Transcript Chapter 10 Structure and Synthesis of Alcohols

Organic Chemistry, 7e
by L. G. Wade, Jr.
Chapter 10
Structure and Synthesis
of Alcohols
Christine Hermann
Radford University
Radford, VA
Copyright © 2010 Pearson Education, Inc.
10.1 Classify 2,3-dimethyl-2butanol.
a.
b.
c.
d.
0o alcohol
1o alcohol
2o alcohol
3o alcohol
10.1 Answer
a.
b.
c.
d.
0o alcohol
1o alcohol
2o alcohol
3o alcohol
The carbon bearing the –OH has three
other carbons attached to it.
10.2 Give the common name for
(CH3)3CCH2OH.
a.
b.
c.
d.
e.
Tert-pentyl alcohol
Tert-butyl alcohol
Isopentyl alcohol
Isobutyl alcohol
Neopentyl alcohol
10.2 Answer
a.
b.
c.
d.
e.
Tert-pentyl alcohol
Tert-butyl alcohol
Isopentyl alcohol
Isobutyl alcohol
Neopentyl alcohol
10.3 Name
H2C
OH
a.
b.
c.
d.
1-Butanol
2-Butanol
Butane-1,2-diol
Butane-1,2-ol
H
C
OH
CH2CH3
10.3 Answer
a.
b.
c.
d.
1-Butanol
2-Butanol
Butane-1,2-diol
Butane-1,2-ol
Butane is the longest chain; the OHs
are in the 1 and 2 positions.
10.4 Name
a.
b.
c.
d.
1-Ethylphenol
2-Ethylphenol
3-Ethylphenol
4-Ethylphenol
OH
CH2CH2CH3
10.4 Answer
a.
b.
c.
d.
1-Ethylphenol
2-Ethylphenol
3-Ethylphenol
4-Ethylphenol
Phenol is a benzene with an OH attached
and is in position one.
10.5 Give the name of the
alcohol that is in beer and wine.
a.
b.
c.
d.
Methanol
Ethanol
2-Propanol
1-Propanol
10.5 Answer
a.
b.
c.
d.
Methanol
Ethanol
2-Propanol
1-Propanol
The active ingredient in beer and wine is
ethanol.
10.6 Give the common use for
ethane-1,2-diol.
a.
b.
c.
d.
Drinking alcohol
Rubbing alcohol
Vinegar
Antifreeze
10.6 Answer
a.
b.
c.
d.
Drinking alcohol
Rubbing alcohol
Vinegar
Antifreeze
Ethane-1,2-diol (ethylene glycol) is used
as antifreeze; it is very toxic to animals.
10.7
a.
b.
c.
d.
Na
CH3CH2CH2OH
NaCH2CH2CH2OH
CH3CH(Na)CH2OH
CH3CH2CH(Na)OH
CH3CH2CH2ONa
10.7 Answer
a.
b.
c.
d.
NaCH2CH2CH2OH
CH3CH(Na)CH2OH
CH3CH2CH(Na)OH
CH3CH2CH2ONa
Sodium reacts with alcohols to form
alkoxides.
10.8
a.
b.
c.
d.
1. H2C=O
CH3CH2MgBr
CH3CH2CH2OH
CH3CH2OCH3
CH3CH2OH
CH3CH2OMgBr
2. H3O+
10.8 Answer
a.
b.
c.
d.
CH3CH2CH2OH
CH3CH2OCH3
CH3CH2OH
CH3CH2OMgBr
The Grignard reagent adds to the
aldehyde to form an alcohol.
10.9 Identify the alcohol formed
when a Grignard reagent adds to
a ketone.
a.
b.
c.
d.
0o alcohol
1o alcohol
2o alcohol
3o alcohol
10.9 Answer
a.
b.
c.
d.
0o alcohol
1o alcohol
2o alcohol
3o alcohol
A Grignard reagent adds to a ketone to
give, after hydrolysis, a 3o alcohol.
O
10.10
C
CH3CH2
a.
b.
c.
d.
1. 2 CH3MgBr
Cl
3-Methyl-3-pentanol
2-Methyl-2-butanol
2-Methyl-3-butanol
2-Methyl-3-pentanol
2. H3O+
10.10 Answer
a.
b.
c.
d.
3-Methyl-3-pentanol
2-Methyl-2-butanol
2-Methyl-3-butanol
2-Methyl-3-pentanol
Two methyls add to the carbonyl
carbon, followed by hydrolysis.
O
1. 2 CH3MgBr
10.11
C
CH3CH2
a.
b.
c.
d.
OCH2CH3 2. H3O+
3-Methyl-3-pentanol + methanol
2-Methyl-2-butanol + ethanol
2-Methyl-3-butanol + methanol
2-Methyl-3-pentanol + ethanol
10.11 Answer
a.
b.
c.
d.
3-Methyl-3-pentanol + methanol
2-Methyl-2-butanol + ethanol
2-Methyl-3-butanol + methanol
2-Methyl-3-pentanol + ethanol
Two methyls add to the carbonyl carbon,
followed by hydrolysis. The ethoxide is
protonated.
O
10.12
1.
CH3CH2MgCl
a.
b.
c.
d.
CH3CH2CH(OH)CH3
CH3CH2OH
CH3CH2CH2OH
CH3CH2CH2CH2OH
2. H3O+
10.12 Answer
a.
b.
c.
d.
CH3CH2CH(OH)CH3
CH3CH2OH
CH3CH2CH2OH
CH3CH2CH2CH2OH
Grignard reagents add to epoxide to yield
an alcohol that is two carbons longer.
10.13 Give the reason why
Grignard reactions must have dry
glassware.
a. Grignard reagents react vigorously
and irreversibly with water.
b. Magnesium dissolves in water.
c. The alkyl halide dissolves in water.
d. Grignard reagents do not react with
water.
10.13 Answer
a. Grignard reagents react vigorously
and irreversibly with water.
b. Magnesium dissolves in water.
c. The alkyl halide dissolves in water.
d. Grignard reagents do not react with
water.
10.14 Identify the compounds that
sodium borohydride reduces.
a. Aldehydes and ketones
b. Esters and carboxylic acids
c. Aldehydes, ketones, esters, and
carboxylic acids
d. Alkenes and alkynes
10.14 Answer
a. Aldehydes and ketones
b. Esters and carboxylic acids
c. Aldehydes, ketones, esters, and
carboxylic acids
d. Alkenes and alkynes
O
10.15
1. NaBH4
C
H2C
a.
b.
c.
d.
CH
CH2COOH
CH2=CHCH(OH)COOH
CH3CH2CH(OH)COOH
CH2=CHCH(OH)CH2OH
CH3CH2CH(OH)CH2OH
2. H3O+
10.15 Answer
a.
b.
c.
d.
CH2=CHCH(OH)COOH
CH3CH2CH(OH)COOH
CH2=CHCH(OH)CH2OH
CH3CH2CH(OH)CH2OH
Sodium borohydride reduces ketones, but
does not reduce alkenes or carboxylic
acids.
10.16 Identify the compounds that
lithium aluminum hydride
reduces.
a. Aldehydes and ketones
b. Esters and carboxylic acids
c. Aldehydes, ketones, esters, and
carboxylic acids
d. Alkenes and alkynes
10.16 Answer
a. Aldehydes and ketones
b. Esters and carboxylic acids
c. Aldehydes, ketones, esters, and
carboxylic acids
d. Alkenes and alkynes
O
10.17
1. LiAlH4
C
H2C
a.
b.
c.
d.
CH
CH2COOH
CH2=CHCH(OH)COOH
CH3CH2CH(OH)COOH
CH2=CHCH(OH)CH2OH
CH3CH2CH(OH)CH2OH
2. H3O+
10.17 Answer
a.
b.
c.
d.
CH2=CHCH(OH)COOH
CH3CH2CH(OH)COOH
CH2=CHCH(OH)CH2OH
CH3CH2CH(OH)CH2OH
Lithium aluminum hydride reduces
ketones and carboxylic acids.
10.18 Identify the compounds that
hydrogen and Raney nickel
reduces.
a. Aldehydes and ketones
b. Esters and carboxylic acids
c. Aldehydes, ketones, esters, and
carboxylic acids
d. Alkenes and alkynes
e. Aldehydes, ketones, alkenes, and
alkynes
10.18 Answer
a. Aldehydes and ketones
b. Esters and carboxylic acids
c. Aldehydes, ketones, esters, and
carboxylic acids
d. Alkenes and alkynes
e. Aldehydes, ketones, alkenes, and
alkynes
O
10.19
H2C
a.
b.
c.
d.
Raney Ni
C
CH
CH2COOH
CH2=CHCH(OH)COOH
CH3CH2CH(OH)COOH
CH2=CHCH(OH)CH2OH
CH3CH2CH(OH)CH2OH
H2
10.19 Answer
a.
b.
c.
d.
CH2=CHCH(OH)COOH
CH3CH2CH(OH)COOH
CH2=CHCH(OH)CH2OH
CH3CH2CH(OH)CH2OH
Hydrogen and Raney nickel reduce
ketones and alkenes.
10.20
a.
b.
c.
d.
boiling
CH3CH2CH2SH
CH3CH2CH2SOH
CH3CH2CH2SO2H
CH3CH2CH2SO3H
CH3CH2CH2SO4H
HNO3
10.20 Answer
a.
b.
c.
d.
CH3CH2CH2SOH
CH3CH2CH2SO2H
CH3CH2CH2SO3H
CH3CH2CH2SO4H
A thiol is oxidized to a sulfonic acid in the
presence of boiling nitric acid.