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Practice Exam-Il
Name Tona+h~() {aslallo(Last) (First)
Student #--------------------This exam is divided up into two
parts, multiple choice and short answer questions. All workmust be
shown in order to receive full credit. Please turn off all
electronic communicationdevices.
Multiple choice questions: Choose the correct answer and record
it on the scantron provided.(2 points each)
1. What is the IUPAC name of the following compound?
IUV l {;~ 1;4- hCf.hql/en(F 3 r 3 - e-f-hy I
5 - m-efhy/C J.."I
AE)-3-methyl-5-vinyl-3-heptene (I:)- 3- efA l : 5... .U I-I /1 h
1.-1'Y(Z)-1,3-diethyl-l-methyl-l,4-pentadiene Y tr'Jrtr/1y / '1 -
cyJ/l'LPI I file
c. (Z)-3-ethyl-5-methyl-l,4-heptadiene@
(E)-3-ethyl-5-methyl-l,4-heptadiene
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2. Which of the following compounds does not have an index of
hydrogen deficiency of 5?o
a b c
3. Assign the compounds (in the order I to II) as Z or EH3C
@>Z,Z (b)Z,E ~,E
4. Which of the following concepts explains Markovnikov's rule
as applied to the addition ofHBr to propene?
~ the Aufbau principle~). the acidity of HBr
~Jt_~'(b). the nucleophilicity of bromide anion@. the relative
stability of carbocations
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5. Which of the following has the highest value of Amax in the
ultraviolet-visible spectrum?
a b c @6. What is the major organic product obtained from the
following reaction?
~
~()t1
7. What is the best choice ofreagent(s) to perform the following
transformation?
+4~~oOH OH
~a c
2. NaBH4
o
? •
(a). OS04; followed by NaHS03(c). BH3; followed by H202,
NaOH
o(b). Hg(OAchandH~; followed byNaB~@ 03; followed by Zn!acetic
acid.
8. Which of the following reactions of alkenes takes place with
anti stereospecificity?
k4dihYdroXYlation (treatment with OS04 followed by NaHS03) o/nM.
hydrogenation (treatment with H2/Pt) 5yn~. addition ofHBr
(treatment with HBr) f"tl{em/x.®. bromination (treatment with
Brz)
9. What is the major organic product obtained from the following
reaction? Chat· 7-7 ;!1el'Cury-tZi,+1t Iyzdo f.fytJ.ltff1/J1I
~ ---=c.--HU C""" •• oOH~cUd
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10. What is the major organic product obtained from the
following reaction?
b••
Lindlar Pd
~~ c d11. What type of reactive intermediate is formed in the
reaction of an alkene with Br2 and water
to give a bromohydrin? . d1(a) carbocation (b) carbanion (c)
radical 2 > 3
2 3(b) 1> 3 > 2 @3>2>1 (d) 2 > 3> 1
14. Which of the following can exist as cis/trans isomers?
#;:t(a) \=::(/1/
(d)
(c)
t/
H
15. Which of the following concepts can be used to explain the
order of carbocation stability(3°>2°>1°)(a) electronegativity
(b) resonance @ Inductive effect (d) octet rule
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Short answer Questions
1. Write the complete stepwise mechanism for the following
reaction. Show all intermediatestructures and electron flow with
arrows (10 points).
2. What product would you expect from the reaction of
cyclopentene with NBS and water?What is the stereochemistry of the
product formed. Explain the formation of this product bydrawing a
detailed reaction mechanism (12 points).
Brf8rl' _
\ (
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3. Add curved arrows in the following reactions to show the flow
of the electrons (12 points)
(a)
:'O:e
(b)
H e
•
o·••• ~MgBr
(c) •
(d).. r\H-UH + H3V-MgBr + e ~HO: MgBr
••
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4. Give the structure of the principal organic product(s) in the
following reactions indicatingboth regiochemistry and
stereochemistry when appropriate (16 points)?
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
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5. Some of the following compounds can exhibit geometric (E/Z)
isomerism, and some cannot.Indicate which ones can and cannot show
E/Z isomerism. Draw the structures of thesecompounds including E
and Z isomers (12 points):
(a) 3-bromo-2-cWoro-2-pentene(b) 3-bromo-2-methyl-2-butene(c)
4-t-butyl-5-methyl-4-octene
c) 4v..u.
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6. What combination of diene and dienophile undergoes
Diels-Alder reaction to give each ofthe following adducts (8
points)?
CfJOCH-;{!ftrN"}
d:~t;{
COOCH3~COOCH3
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