotate plane-polarized light in opposite directions.

16. Carvone is found in many essential oils. R-()-carvone smells like spearmint and has a ["] =
-60
o
. Its mirror image, S-(+)-carvone, smells like caraway.

You are given an oily substance which smells like a mixture of spearmint and caraway seeds.
From this you deduce that it is a mixture of R- and S-carvone. You determine the specific
rotation of the mixture in your polarimeter and find that ["] = +15
o
.


F
CH
3
CH
3
F
+2 for each correct choice
-2 for each incorrect choice


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16 (continued).
What % of the mixture is a racemic mixture? (4 pt) ___c____
a. 25
b. 50
c. 75
d. 100


17. What is the % of R-()-carvone in the total mixture? (4 pt) ___b___
a. 25
b. 37.5
c. 33.3
d. 50

18. A compound with a central carbon participating in two double bonds with different carbons
(i.e. a 1,2-diene) is known as an allene, as shown below. What is the hybridization of each
carbon listed below? (3 pt)

Benzene ring carbons sp
2

Allene end carbons sp
2

Allene central carbon sp

Is this allene: (4 pt) __a___
a. chiral,
b. achiral,
c. a meso compound, or
d. none of the above








C
CO
2
Me
MeO
2
C
C
CO
2
Me
MeO
2
C
C
MeO
2
C
CO
2
Me
Nonsuperimposable mirror images


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8

19. Isonitriles such as 1 are often found in marine invertebrates, where they function as defensive
compounds against predators.
Draw all stereoisomers of 1. (Ignore the alkene stereochemistry, and
you may use R for the long diene chain instead of drawing the
whole thing out.) (3 pt)
What type of stereoisomer is each, relative to 1? (3 pt)




























20. Draw compound 1 in its most stable conformation. (Again, use R for the diene substituent.)
(3 pt)

R
H
H
3
C NC
H
R
H
3
C NC
original diastereomer
+3 for the (one) structure
+3 for diastereomer label
-2 for mentioning an enantiomer
-2 for mentioning meso
-1 for multiple, repeated, or incorrect drawings

H
CH
3
H
R