Seat Assignment: _________________
Elementary Organic Chemistry - Chem 209
Final Exam
December 16, 2008
Name (print): _____________________ Name (sign): _____________________
Student Number: __________________
Multiple Choice Answers (one letter per question, 3 points each)
9. __ 10. __ 11. __ 12. __ 13. __ 14. __ 15. __ 16. __ 17. __ 18. __ 19. __ 20. __ 21. __
22. __ 23. __ 24. __ 25. __ 26. __ 27. __ 28. __ 29. __ 30. __ 31. __ 32. __
subtotal: _____________
subtotal: _____________
Total: _______________
Written Answer Questions
Written Answer Questions (points as indicated)
1.
(4 pts) Draw in the box the structure of the product of ethylation of lidocaine.
2.
(4 pts) Provide reaction conditions for the transformations shown below.
3.
(4 pts) A number of alkaloids have biological activity because of receptor binding
to an Ar-C-C-N substructure (Ar = any aromatic ring). Carefully encircle the ArC-C-N substructure buried in the structure of morphine.
1
4.
(4 pts) Give the products of reduction and then acetylation of benzyl cyanide.
5,6.
(8 pts) Using the template, sketch the 1H NMR spectrum of 1,4bis(chloromethyl)benzene. Label the H’s (a, b, etc.). Include the signal for TMS.
Sketch the integral, indicating the number of protons represented by each signal.
Hints: all the signals are singlets. Consult Table 12.2.
7.
(4 pts) Mark off the 3 isoprene units in humulene.
8.
(4 pts) What two disadvantages of soap are synthetic detergents (syndets)
designed to overcome? Please confine your answer to the box.
2
Atomic masses of the major isotope (for mass spectrometry):
H: 1
C: 12
N: 14
O: 16
Cl: 35
3
Multiple Choice Questions (3 points each)
9.
Rank the carbocations below in order of increasing stability (least stable first).
A.
B.
C.
D.
E.
10.
II < III < I
III < I < II
II < I < III
I < II < III
III < II < I
The mechanism of the reaction shown below is best described as
A.
B.
C.
D.
E.
SN 1
SN 2
E1
E2
electrophilic addition
4
11-13. To which class of natural products does each of the following belong (same
answer choice for each question)?
A.
B.
C.
D.
E.
triglycerides
phospholipids
waxes
steroids
terpenes
14-16. Choose the spectrometric method best suited to distinguish between the following
pairs of compounds (same answer choice for each question).
A.
B.
C.
D.
E.
1
H NMR
mass spectrometry
UV-visible
infrared
optical rotation
5
17.
Margarine can be made from corn oil by
A.
B.
C.
D.
E.
basic hydrolysis
acidic hydrolysis
sulfonation
catalytic hydrogenation
distillation
18.
Give the major organic product.
19.
Give the major organic product.
20.
Which of the following reacts mainly by addition (as opposed to substitution)
with Br2/FeBr3?
6
21.
Arrange the following in order of increasing basicity (least basic first).
A.
B.
C.
D.
E.
22.
What are the respective formal charges on S and N?
A.
B.
C.
D.
E.
23.
I < II < III
II < I < III
II < III < I
I < III < II
III < I < II
S
S
S
S
S
+1; N 0
-1; N +1
0; N 0
0; N +1
+1; N +1
The 1H NMR spectrum of ethyl acetate consists of (from low to high field)? Hint:
use Table 12.2
A.
B.
C.
D.
E.
singlet (3 H), singlet (2 H), triplet (3 H)
triplet (3 H), singlet (3 h), quartet (2 H)
triplet (2 H), singlet (3 H), quartet (3 H)
doublet (3 H), singlet (3 H), triplet (2 H)
quartet (2 H), singlet (3 H), triplet (3 H)
24-28. Which effect best rationalizes the following (same answer choice for each
question?
A.
B.
C.
D.
E.
resonance effect
inductive effect
molecular orbital effect
polarizability effect
solvation effect
7
24.
The greater acidity of ethanethiol (pKa 10.6) compared with ethanol (pKa 15.9)
25.
The greater acidity of trifluoroacetic acid compared with acetic acid
26.
The faster reaction of KMnO4 in benzene as an oxidizing agent in the presence of
18-crown-6 compared to oxidation without 18-crown-6
27.
The reduced basicity of N,N-dimethylaniline compared with trimethylamine
28.
The lower energy pi electronic transition of azulene compared to naphthalene
(structures below)
29-31. The following are best described as (same answer choice for each question):
A.
B.
C.
D.
E.
identical
enantiomers
diasteriomers but not epimers
epimers
not stereoisomers
29.
Lactose and maltose
30.
Cellobiose and trehalose
8
31.
Maltose and cellobiose (structures above)
32.
How many chemically different types of 1H nuclei are there in 4-heptanone?
A.
B.
C.
D.
E.
2
3
6
7
14
9