practice exam i - organic chemsitry

8/20/2019 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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practice exam i - organic chemsitry

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