CHM 211 (01) - Turnbull
FINAL EXAM
Fri., November 21, 2003
Answer Key
1. (11) Name the following molecules using IUPAC rules. In part a) only, assign E or Z
designations.
a)
b)
F
Cl
6-chloro-7-fluoro-4-methyl-6(E)-octen-1-yne
4-ethyl-1-isopropyl-5-methyl-1-cycloheptene
2. (4) Draw a Fischer projection for meso-1,2,3,4-tetrabromobutane
CH2Br
H
Br
H
Br
CH2Br
3. (8) A hydrocarbon of unknown structure has the formula C8H10. On catalytic hydrogenation
over Lindlar's catalyst, only one equivalent of H2 reacted. On hydrogenation over Pd, however, 2
equivalents of H2 reacted.
a) How many degrees of unsaturation does the molecule have?
four
b) How many triple bonds are present?
one
c) How many double bonds are present?
none
d) How many rings are present?
two
4. (3) True or False? A compound with an absolute configuration of (R) always will
rotate plane-polarized light in a clockwise direction.
5. (3) True or False? The rate of reaction for the SN1 reaction of water with 2-bromo-2methylpropane is proportional to [2-bromo-2-methylpropane][water]. Note: [ ] =
concentration.
6. (3) True or False? The rate of reaction for the SN2 reaction is faster in polar protic
solvents.
7. (3) True or False? For nucleophilicity, the general trend is "the weaker base, the better
the nucleophile."
8. (3) How many different monochloro derivatives are possible for the molecule shown?
a) two
b) three
c) four
d) five
O
O
9. (6) State whether (or not) the following pairs are resonance forms of one another.
a)
CH 2
CH 2
resonance
and
S
R'
S
R'
b)
R-N=C=O
and
NH 2
c)
not resonance
R C N O
NH2
not resonance
and
R
OH
R
O
10. (4) The degree of unsaturation (rings and/or multiple bonds) for the formula
C5H3ClFNO is:
a) four
b) 5
c) 6
d) 7
11. (3) What is the relationship between these structures?
a) constitutional isomers
b) same compound
c) enantiomers
d) diastereomers
H3 C
H3C
Cl
H
C CH
CH3
H3 C
CH3
CH CH
H3 C
Cl
12. (3) Cis-1,2-dichlorocyclohexane has?
a) One chlorine axial and the other equatorial
b) Both chlorines axial
c) Both chlorines equatorial
d) Both chlorines equatorial or axial
e) Any of the above depending on how the molecule flips
13. (9) Show an arrow (or arrows) indicating the movement of electrons (sharing) between each of
the reaction pairs shown. You need not show the consequence of your arrows.
a)
O
H-Br
b)
Cl
+
c)
BH3
H3C
H
14. (2.5) Draw the conjugate base of 1-heptyne.
C
C
15. (3) True or False? A meso compound must have a superimposable mirror image.
16. (4.5) For the following, circle all of the statements to the right which are correct.
BH3 then
HO
H
¥
¥
¥
¥
¥
¥
H
-
H2O2, OH
anti addition
syn addition
anti-Markovnikov
hydration
substitution
Markovnikov
17. (8) By assigning priorities to the groups attached, designate either E or Z or R or S (as
appropriate) to each of the following molecules. You must show all the priorities (#1 = highest) to
receive full credit.
a)
b)
1
Br
3
F
4
1
HO-C 2
O
(E)
4
(S)
HO 2
NH
CN
3
18. (4) The molecule in the box is (circle one):
a) i) chiral
ii) achiral
b) Rotation of the Fischer projection 90° clockwise
would:
i) retain stereochemistry
ii) change stereochemistry
CH2F
H2C=CH
CN
NH2
19. (41) In each of the following reactions reactants or products are missing. Fill in the blanks with
the appropriate molecules. If more than one step is involved, indicate this by using 1)......; 2)........
Where appropriate, draw the stereochemistry of the product(s).
a)
H3C
CH2CH2CH3
C
H3CH2C
H3C
CH3CH2SH
heat
Cl
b)
CH2CH2CH3
C
H3CH2C
H3C
+
SEt
CH2CH2CH3
C
H3CH2C
SEt
O
HgSO4
H3O+
H2
Lindlar's catalyst
c)
Cl
Cl2
H
O
1) O3
O
2) Zn / H +
d)
Cl
+
HO
KMnO4 , H3O+
+
O
vigorous conditions
e)
1) Hg(OAc)2
H2O
2) NaBH4
O
PBr3
OH
Br
1. Li
2. CuBr
3. CH 3 Br
20. (10) For each of the following pairs, circle all of the statements to their right which are
correct.
a)
CH2OH
H
OH
HO
CH2OH
and
H
H
OH
H
OH
CH2OH
CH2OH
b)
OH
H2N
HO
F
NH2
and
F
Cl
Cl
S
R
¥
¥
¥
¥
¥
mirror images
diastereomers
identical
constitutional isomers
enantiomers
¥
¥
¥
¥
¥
mirror images
diastereomers
identical
constitutional isomers
enantiomers
21. (8) Show the steps / reactants involved in the synthesis of the product shown from the given
starting material.
Cl Cl
Cl
1 eq. NaNH 2
CH 3Br
Cl
2 eq.
Cl2
CH 3
NaNH2
Br
CH3
A
22. (4) From the molecule shown, draw a Newman projection by viewing the molecule along the
central C-C bond as designated below.
H
OH H
HO
CH3
H3C
Cl
Cl
F
H
F
H
23. (2) In the molecule below, assign the hybridization of the atom indicated by the arrow.
N
sp2