Download Exam 3 Fall 00 Chapters 9-13 100points If you do not want your

Exam 3 Fall 00 Chapters 9-13
100points
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Answer all the questions.
1) Give the products (if any) formed in the following reactions: (9pts)
(a)
Ph C C H
(b)
Ph C C H
(c)
Ph C C H
Na, NH3
1) 1 equiv. HBr
2) 1 equiv. HCl
1) NaNH2
2) O
H3C
CH3
3) H3O+
2) Draw the mechanism of one of the above reactions. (12pts)
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3) Fill in the question marks with reagents and products. (12pts)
OH
?
Br Mg, ether
?
H3O+
OH
PCC
?
?
CrO3,H2SO4
O
4) Name (in IUPAC form) the following two compounds. (12pts)
OH
OH
Br
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5) Explain the observation that when one equivalent of HBr is added to 1-pentyne a
single product if formed, yet when one equivalent of HBr is added to 2-pentyne a mixture
of products is formed. (12pts)
H C C CH2CH2CH3
HBr
H
Br
H
CH2CH2CH3
(only product)
CH3 C C CH2CH3
HBr
H3C
Br
H
CH2CH3
(E and Z)
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and
H3C
Br
H
CH2CH3
(E and Z)
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6) For the following compounds, identify the hybridization of each individual carbon
atom. (12.5pts)
OH
CH3CH2 C C CH CH2OH
OH
CH(OH)2
7) Alcohols are weak acids, circle the weaker acid of each pair: (4pts)
a)
b)
OH
OH
CBr3OH
CH3OH
8) Indicate for each reaction if the process is an oxidation, reduction or neither. (8pts)
a) CH3
CH3
OH
b)
OH
O
c) CH3
CH3
OH
d)
OH
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9) Give reagents for the following transformations. (12.5pts)
(a)
(b)
CH3
C-OH
CH3
I
OH
Cl
OH
(c)
OH
(d)
(e)
O
OH
OH
O
OH
10) Draw the products of the following transformations. (6pts)
(a)
H2SO4
OH
Heat
(b)
OH
1) Pyridine, Tos-Cl
2)Na+ -C CCH2CH2CF2Cl
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