Chapter 7

7.1 One problem with elimination reactions is that mixtures of products are often formed. For example,
treatment of 2-bromo-2-methylbutane with KOH in ethanol yields a mixture of two alkene products.
What are their likely structures?
Solution:

major product
Br

7.2 How many alkene products, including E,Z isomers, might be obtained by dehydration of
3-methyl-3-hexanol (3-methyl-3-hydroxyhexane) with aqueous sulfuric acid?
Solution:

dehydration

OH

7.3 What product would you expect to obtain from addition of Cl2 to 1,2-dimethylcyclohexene? Show
the stereochemistry of the product.
Solution:
 Cl

CH3
Cl

H3C CH3
H3C CH3 Cl
H3 C Cl

Cl Cl
Cl

H3C Cl
H3C CH3
Cl
Cl CH3

7.4 Addition of HCl to 1,2-dimethylcyclohexene yields a mixture of two products. Show the
stereochemistry of each, and explain why a mixture is formed.
Solution:
Cl

Cl

CH3
H3C CH3 H3C
H3 C CH3
H Cl

CH3
CH3
H3C
Cl
H3 C Cl

7.5 What product would you expect from the reaction of cyclopentene with NBS and water? Show the
stereochemistry.
Solution:
 H OH
H
O
H H OH
Br Br
H Br

H Br

Br
H Br
H

Br

H OH
H OH

7.6 When an unsymmetrical alkene such as propene is treated with NBS in aqueous DMSO, the major
product has the bromine atom bonded to the less highly substituted carbon atom. Is this
Markovnikov or non-Markovnikov orientation? Explain.
OH

NBS,H2O
H3C C CH2 H3C C CH2Br
H DMSO H
Solution:

Br
Br H
H
vs
H3C CH2
H3C CH2

H 2O
H 2O
The product is Markovnikoff product.

7.7 What products would you expect from oxymercuration of the following alkenes?
Solution:
(a)

H2 H2 Hg(OAc)2 H2 H2 H
H3C C C C CH2 H3C C C C CH3
H H2O
OH
2-pentanol
(b)
OH
H2 Hg(OAc)2 H2 H2
H3C C C C CH3 H3C C C C CH3
H H2O
CH3 CH3
2-methyl-2-pentanol
7.8 What alkanes might the following alcohols have been prepared from?
Solution:
(a)
H2 H2
H3C C C C C CH3
H Hg(OAc)2
OH
CH3
H2O H2 H2 H2
2-methyl-2-hexene H3C C C C C CH3

Hg(OAc)2
OH
H2 H2 H2 H2O
H2C C C C C CH3

CH3
2-methyl-1-hexene
(b)

OH
Hg(OAc)2

H2O

cyclohexylethylene
1.BH3

-
2.H2O2 OH

ethylidenecyclohexane

7.9 Show the structures of the products you would obtain by hydroboration/oxidation of the following
alkenes:
CH3
(a) (b) CH3
CH3C CHCH2CH3

CH3 OH
Solution: (a)
CH3CH CHCH2CH3

OH
(b)

CH3

7.10 What alkenes might be used to prepare the following alcohols by hydroboration/oxidation?
(a) (CH3)2CHCH2CH2OH
 OH
(b)
(CH3)2CHCHCH3

(c)
CH2OH

Solution: (a) (CH3)2CHCH CH2

(b) (CH3 )2C CHCH3
(c)
CH2

7.11 The following cycloalkene gives a mixture of two alcohols on hydroborotion followed by
oxidation, Draw the structures of both, and explain the result.
H
H3C

CH3
H
Solution:
The structure of the two cycloalcohols:
H

H3C
OH CH3

H
H
H3C 1. BH3 / THF H

2. OH-, H2O OH
CH3
H
H3C
H H

CH3
H

7.12 What products would you expect from the following reactions?
CH2
Cl KOH
(a) ?
Cl C Cl
H

Zn(Cu)
(H3C)2HCH2CHC CHCH3 CH2I2 ?
(b)

Solution:
 CH2 Cl Cl
Cl KOH
C
(a)
Cl C Cl HCl

Zn(Cu)
(b) (H3C)2HCH2CHC CHCH3 CH2I2 ZnI2

7.13 What product would you obtain from calalytic hydrogenation of the following alkenes?
CH3
H2
(a) H3C C C C CH3
H
CH3
(b)

CH3
Solution：
CH3
H2 H2
(a) H3C C C C CH3
H
CH3
(b)

CH3

7.14 What alkene would you start with to prepare each of the following compounds?
H
OH OH OH OH OH
(a) H2 H2 H2
(b) (c) HO
H3C C C C CH3 C C C C OH
H H H

CH3
OH
CH3 S
olution:
H

(a) H2
(b) (c)
H3C C C C CH3 H2C C C CH2
H H H

CH3

CH3

7.15 What products would you expect?

Solution:
(a) Aqueous acidic KMnO4
Product CH3COCH2CH2CH2CH2COOH
 (b) O3
Product CH3COCH2CH2CH2CH2CHO

7.16 Propose structure for alkenes.

Solution:
(a): (CH3) 2C=O and H2C=O
Structure (CH3) 2C =CH2
(b): 2 equiv CH3CH2CH=O
Structure CH3CH2CH=CHCH2CH3

7.17 Show the monomer units you would use to prepare the following polymers:

OCH3 OCH3 OCH3

H2 H2 H2
C C C C C C
H H H

(a)
OCH3

Solution: The monomer unit is H2C CH .

Cl Cl Cl Cl Cl Cl

C C C C C C
H H H H H H

(b)
Solution: The monomer unit is ClHC CHCl.

7.18 One of the chain-termination steps that sometimes occurs to interrupt polymerization is the
following reaction between two radicals:

2 CH2CH2 CH2CH3 + C CH2

H
Propose a mechanism for this reaction, using fishhook arrows to indicate electron flow.
Solution:

H
C CH2

H C CH2 + CH2CH3
H

H2
C CH2

7.19 tert-Butyl vinyl ether is polymerized commercially for use in adhesives by a cationic process.
Draw a segment of poly(tert-butyl vinyl ether), and show the mechanism of the chain-carrying step.

tert-butyl vinyl ether

Solution:

Acid catalyst
O
H

O
O O
O

Repeat many times O

H2
* C C *
H n

7.20 Name the following alkenes, and predict the products of their reaction with (i) KMnO4 in aqueous
acid and (ii) O3, following by Zn in acetic acid:

(a) (b)
Solution: (a)2,5-dimethyl-2-heptene
O

OH
and
(i)
O

H
and
(ii)
(b)3,3-dimethylcyclopentene
 HO O
OH

(i) O

H O
H

(ii) O

7.21 Draw the structures of alkenes that would yield the following alcohols on hydration (red=O). Tell
in each case whether you would use hydroboration/oxidation.

Solution: (a) CH2

I would use oxymercuration in this case.

(b)
Both oxymercuration / demercuration and hyboration / oxidation reactions could be used.

7.22 The following alkene undergoes hydroboration/oxidation to yiele a single product rather than a
mixture. Explain the result, and draw the product showing its stereochemistry.
Solution: The reactant is symmetrical, so OH adding to either of the carbon that is double bonded

will yield the same product. The single product is: OH

7.23 Predict the products of the following reactions (the aromatic ring is unreactive in all cases).
Indicate regiochemistry when relevant.
(a) H2/Pd
Br2
(b)
CH CH2
(c) HBr
1.OsO4
(d)
2.NaHSO4
(e) D2/Pd
 H H
CH CH2 H C C H
H2/Pd H

Solution: (a)
H H
Br C C Br
CH CH2
H
Br2

(b)
H H
Br C C
CH CH2
H
HBr H

(c)
HO OH
H H
CH CH2 C C
1.OsO4 H
2.NaHSO4
(d)
D D
H H
CH CH2 C C
D2/Pd H

(e)

7.24 Suggest structures for alkenes that give the following reactions products. There may be more than
one answer for some cases.
CH3
CH3 CH3
?
(a) ? CH3CHCH2CH2CH2CH3 (b)
Br CH3 Cl
Br 2 HCl
? CH3CHCHCH2CHCH3 ? CH3CHCHCH2 CH2CH2CH3

(c) Br (d) CH3

OH
1.Hg(OAc)2,H2O
? CH3CH2CH2CHCH3
(e) 2.NaBH4
CH3CHCH2CH2CH CH2 H3C

Solution: (a) CH3 H3CHCH2CHC CHCH3

H3C CH3
H3CHCHC CHCH2CH3 H3CC CHCH2CH2CH3
CH3
H2C CCH2CH2CH2CH3
CH3 CH3
CH3 CH3

(b)
CH3

(c) H3CHC CHCH2 CHCH3

 H2C CHCHCH2CH2CH2CH3

(d) CH3
(e) H3CH2CH2CHC CH2

7.25 Predict the products of the following reactions, indicating both regiochemistry and
stereiochemistry when appropriate:
CH3
1. O3
?
2.Zn, H3O+
(a) H
O
CH3
CH3
1. O3
2.Zn, H3O+
H
H
Solution: O

KMnO4
?
H3 O+
(b)
O

OH
KMnO4
H3O+
OH

Solution: O

CH3

1. BH3
?
2. H2O2,- OH
(c)
CH3 H CH3 CH3 H
1. BH3
+
2. H2O2,- OH

OH H H OH

Solution: 50% 50%

CH3
1. Hg(OAc)2,H2 O
?
2. NaBH4
(d)
 CH3 OH
H CH3 H
1. Hg(OAc)2,H2O
2. NaBH4

H OH H CH3

50%
Solution: 50%

7.26 How would you carry out the following transformations? Indicate the reagents you would use in
each case.
H

OH
?
OH

(a) H

OH
1.OsO4
2.NaHSO3 ,H2O OH

Solution: H

OH

(b)
OH

1. Hg(Ac)2
2. NaBH4
Solution:
H
Cl

?
Cl
(c) H
H
Cl
1. CHCl3
2. KOH
Cl
Solution: H
CH3
CH3

OH ?

(d)
 CH3
CH3

OH 1. H2SO4, H2 O
2. THF, 50 ℃
Solution:
CH3 O CH3

? CH3CH + CH3CHCH
H3CHC CHCHCH3

(e) O
CH3 O CH3

H3CHC CHCHCH3
1. O3
CH3CH + CH3 CHCH
2. Zn/H3 O+
Solution: O

CH3 CH3

?
(f) H3CC CH2 CH3CHCH2 OH

CH3 CH3

1. BH3 , THF
H3CC CH2 CH3 CHCH2OH
Solution: 2. H2O2,OH-

7.27 What product will result from hydroboration/oxidation of 1-methylcyclopentene with deuterated
borane, BD3? Show both the stereochemistry (spatial arrangement) and the regiochemistry
(orientation) of the product.
H CH3
H CH3 H CH3
δ -
OH
H2O2
D B
δ D
D2B D HO D
D
BD3
H CH3 D
D
D B
D2B D HO D
-
OH
δ δ H2O2
H CH3
H CH3 H CH3

7.28 Draw the structure of an alkene that yield only acetone, (CH3)2C=O, on ozonolysis followed by
treatment with Zn.

O3
O + O
Zn/H3O+

7.29 Draw the structure of a hydrocarbon that react with 1 molar equivalent of H2 on catalytic
hydrogenation and gives only pentanal , CH3CH2CH2CH2CHO, on the ozonolysis followed by
treatment with Zn. Write the reaction involved.
Solution:
The structure of the hydrocarbon is showed in the following picture:

The reactions are showed as follow:

Catalyst

H2
O3
H
2
Zn/H3O
O

7.30 Draw the structure of alkenes that give the following products on oxidative cleavage with KMnO4
in the acidic solution:
O O O
+
+ CO2
(a). (b).
O

O +

(c).
Solution:

(a). (b).

(c).

7.31 Compound A has the formula C10H16. On catalytic hydrogenation over palladium, it reacts with
only 1 molar equivalent of H2. Compound A also undergoes reaction with ozone, followed by zinc
treatment, to yield a symmetrical diketone, B (C10H16O2).
(a) How many rings does A have?
A have two rings.
(b) What are the structures of A and B?
 A

O
(c) Write the reactions.

+H2 palladium

Zn
+O3

O
7.32 An unknown hydrocarbon A, with formula C6H12, reacts with 1molar equivalent of H2 over a
palladium catalyst. Hydrocarbon A also reacts with OsO4 to give a diol, B. When oxidized with
KMnO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2CO2H,
and the other fragment is a ketone. C. What are the structures of A, B, and C? Write all reactions,
and show your reasoning.

H2
C CH3
B H3C
H CH3
HO OH
O

C
 palladium
+ H2

H2
C CH3
OsO4 H3C

H CH3
HO OH
O
O
KMnO4
+ H3C C H
C O
H2

7.33 Using an oxidative cleavage reaction explain how you would distinguish between the following
two isomeric dienes:

and
Solution: When they react with KMnO4 in acid, the first one will yield two products and the second one
will only yield one product.

7.34 Compound A, C10H18O, undergoes reaction with dilute H2SO4 at 2500C to yield a mixture of two
alkenes, C10H16. The major alkene product, B, gives only cyclopentanone after ozone treatment
followed by reduction with zine in acetic acid. Identify A and B, and write the reaction.
Solution: A: B:
HO

Reaction:
HO
H2SO4

2500C
major

O3
O
Zn/H3O

7.35 Which reaction would you expect to be faster, addition of HBr to cyclohexene or to
1-methylcyclohexene? Explain.
Solution: The intermediates of the two reactions are not equal in stability. Judge by Hammond postulate,
the more stable intermediate forms faster, so addition of HBr to 1-methylcyclohexene may be
faster.
7.36 Predict the products of the following reactions, and indicate regiochemistry if relevant:
Br
(a) HBr

(c)
CH2I2 , Zn-Cu
H H

(d)
CH2I2 , Zn-Cu
H
H

7.37 Iodine azide, IN3, adds to alkenes by an electrophilic mechanism similar to that of bromine. If a
monosubstituted alkene such as 1-butene is used, only one product results:

N N N

H3CH2CHC CH2 + I N N N CH3CH2CHCH2 I

(a) Add lone-pair electrons to the structure shown for IN3, and draw a second resonance form for the
molecule.

I N N N I N N N

(b) Calculate formal charges for the atoms in both resonance structures you drew for IN3 in part
For the iodine:
Iodine valence electrons =7
Iodine bonding electrons =2
Iodine nonbonding electrons =6
Formal charge = 7 - 2/2 – 6 = 0
For the left nitrogen:
Nitrogen valence electrons =5
Nitrogen bonding electrons =6
Nitrogen nonbonding electrons =2
Formal charge = 5 – 6/2 – 2 = 0
For the middle nitrogen:
Nitrogen valence electrons =5
Nitrogen bonding electrons =8
 Nitrogen nonbonding electrons =0
Formal charge = 5 – 8/2 – 0= 1
For the right nitrogen:
Nitrogen valence electrons =5
Nitrogen bonding electrons =4
Nitrogen nonbonding electrons =4
Formal charge = 5 – 4/2 – 4= - 1

(c) In light of the result observed when IN3 adds to 1-butebe, what is the polarity of the I-N3bomd?
Propose a mechanism for the reaction using curved arrows to show the electron flow in each step.

H3CH2CHC CH2 + I N N N

N N N
H3CH2CHC CH2I N N N
CH3CH2CHCH2I

7.38 Draw the structure of a hydrocarbon that absorbs 2 molar equivalents of H2 on catalytic
hydrogenation and gives only butanedial on ozonolysis.
O O
H2 H2
HC C C CH Butanedial

Solution:

7.39 Simmons–Smith reaction of cyclohexene with diiodomethane gives a single cycloproprane

product, but the analogous reaction of cyclohexene with 1,1-diiodoethane gives (in low yield) a
mixture of two isomeric methylcyclopropane products. What are the two products, and how do
they differ?
Solution: The reaction occurs as below:

H H3C
CH3 H
Zn(Cu)
+ I2HC CH3
Ether +

7.40 In planning the synthesis of one compound from another, it’s just as important to know what not to
do as to know what to do. The reactions all have serious drawbacks to them. Explain the potential
problems of each.
Solution:
(a)
 CH3 CH3
HI
H3C C CHCH3 H3 C C CHCH3
H
I
According to Markovnikov’s rule the reaction should be:
CH3 CH3
HI
H3C C CHCH3 H3C C CH2CH3
I
(b)
H
OH
1.OsO4
2.NaHSO3 H
OH
Actually it should be syn addition as below:
H
OH
1.OsO4
2.NaHSO3
OH
H
(c)

1.O3 CHO
2.Zn CHO
Actually the reaction should be:
H2
1.O3 2 OHC C CHO
2.Zn
(d)
H
CH3 CH3
1.BH3
2.H2O2 , OH OH
H
Actually the reaction should be:
H
CH3 CH3
1.BH3
2.H2 O2, OH H
OH
7.41 Which of the following alcohols could be made selectively by hydroboration/oxidation of an
alkene? Explain.
H OH
CH3 CH3

OH OH
OH H
(a) CH3CH2 CH2CHCH3 (b) (CH3)2CHC(CH3)2 (c) H (d) H

Solution:
(a) No selectivity
(b) Selectively synthesized
(c)Can’t be formed
(d) Can’t be formed

7.42 What alkenes might be used to prepare the following cyclopropane?

Cl

CH(CH3) 2 Cl
(a) (b)
Solution:
Zn(Cu)
+ (CH3)2CHCHI2 CH(CH3)2
(a) Ether

Cl
OH
+ CHCl3
Cl
(b)

7.43 Predict the products of the following reactions. Don’t worry about the size of the molecule;
concentrate on the functional groups.
Br2

CH3
HBr

CH3

1. OsO4
2. NaHSO3

HO

1. BH3, THF
2. H2O2, OH-

CH2I2, Zn (Cu)

Solution:

CH3

CH3

CH3

CH3

Br2
HO
Br
a) HO Br

CH3
CH3

CH3
CH3

HBr

HO
b) HO Br
 CH3

CH3

CH3

CH3
OsO4
NaHSO3 HO
OH
c) HO OH

CH3
CH3

CH3

CH3

BH3,THF
H2O2,OH
HO

d) HO OH

CH3 CH3

CH3 CH3

CH2I2
Zn(Cu)

HO
e) HO

7.44 The sex attractant of the common housefly is a hydrocarbon with the formula C23H46. On
treatment with aqueous acidic KMnO4, two products are obtained, CH3(CH2)12CO2H and
CH3(CH2)7CO2H.Propose a structure.
Solution:
H2 H H2
H3C C C C C CH3
12 H 7 should be the right structure.

7.45 Compound A has the formula C8H8. It reacts rapidly with KMnO4 to give CO2 and carboxylic
acid, B (C7H6O2), but reacts with only 1molar equivalent of H2 on catalytic hydrogenation over a
palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4 equivalents of
H2 are taken up and hydrocarbon C (C8H16) is produced. What are the structure of A, B, and C?
Write the reactions.
SOLUTION:
 O
H

B C
A C H
OH
C

H2
C
C
CH3

The reactions:

O
H

C
C H
KMnO4 OH
CO2
C

H
H2
C
C H
1mol H2 CH3
C
palladium catalyst
H

H
H2
C
C H
C
4mol H2 CH3

7.46. Plexiglas, a clear plastic used to make many molded articles, is made by polymerization of
methyl methacrylate. Draw a representative segment of Plexiglas.
CH3 O

H2C
Methyl methacrylate
C C OCH3
SOLUTION:
 The segment of Plexiglas:
CH3
H2
C C

C O

OCH3

7.47 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.
O

N-vinylpyrrolidone
Solution:
H H2
* C C *

7.48 Reaction of 2-methylpropene with CH3OH in the presence of H2SO4 catalyst yields methyl
tert-butyl ether, CH3OC(CH3)3, by a mechanism analogous to that of acid-catalyst alkene
hydration. Write the mechanism, using curved arrows for each step.
Solution:
 CH3 CH3
H HSO4
H3C C CH2 + CH3OH H3C C CH3 + CH3OH

CH3 CH3

H3C C CH3 H3C C CH3 + H2SO4

H3C O H H3C O

HSO4

7.49 When 4-penten-1-ol is treated with aqueous Br2, a cyclic bromo ether is formed, rather than the
expected bromohydrin. Propose a mechanism, using curved arrows to show electron movement.
Solution:

H O HO
Br

H
O CH2Br O
Br

7.50 How would you distinguish between the following pairs of compounds using simple chemical
tests? Tell what you would do and what you would see.
(a) cyclopentene and cyclopentane
(b) 2-hexene and benzene
Solution: Bromine in carbon tetrachloride solution is reddish-brown color. Using this one to identify
the double bond by electrophilic addition reaction.

7.51
Cl O Cl O- Cl
+

Cl C C O-Na+ Cl C C O Cl C- O C O

Cl Cl Cl

Cl
+
C
l

C
O
+

+
-

N
a
+
2

Cl

They have the same intermediate which is CCl3-.

7.52
(a) 3
(b) double bonds:2

(c)

7.53 Evidence that cleavage of 1,2-diols by HIO4 occurs through a five membered cyclic periodate
intermediate is based on kinetic data – the measurement of reaction rates. When diols A and B
were prepared and the rates of their reaction with HIO4 were measured, it was found that diol A
cleaved approximately 1 million times faster than diol B. Make molecular models of A and B and
of potential cyclic periodate intermediates, and then explain the kinetic results.

OH
OH

HO
H
H
H

H OH
A B
cis diol trans diol
Solution:

OH

O
HIO4 O
HO
H I OH O
O
O O
H
A:

In cis diol, two –OH are in one plane, so it is easier to form a cyclic periodate inetermediate,
while in trans diol, the two –OH aren’t in one plane, there is larger steric strain in the five
membered cyclic periodate intermediate, it is less stable, so the rates of A is more faster.

7.54 Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis- and
trans-1-3-methylbromocyclohexane and cis- and trans-1-2-methylbromocyclohexane.
The analogous reaction of HBr with 3-bromocyclohexane trans-1, 2-dibromocyclohe-
xane as the sole product. Draw structures of the possible intermediates, and then
Explain why only a single product is formed in the reaction of HBr with 3-bromocyclohexane.

Solution:
 Br Br
Br

H Br
Br

Br

Br

7.55 The following reaction takes place in high yield:

CO2 CH3 CO2 CH3

Hg(OAc)2

AcO Hg

Use your general knowledge of alkene chemistry to propose a mechanism, even though you’ve
never seen this reaction before.
Solution:
 OAc
CO2CH3 CO2CH3

OAc

+
AcO Hg

Hg

AcO

CO2CH3

CO2CH3
H OAc

AcO Hg

AcO Hg

CO2CH3

AcO Hg

7.56 Reaction of cyclohexene with mercury(II) acetate in CH3OH rather than H2O, followed by
treatment with NaBH4, yields cyclohexyl methyl ether rather than cyclohexanol. Suggest a
mechanism.

1.Hg(OAc)2, CH3OH
OCH3
2.NaBH4

Solution:
 OAc OAc
Hg
Hg OAc
HO CH3

HgOAc
HgOAc

O CH3
O CH3
OAc
H

NaBH4
OCH3

7.57 Hydroboration of 2-methyl-2-pentene at 25℃ followed by oxidation with alkaline H2O2 yields
2-methyl-3-pentano, but hydroboration at 160℃ followed by oxidation yields 4-methyl-1-pentanol.
Explain.
CH3

1.BH3,THF,25℃
CH3CHCHCH2CH3
2.H2O2,OH-
CH3 OH

2-Methyl-3-pentanol
CH3C CHCH2CH3

CH3

1.BH3,THF,160℃
CH3CHCH2CH2CH2OH
2.H2O2,OH-
4-Methyl-1-pentanol
Solution:
Case 1:
CH3 CH3
CH3
THF,25℃ H2O2,OH-
3 CH3C CHCH2 CH3 + BH3 3 CH3CH CHCH2CH3
3 CH3CHCHCH2CH3
BH2
OH
Case 2:
 BH2

BH2

H2O2 / OH-

OH
BH2

7.58 Alkynes undergo many of the same reactions that alkenes do. What products would you expect
from each of the following reactions?
CH3
H2 H2
H3C C C C C CH
H
(1) with 1 equiv Br2;
(2) with 2 equiv H2 ,Pd/C
(3)with 1 equiv HBr

Solutions:
(1)
CH3 Br
1 equiv Br2 CH3
H2 H2 H2 H2
H3C C C C C CH H3C C C C C CH
H H
Br

(2)
CH3 2 equiv H2 ,Pd/C CH3
H2 H2 H2 H2 H2
H3C C C C C CH H3C C C C C CH3
H H
(3)

CH3 1 equiv HBr Br

CH3
H2 H2 H2 H2
H3C C C C C CH H3C C C C C CH2
H H

7.59 Explain the observation that hydroxylation of cis-2-butene with OsO4 yields a different product
than hydroxylation of trans -2-butene. First draw the structure and show the stereochemistry of
each product, and then make molecular models.
Solution:
 H3C C C CH3
H H

H3C CH3 H
H3C C
HC CH C CH3
H
cis-But-2-ene trans-But-2-ene

OH
H3C CH3
H3C C
C C C CH3
H H H H
OH OH OH
Butane-2,3-diol Butane-2,3-diol
meso enantiomer
compound