Organic Chemistry, 9e
by L. G. Wade, Jr.
Homework
Chapter 11
Reactions of
Alcohols
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2017 Pearson Education, Inc.
11.1
a)
b)
c)
d)
(CH3)2CHOH
(CH3)2C=O
CH3CH2COOH
No reaction
2017 Pearson Education, Inc.
11.2
a)
b)
c)
d)
CH3COOH
CH3CH2COOH
CH3CH2CHO
No reaction
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11.3
a)
b)
c)
d)
CH3COOH
CH3CH2COOH
CH3CH2CHO
No reaction
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11.4
a)
b)
c)
d)
(CH3)3COH
(CH3)2C=O
CH2=C(CH3)2
No reaction
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11.5 Identify the reagent that is not used to oxidize a
primary alcohol to a carboxylic acid.
a)
b)
c)
d)
HNO3
PCC
Na2Cr2O7, H2SO4
CrO3, H2SO4
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11.6
a)
b)
c)
d)
CH3CH2CH2OTs
CH3CH2CH2OCl
CH3CH2CH2Cl
CH3CH2CH2Ts
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11.7
a)
b)
c)
d)
e)
CH3CH2CH2OTs
CH3CH2CH2OCl
CH3CH2CH2Cl
CH3CH2CH2Ts
CH3CH2CH3
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11.8
a)
b)
c)
d)
(CH3)2CHBr
CH3CH2Br
CH3CH2CH2Br
BrCH2CH2CH2Br
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11.9
a)
b)
c)
d)
(CH3)2CHCH2Br
(CH3)3CBr
CH3CH2CH2CH2Br
BrCH2CH2CH2CH2Br
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11.10
a)
b)
c)
d)
CH3CH2CH2OPBr3
CH3CH2CH2OBr
CH3CH2CH2Br
CH3CH2CH2PBr2
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11.11
a)
b)
c)
d)
CH3CH2CH2OSCl2
CH3CH2CH2Cl
CH3CH2CH2OCl
CH3CH2CH2SO2H
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11.12 Identify the products in the dehydration of
butan-2-ol, in the presence of sulfuric acid.
a)
b)
c)
d)
But-1-ene
cis-But-2-ene
trans-But-2-ene
All of the above
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11.13 Identify the true statement regarding the reaction
of propan-1-ol with sulfuric acid.
a)
b)
c)
d)
140 àgives dipropyl ether.
180 àgives dipropyl ether.
140 àgives dipropyl ether + propene.
180 àgives dipropyl ether + propene.
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11.14
a)
b)
c)
d)
2,3-Dimethyl-3-hydroxybutan-2-one
2,3-Dimethylbutane-2,3-dione
2,3-Dimethylbutane-2,3-diol
3,3-Dimethylbutan-2-one
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11.15
a)
b)
c)
d)
CH3CH2COOCH3
CH3COOCH2CH3
CH3CH2COOCH2CH3
CH3COOCH3
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11.16
a)
b)
c)
d)
CH3OSO3H
CH3OSO3CH3
CH3OSO2CH3
CH3OSO2H
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11.17
a)
b)
c)
d)
CH3ONO2
CH3NO2
CH3ONO
CH3OH
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11.18
a)
b)
c)
d)
CH3OPO(OH)2
(CH3O)2PO(OH)
(CH3O)3PO
CH3OCH3
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11.19
a)
b)
c)
d)
CH3CH3
CH3CH2OCH3
CH3OCH3
CH3CH2OCH2CH3
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Organic Chemistry, 9e
by L. G. Wade, Jr.
Homework
Chapter 12
Spectroscopy and
Mass Spectrometry
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2017 Pearson Education, Inc.
12.1 Identify the region with the longest wavelength.
a)
b)
c)
d)
e)
X rays
Ultraviolet
Visible
Infrared
Microwave
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12.2 Identify the region with the highest energy.
a)
b)
c)
d)
e)
X rays
Ultraviolet
Visible
Infrared
Microwave
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12.3 Which of the following is not one of the infrared
vibrations?
a)
b)
c)
d)
e)
Bouncing
Wagging
Scissoring
Rocking
Twisting
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12.4 Identify the frequency that indicates an alkene.
a)
b)
c)
d)
1660 cmJ1700 cmJ2200 cmJ3300 cmJ2017 Pearson Education, Inc.
12.5 Identify the frequency that indicates a C bond
stretching frequency for an alkane.
a)
b)
c)
d)
1660 cmJ2900 cmJ3050 cmJ3300 cmJ2017 Pearson Education, Inc.
12.6 Identify the C bonding frequency with the
highest wavenumber.
a)
b)
c)
d)
sp
sp2
sp3
sp4
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12.7 What compound has a formula of C5H8 and a peak at
3300 cm
a)
b)
c)
d)
Alkane
Alkene
Internal alkyne
Terminal alkyne
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12.8 What compound has a formula of C5H12O and a peak
at 3300 cm
a)
b)
c)
d)
Ether
Alcohol
Aldehyde
Ketone
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12.9 What compound has a formula of C6H15N and two
peaks at 3300 cm
a)
b)
c)
1!mide
2!mide
3!mide
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d)
e)
f)
1!mine
2!mine
3!mine
12.10 What compound has a formula of C5H10O and
peaks at 1710, 2700, and 2800 cm
a)
b)
c)
d)
Ketone
Aldehyde
Ester
Carboxylic acid
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12.11 What compound has a formula of C5H10O2, a peak
at 1715, and a broad peak at 3000 cm
a)
b)
c)
d)
Aldehyde
Ketone
Carboxylic acid
Ester
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12.12 In IR spectroscopy, give the effect of C=C
conjugation on the C=O stretch of an aldehyde.
a)
b)
c)
d)
It lowers the C=O stretching frequency.
It raises the C=O stretching frequency.
The C=O stretching frequency is unaffected.
The C=O stretching frequency is changed.
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12.13 Identify mass spectroscopy.
a)
b)
c)
d)
Stretching and bending of bonds
Fragmentation of the molecule
Interaction between hydrogens
Separates mixtures into components
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12.14 Identify the species measured in mass
spectroscopy.
a)
b)
c)
d)
e)
Anions
Cations
Radicals
Cations and radical cations
Anions and radical anions
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12.15 Define base peak.
a)
b)
c)
d)
Lowest m/z peak
Highest m/z peak
Weakest peak
Strongest peak
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12.16 Explain why the bromide isotopes are recognizable.
a)
b)
c)
d)
The M+2 is half the size of the M.
The M+2 is twice the size of the M.
The M+2 is the same size as the M.
Only one isotope is seen.
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12.17 Explain why the chloride isotopes are recognizable.
a)
b)
c)
d)
The M+2 is one-third the size of the M.
The M+2 is three times the size of the M.
The M+2 is the same size as the M.
Only one isotope is seen.
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12.18 Give the fragment at m/z 29 in the mass spectrum of
pentane.
a)
b)
c)
d)
CH3CH2ƒH3CH2+
CH3CH2ƒH3CH2
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12.19 Give the fragment at m/z 42 in the mass spectrum of
propan-1-ol.
a)
b)
c)
d)
CH3CH=CH2+
CH3CH=CH2ƒH3CH=CH2ƒH3CH=CH2 +© 2017 Pearson Education, Inc.
12.20 Identify a possibility for a fragment at m/z 43 in the
mass spectrum.
a)
b)
c)
d)
CH3CH2CH2+
CH3CH2CH3+
CH2=C=CH2+
CH3CH=CH2+
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