ORGANIC CHEMISTRY I – PRACTICE EXERCISE Alkene reactions ...
ORGANIC CHEMISTRY I ¨C PRACTICE EXERCISE
Alkene reactions and mechanisms
FOR QUESTIONS 1-24, GIVE THE MAJOR ORGANIC PRODUCT OF THE REACTION,
PAYING PARTICULAR ATTENTION TO REGIO- AND STEREOCHEMICAL OUTCOMES.
1)
O
HCl
CH3OH
2)
CH3
HCl
3)
HCl
4)
HCl
5)
HBr
6)
HCl
7)
CH3
H3O
+
8)
H3O
+
9)
H3O
+
10)
CH3
Hg(OAc)2, H2O
NaBH4
11)
Hg(OAc)2, H2O
NaBH4
12)
Hg(OAc)2, CH3OH
13)
CH3
BH3
H2O2
THF
OH
-
14)
(Z)-3-hexene
1) BH3 / THF
-
?
2) H2O2 / OH
15)
H2
Pt
16)
CH3
Br2
CH2Cl2 (solvent)
17)
Cl2
CH2Cl2 (solvent)
18)
Cl2
H2O
19)
CH3
1) CH3CO3H
+
2) H3O
20)
PhCO3H
CH2Cl2 (solvent)
21)
CH3
OsO4
H2O2
22)
CH3
1) O3
2) (CH3)2S
23)
KMnO4
(hot, conc.)
NaBH4
24)
1) O3
2) (CH3)2S
25) Treatment of cyclopentene with peroxybenzoic acid
A) results in oxidative cleavage of the ring to produce an acyclic compound
B) yields a meso epoxide
C) yields an equimolar mixture of enantiomeric epoxides
D) gives the same product as treatment of cyclopentene with OsO4
E) none of the above
26) Provide a detailed, step-by-step mechanism for the reaction shown below.
Br2
HO
+
O
HBr
Br
27) Provide a detailed, step-by-step mechanism for the reaction shown below.
+
H3O
HO
O
28) Provide the reagents necessary to complete the following transformation. The synthesis may involve
more than one step.
Br
OH
?
OH
29) Provide the reagents necessary to complete the following transformation. The synthesis may involve
more than one step.
Br
?
OH
+
enantiomer
OH
30) Provide the reagents necessary to convert 3-methyl-2-butanol to 2-methyl-2-butanol. The synthesis
may involve more than one step.
31) Both (E)- and (Z)-hex-3-ene are subjected to a hydroboration-oxidation sequence. How are the
products from these two reactions related to each other?
A) The (E)- and (Z)-isomers generate the same products but in differing amounts.
B) The (E)- and (Z)-isomers generate the same products in exactly the same amounts.
C) The products of the two isomers are related as constitutional isomers.
D) The products of the two isomers are related as diastereomers.
E) The products of the two isomers are not structurally related.
32) What alkene would yield the following products upon ozonolysis?
CH3CH2CH2CH2CHO + CH2O
33) Addition of Br2 to (E)-hex-3-ene produces
A) a meso dibromide
B) a mixture of enantiomeric dibromides which is optically active
C) a mixture of enantiomeric dibromides which is optically inactive
D) (Z)-3,4-dibromo-3-hexene
E) (E)-3,4-dibromo-3-hexene
34) The mechanism for the acid-catalyzed hydration of alkenes is the reverse of the acid-catalyzed
dehydration of alcohols. This illustrates the principle of _______________________.
35) Which of the following is the best reaction sequence to accomplish a Markovnikov addition of water to
an alkene with minimal skeletal rearrangement?
A) water + dilute acid
B) water + concentrated acid
C) oxymercuration-demercuration
D) hydroboration-oxidation
E) none of the above
36) Which of the following additions to alkenes occur(s) specifically in an anti fashion?
A) hydroboration-oxidation
B) addition of Br2
C) addition of H2
D) addition of H2O in dilute acid
E) both A and B
37) Which of the following additions to alkenes occur(s) specifically in an syn fashion?
A) dihydroxylation using OsO4, H2O2
B) addition of H2
C) hydroboration
D) addition of HCl
E) A, B, and C
38) HBr can be added to an alkene in the presence of peroxides (ROOR). What function does the peroxide
serve in this reaction?
A) nucleophile
B) electrophile
C) radical chain initiator
D) acid catalyst
E) solvent
ANSWERS
1)
OH
+
OCH3
2)
CH3
Cl
3)
Cl
4)
Cl
5)
Br
6)
Cl
7)
OH
CH3
8)
OH
9)
OH
10)
HO
CH3
enantiomer
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