Alkene Reaction Practice Iverson CH320M/328M Do Not Turn In

NAME (Print): _____________________________ Chemistry 320M/328M

Dr. Brent Iverson
Practice Homework
SIGNATURE: _____________________________ October 19, 2012

Please print the

first three letters
of your last name
in the three boxes

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Alkene Reaction Practice Iverson CH320M/328M Do Not Turn In

1. (3-5 pts each) The following reactions all involve chemistry of alkenes. Fill in the box with the
product(s) that are missing from the chemical reaction equations. Draw only the predominant
regioisomer product or products (i.e. Markovnikov or non-Markovnikov products) and please
remember that you must draw the structures of ALL the product stereoisomers using wedges and
dashes to indicate stereochemistry. When a racemic mixture is formed, you must write "racemic"
under all of the structures EVEN THOUGH YOU DREW ALL OF THE STRUCTURES.

Br
A. CH3 HBr CH3CHCH3
(not chiral)

OH
B. 1. Hg(OAc)2 H2O
CH3 CH3CHCH3
2. NaBH4
(not chiral)

C. 1. BH3
CH3 CH3CH2CH2OH
2. H2O2 / HO
(not chiral)

Br Br
D. Br2
CH3
Br Br
Racemic

Cl Cl
E. Cl2
CH3
OH OH
H2O
Racemic

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Alkene Reaction Practice Iverson CH320M/328M Do Not Turn In

1. (cont.) (3-5 pts each) The following reactions all involve chemistry of alkenes. Fill in the box with
the product(s) that are missing from the chemical reaction equations. Draw only the predominant
regioisomer product or products (i.e. Markovnikov or non-Markovnikov products) and please
remember that you must draw the structures of all the product stereoisomers using wedges and
dashes to indicate stereochemistry. When a racemic mixture is formed, you must write "racemic"
under all of the structures EVEN THOUGH YOU DREW ALL OF THE STRUCTURES.

CH3 Cl
Cl CH3
F. Cl2
H Cl
Cl H

Racemic Mixture

CH3 CH3
OH OH
G. H CH3
H2O CH3 H
Racemic
H2SO4 OH OH
(catalytic)
CH3 CH3
H CH3
CH3 H

H. 1. BH3 OH OH
2. H2O2 / HO

Racemic Mixture

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Alkene Reaction Practice Iverson CH320M/328M Do Not Turn In

2. (3 or 5 pts each) For the following reactions, fill in the boxes with the appropriate structures. I know
this is pretty hard, but I think it will be a great way to study your alkene and alkyne reactions. Work
together if that helps.

CH3
1. BH3
2. H2O2 / HO OH
H
Racemic
CH3

H
OH
CH2Br

Br 1. H2O Hg(OAc)2
H 2. NaBH4
Racemic
CH2Br Br2

H
Br

OH

Not chiral

H2O H2SO4 (catalytic amount)

1. O3
O
2. (CH3)2S

This is the only organic product.

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Alkene Reaction Practice Iverson CH320M/328M Do Not Turn In

3. (3 pts each) For the following reactions, fill in the boxes with the starting material that leads to the
predominant product or products.
H Br

C C Br H
* * H * *
Br2
Br C C
H
Racemic Br

OH OH
H2O
H2SO4
(catalytic amount)
Racemic

OH
1. BH3

2. H2O2 / HO

OH
1. BH3 H3C H CH3
C C
* * CH3 * * H
2. H2O2 / HO H H C C

Racemic H3C OH

Cl
HCl
or

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Alkene Reaction Practice Iverson CH320M/328M Do Not Turn In

4. (23 pts.) Read these directions carefully. For the reaction shown below, fill in the details of
the mechanism for the rearranged product only. Although non-rearranged product is also
formed, we are not interested in that mechanism. Draw the appropriate chemical structures
and use an arrow to show how pairs of electrons are moved to make and break bonds during
the reaction. Be sure to write all lone pairs of electrons and all formal charges. Finally, in the
boxes provided by the arrows, write which kind of mechanistic element is being indicated,
such as "make a bond", "add a proton", etc.

H H
H Add a proton
H H H
H O H
H O
H
H
H CH3
2 carbocation
CH3

Rearrangement

H H
Make a bond
H
H H
H H
H O H
CH3 H
H
O
Not chiral
CH3
H 3 carbocation
(more stable)
Take a
H O H proton away

Not chiral

Is the starting material chiral? Yes

H CH3
Is the rearranged product chiral? No
H O H OH
Rearranged Product