Chemistry 104 Worksheet: Nucleophilic Substitution & Radical Polymerization - Prof. Christ, Exams of Chemistry

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Chemistry 104 AID Discussion Section Worksheet^ Discussion Section #

Key Ideas from Lecture #28: Nucleophilic substitution:

Radical Polymerization:

Let's think about these concepts for a bit... How is radical polymerization similar to radical halogenation? How is it different?

Problems:

Fall 2006, Exam #3, Problem 11

11. A short segment of the PVDF polymer is shown below. What monomer is used as the reactant in the radical polymerization?

~

(c) (d) (e)

1,2-difluoroethene 1,I-difluoroethene 1,I-difluoroethane 1,2-difluoroethane 1,1,3,3-tetrafluorethane

i54n

f

I

~F

Spring 2007, Exam #3, Problem 9

9. Given the following polymer structure, determine what monomer would be used to create

the polymer (Step 1). Once you have determined what the monomer is, "react" it with one mole ofHBr (Step 2). Name that product.

Step 1 radical monomer polymerization

Step 2 monomer + HBr ..^ answer

1

Chemistry 104 AID Discussion Section Worksheet^ Discussion Section #

Fall 2008, Quiz #6, Problem #

1. (18 points, 2 points each) Predict the major product of the following reactions. If you think that no reaction will take place, indicate this by writing no reaction. You DO NOT have to show mechanisms to get full credit on these problems, you only need to show the major product.

2 mol iOH

acid cat

PCC

o 0

~OH

LiAIH.t

• activator^ ry",

HBr.

• /'""--OH

acid cat Uo O~

V-H

2

>-0--<

t- 1<2-

C)

H

aH cJ H ..

0 acid cat u

)lOH (^) u""-

+ /OH -^

+- Ii)..-u

cS

KMn04 (^). 11'\0 (^) r )< """"\

U

acid cat (^) -

do"'

+ O