Chem 133

Part II of the Preliminary Examination

November 9, 2021

Name: ___________________________________________________
A. Answer as required. Write your answer on the space provided:
1. Write the chair conformation of cyclohexane showing hydrogens in axial and equatorial position.
2. Give the staggered structural formula of hexane.
3. Write the staggered Newman projection of 2-methylbutane.
4. Identify the type of strains in 2-methylbutane and calculate the total energy cost for the type of
strain or interactions in its structure.
5. Draw the resonance structure of nitrate.
6. Calculate the formal charge of each of the atoms in carbonate.
B. Do as required.
1. Name the following compounds: (2pts each)

a. b.
H3C CH3
H H

CH3
H3C CH3

c. H3C CH3 d. H H e.

2. Draw structures corresponding to the following names: (2pts each)

a. 2. 3-Chloro-4,4-dimethyl-1-nonen-6-yne d. Trans-2,2,5,5-tetramethylhept-3-ene
b. 3,4-Dimethylcyclodecyne e.Cis-3,3-dimethyl-4-isopropylocta-1,5-
diene
c. (3E, 5Z) – 2,6- Dimethylnona-1,3,5,7-tetraene
3. Propose structure for hydrocarbon that give the following product on reaction with ozone followed by
treatment with Zn:. (3pts)
1. Poly(vinyl pyrrolidone), prepared from N-vinylpyrrolidone, is used both in cosmetics and as a synthetic
blood substitute. Draw a representative segment of the polymer. (4pts)

, N-vinylpyrrolidone
2. Show the mechanism of the following reaction by drawing curved arrows to indicate electron flow.
Then write the structure of the intermediate carbocation/s and the products formed. (5pts)

3. Show the terminal alkyne and alkyl halide from which the following product can be obtained. If two
routes look feasible, list both. (4pts)

4. Provide the reagents or structure(s) of the reactants or expected major organic product(s) generated upon
completion of the following reaction scheme: (3pts each)

a.

?
a.

b.

c.

?
d.
 ?
e.

?
f.

5. Identify the following as E or Z in all the C=C in the FORMULA. (6 points)

H3C

F
Br NH2
O
CH3
H3C
H3C
N
OH O

a. H3C O b.
6. Degree of Unsaturation.
1. Biogenic amines are derived from amino acids and act as neurotransmitters and hormones in
animals. Norepinephrine shown below affects our focus and concentration. Determine the
molecular formula and calculate the degree of unsaturation of Norepinephrine. (3 points)
OH
HO NH2

HO

2. Vitamins are important in our body. Vitamin K 1 is an anti-hemorrhagic vitamin. It is a naturally

occurring fat-soluble vitamin that is essential for the clotting of blood because of their role in the
production of prothrombin in the liver and that are used in preventing and treating
hypoprothrombinemia and hemorrhage. It is a yellow oily disubstituted naphthoquinone with a
formula of C31HXO2. Give the correct molecular formula of Vitamin K1 with a degree of
unsaturation equal to 8. (2 points)

7. Stereoisomerism.
1. D-2-deoxyribose is a sugar that constitutes DNA, a nucleic acid. Calculate the number of
stereoisomers. Draw the enantiomers and diastereomers of D-2-deoxyribose sugar. (9 points)
 2. Discuss briefly the difference and/or similarity of some properties in enantiomers,
diastereomers, meso compounds and racemic mixture. (4 points)

8. Configuration.
a. Determine the type (S or R) of configuration by showing the 2-D structure (Fischer projection)
and assigning number according to priority to each group attached on the chiral carbon center
of Valine, a crystalline essential amino acid that is one of the building blocks of plant and
animal proteins. (5 points)

b. Phenylalanine is one of the essential amino acids in humans ad is converted in the normal body
to tyrosine. Identify the indicated hydrogens in phenylalanine amino acid structure shown
below as pro-R or pro-S: ( 2 points)

9. Reaction Mechanism.
a. When isopropylidenecyclohexane is treated with strong acid at room temperature,
isomerization occurs by the mechanism shown below to yield 1-isopropylcyclohexene. Using
curved arrow, show the movement of electron involved in the bond breaking and bond
formation. 3 points

b. The dehydration of ethanol to yield water and ethylene has the following thermodynamic
parameters:
 (i) Is the reaction exothermic or endothermic? 1 point
(ii) Is the reaction favorable (spontaneous) or unfavorable (nonspontaneous) at room
temperature (298 K)? 2 points

10. Draw the structure of the following molecules:

a. 2-chloro-3-fluoro-4-methylpentane

b. o-chlorotoluene

c. trans-2,3-dicholoro-but-2-ene

11. Name the following:

a. b. c. d.

e. f. g.

12. Use curved arrows to show the mechanism. Give the products. Determine the type of
mechanism.

HO
CH3 SOCl2
H3C
a. CH3 __________
b.

c.

13. Complete the following equations:

NaSH
a. H3C CH2CH2 Br ____________

b.

c.

Ag2O, H2O
d. →

e.

f.

g.
14. Choose the type of reaction mechanism (SN1, SN2, E1, E1cB, and E2) or identify the
reactant(s) required so the reaction will occur in the following reaction conditions.
The primary alkyl halide (RCH2X) reacts by an:
(5.1)_____ if a strong base is used (OH-, OR-)
(5.2) _____ if a good nucleophile is used
(5.3) ______ if the leaving group is two carbons away from a carbonyl group (HO-C-C-C=O)
The secondary alkyl halide (R2CHX) reacts by
SN2 if a weakly basic (5.4) ____________ is used E2 if a (5.5) ______________ is used.
The tertiary alkyl halide (R3CX) reacts by an
Mixture of (5.6) ______ and (5.7) ______ pathways under neutral or acidic condition
(5.8) ______ if a strong base is used

15. Which ion in each of the following pairs is a better leaving group?
(a) F- or Br - (b) Cl- or NH2- (c) OH- or I-

16. Which alkyl halide in each of the following pairs will react faster in an SN2 reaction with OH-?
(a) Bromobenzene or benzyl bromide, C6H5CH2Br
(b) CH3Cl or (CH3)3CCl
(c) CH3CHPCHBr or H2CPCHCH2Br

17.

18. Calculate the oxidation level of the following:

a. CH3(C=O)CH(Cl)COOH
b. CH2(Br)CH(OH)CH3