Download CHEMISTRY 211 FINAL EXAM Wed., December 4, 2002 Name

CHEMISTRY 211
FINAL EXAM
.
Name
Wed., December 4, 2002
Hold
Answer all questions (150 pts).
1. (10) Name the following molecules using IUPAC rules. Where appropriate, assign E or Z
designations.
a)
b)
Cl
Br
2. (3) What is the IUPAC name of the compound shown below?
a)
b)
c)
d)
Nonane
2,3,5-trimethylhexane
2,6-dimethylheptane
1,1,2,4,4-pentamethylbutane
(CH3)2CHCH(CH3 )CH2CH(CH3 )2
3. (3) How many secondary carbon atoms are present in the molecule shown?
a)
b)
c)
d)
zero
one
two
five
(CH3)3CCH2 CH2 CH(CH3)2
4. (3) How many different monochloro derivatives are possible for the molecule shown?
a) three
b) four
c) five
d) six
5. (3) What compound (a-d) is represented by the Newman projection shown?
.
a) CH 3CH2CH 3
b) (CH3) 2CHCH 2CH3
c) CH 3CH(CH3) 2
d) CH3CH 2CH2 CH(CH3)2
H3 C
H
H
H
CH3
CH2 CH3
6. (3) Which of the following describes the most stable conformer of cis-1-tert-butyl-2methylcyclohexane?
a)
b)
c)
d)
The tert-butyl group is equatorial and the methyl group is axial
The tert-butyl group is axial and the methyl group is equatorial
Both groups are equatorial
Both groups are axial
7. (3) The degree of unsaturation (rings and/or multiple bonds) for the formula
C7H4Cl2N2O4 is:
a) 4
b) 5
c) 6
d) 7
8. (3) What is the relationship between these structures?
a) constitutional isomers
b) same compound
c) enantiomers
d) diastereomers
H3 C
H
C
H3 C
C
Cl
H
C
CH3
C
Cl
H3 C
9. (6) Circle any of the following which are chiral.
a)
b)
NH2
H
H
F
CH2OH
c)
Br
Br
H
OH
H
OH
HO
H
HO
H
d)
H3C
H
SH
COOH
CH2OH
10. (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)
CH3
H
O
+
NaCN
H
b)
+
LiSH
c)
NH
+
H-Br
11. (3) If a molecule has 7 stereogenic centers and 2 of the possible stereoisomers are meso, there
will be how many stereoisomers in total?
a)
27
b)
72 - 2
27 - 2
c)
d) 22 - 7
e)
27-2
12. (3) Which of the following is the major organic product of the reaction shown?
1. BH3
2. H2O2, -OH
a) HO
H
CH3 b)
H
CH3
H
OH
H
c)
H
CH3 d) HO
CH3
H
OH
OH
H
13. (2.5) True or False? The pKa of a proton attached to the C of a terminal alkyne is more acidic
than that in NH3.
14. (2.5) True or False? An achiral molecule must have a superimposable mirror image.
15. (4.5) For the following, circle all of the statements to the right which are correct.
1 equivalent Br2
anti addition
syn addition
halogenation
hydration
substitution
Markovnikov addition
Br
Br
16. (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)
Cl
b)
BrCH2
NH
H2N
CN
NC
17. (3) Which carbocation would you predict to be the least stable?
+
CHCH2
CH3 CH
CH3
CH2 CH2
CH3 CHCHCH 3
+
B
A
+
C
CH3
CH3 CH2 CCH 3
+
D
18. (9) The Molecule (A), shown below, reacted with NaCN in acetone as solvent to yield a single
product (B) {optical rotation +20°}. However, treatment of (A) with CH3OH gave 2 products, (C)
and (D) {optical rotations +37° and -37°, respectively}. Draw products (B), (C) and (D) and explain
briefly, but clearly, what type of reaction is taking place in each case and why this would lead to the
outcome described.
Br
H
(A)
19. (3) Which Fischer projection is the same as the molecule in the box?
NH2
COOH
NH2
CH 3
NH 2
C
NH2
H
HOOC
CH3
CH3
COOH
H
COOH
CH3
H
H
(A)
(B)
20 (3) The molecule in the box has what configuration?
(A) R (B) S
(C)
CH2OH
H 3C
COOH
OH
21. (40) 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)........ If
more than one product could be formed, show only the major product(s). Where appropriate, draw
the stereochemistry of the product(s).
a)
OH
Cl
b)
O
H2
Pd
c)
HO
OH
H
HBr
KMnO4
H3O+
heat
d)
NBS
light
22. (7.5) For each of the following pairs, circle all of the statements to their right which are
correct.
a)
OH
H2N
Cl
and
CHO
HO
HO
HO
Cl
H3C
CH3
b)
HO
NH2
CHO
HO
OH
CH2OH
mirror images
diastereomers
identical
constitutional isomers
enantiomers
mirror images
diastereomers
identical
constitutional isomers
enantiomers
23. (8) Show the steps / reactants involved in the synthesis of the product shown from the given
starting material.
O
24. (5) From the molecule shown, draw a Newmann projection by viewing the molecule along the
central C-C bond as designated below.
OH
H
Cl
H
A
H 3C
F
25. (2) In the molecule below, assign the hybridization of the atom indicated by the arrow.
C
C
O