Download - Practice Exam I - Organic Chemsitry
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Practice Exam I
CHEM 2322
1. In an addition reaction to an alkene, the π bond plays the role o!"# n$cleophile
%# electrophile
C# lea&in' 'ro$p
(# " and %
E# % and C
2. )hich statement best describes the temperat$re dependence o an addition reaction*
"# "ddition reactions are thermodynamically a&ored at all temperat$res.
%# "ddition reactions are thermodynamically disa&ored at all temperat$res.
C# "ddition reactions are thermodynamically a&ored at lo+ temperat$res.
(# "ddition reactions are thermodynamically a&ored at hi'h temperat$res.
E# "ddition reactions are thermodynamically impossible.
3. )hich o the str$ct$res sho+n depicts the most stable carbocation intermediate ormed in
the hydrohalo'enation reaction sho+n*
"# I
%# II
C# III
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(# I
E#
-. )hich o the 'i&en reaction schemes +o$ld prod$ce the molec$le sho+n belo+*
"#
%#
C#
(# %oth " and %
E# %oth % and C
. )hat +o$ld be the optimal conditions to eect the ollo+in' transormation*
"# (il$te H2/0-
%# Concentrated H2/0-
C# (il$te H%r
(# Concentrated H%r
. )hat is the expected major prod$ct or the ollo+in' reaction*
"#
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%#
C#
(#
E#
. )hat is the name o the prod$ct ormed +hen chloro1methylcyclohexene is red$ced
+ith a Pt catalyst and H2*
"# 1chloro2methylcyclohexane
%# 1chloro3methylcyclohexane
C# 1chloromethylcyclohexane
(# 3chloro1methylcyclohexane
E# 4one o the abo&e
5. )hich reaction intermediate is ormed +hen -methylcyclohexene reacts +ith %r 2dissol&ed in CCl-*
"# I
%# II
C# III
(# I
E#
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6. )hat is the expected major prod$ct or the ollo+in' reaction*
"# I
%# II
C# III
(# I
E#
17. )hat are the major prod$cts or the ollo+in' reaction se8$ence*
"# I and II
%# II and III
C# III and I
(# I and III
E# II and I
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11. )hich o the ollo+in' alkene addition reactions occ$r9s# speciically in syn ashion*
"# dihydroxylation $sin' 0s0-, H202
%# addition o H2
C# hydroboration(# addition o HCl
E# ", %, and C
12. Pro&ide the expected major or'anic prod$ct o the reaction se8$ence sho+n.
"# I and II
%# I and C# I only
(# II only
E# III only
13. )hich reaction is not stereospeciic*
"# I
%# II
C# III
(# I
1-. :or the reaction se8$ence sho+n, +hat is the expected major prod$ct*
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"# I
%# II
C# III
(# I
E#
1. )hat is the I;P"C name or the molec$le sho+n belo+*
"# bromo3octyne
%# bromomethyl3heptyne
C# 2bromo2methyl-heptyne
(# bromo,dimethyl3hexyne
E# 2bromo-octyne
1. )hich o the ollo+in' is a str$ct$re or hepta3,dien1yne*
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I I I I I I I , ,
"# I
%# II
C# III
(# I
E#
"ns! "
1.
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"# I
%# II
C# III
(# I
E#
27. :or the reaction sho+n, select the expected ma>or or'anic prod$ct.
"# I
%# II
C# III
(# I
E#
21. /elect the best rea'ent to con&ert 3heptyne to trans3heptene*
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"# 4a?4H3
%# 1 e8. 4a4H2, 4H3
C# xs 4a4H2, 4H3
(# H2?PtE# H2?@indlarAs catalyst
22. )hich rea'ents sho+n belo+ +o$ld be expected to con&ert 2pentyne to (Z)2pentene*
"# H2, Pt
%# 4a, 4H3
C# H2, @indlarAs catalyst
(# excess HCl
E# H'/0-, H20
23. )hich o the compo$nds sho+n belo+ +o$ld be the most likely prod$ct expected rom the
reaction scheme sho+n*
"# I
%# II
C# III(# I
E#
2-. :or the transormation sho+n, select the most appropriate rea'ent9s# to eect the chan'e.
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"# H2/0-, H'/0-, H20
%# 1. (isiamylborane, 2. H0 B , H202
C# 2Cr 20, HD
(# 4a0ClE# H2, Pd
2. :or the reaction sho+n, +hich o the compo$nds listed +o$ld be the expected ma>or, and
inal, or'anic prod$ct*
"# I
%# II
C# III(# I
E#
2. In an acidcatalyed hydration, +hich o the ollo+in' alkynes is expected to prod$ce a
sin'le ketone*
"# 2decyne
%# 3decyne
C# -decyne
(# decyne
E# "ll o the abo&e +ill 'i&e a sin'le prod$ct
2. Predict the major or'anic prod$cts o the reaction belo+.
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"# I and II
%# II and IIIC# I and I
(# II and III
E# 1 and III
25. )hat is the expected major prod$ct o the reaction se8$ence sho+n belo+*
"# I
%# II
C# III(# I
E#
26. )hich o the ollo+in' is the most stable radical*
%
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37. In the molec$le sho+n belo+, determine +hich o the hi'hli'hted CH bonds 9rom a toe# is expected to ha&e the lo+est bond dissociation ener'y.
"# CHa
%# CH b
C# CHc
(# CHd
E# CHe
31. )hich term most acc$rately describes the process sho+n belo+*
% r D H % r D
"# co$plin'%# proton transer
C# halo'en abstraction(# hydro'en abstraction
E# homolytic clea&a'e
32. )hich o the ollo+in' is an example o termination*
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C
33. )hich o the ollo+in' is most reacti&e to+ards chlorination*
"# methane
%# chloromethane
C# dichloromethane
(# chloroorm
E# ethane
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