Transcript 1. Alcohols, Phenols, and Thiols

Chapter 13 Alcohols, Phenols, and
Thiols
13.1
Alcohols, Phenols, and Thiols
General, Organic, and Biological Chemistry
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Alcohols and Phenols
An alcohol contains
 a hydroxyl group (—OH) attached to a carbon chain
A phenol contains
 a hydroxyl group (—OH) attached to a benzene ring
General, Organic, and Biological Chemistry
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Classification of Alcohols
Alcohols are classified
 by the number of alkyl groups attached to the carbon
bonded to the hydroxyl
 as primary (1°), secondary (2°), or tertiary(3)
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Learning Check
Classify each alcohol as P) primary, S) secondary,
or T) tertiary.
A.
B. CH3—CH2—CH2—OH
C.
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Solution
A.
(S) secondary
B. CH3—CH2—CH2—OH
(P) primary
C.
(T) tertiary
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Guide to Naming Alcohols
General, Organic, and Biological Chemistry
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Naming Alcohols
The names of alcohols
 in IUPAC system replace -e of alkane name with -ol
 that are common names use the name of the alkyl
group followed by alcohol
Formula
IUPAC
CH4
Methane
CH3─OH
Methanol
CH3─CH3
Ethane
CH3─CH2─OH
Ethanol
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Common Name
Methyl alcohol
Ethyl alcohol
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More Names of Alcohols
In IUPAC names for longer carbon chains, the chain is
numbered from the end nearer the –OH group.
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Some Typical Alcohols
“Rubbing alcohol”:
2-Propanol (isopropyl alcohol)
Antifreeze:
1,2-Ethanediol (ethylene glycol)
Glycerol:
1,2,3-Propanetriol
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Learning Check
Give the IUPAC name for each of the following:
A. CH3—CH2—CH2—CH2—OH
B.
OH
C.
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Solution
A. CH3—CH2—CH2—CH2—OH
1-butanol
STEP 1 Name the longest chain attached to OH:
butanol
STEP 2 Number the chain from the end closer to OH:
CH3—CH2—CH2—CH2—OH
4
3
STEP 3 Name alcohol:
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2
1
1-butanol
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Solution (continued)
B.
3-methyl-2-pentanol
STEP 1 Name the longest chain attached to OH:
pentanol
STEP 2 Number the chain from the end closer to OH:
1
2
3
4
5
STEP 3 Name alcohol and any substituents:
3-methyl-2-pentanol
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Solution (continued)
C.
OH
cyclopentanol
STEP 1 Name the longest chain attached to OH:
cyclopentanol
STEP 2 Number the chain from the end closer to OH:
(not necessary with one substituent)
STEP 3 No substituents other than alcohol
STEP 4 Name a cyclic alcohol as cycloalkanol:
cyclopentanol
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Learning Check
Draw the condensed structural formula of the following:
A. 3-Pentanol
B. Propyl alcohol
C. 3-Methylcyclohexanol
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Solution
Draw the condensed structural formula of the following:
A. 3-Pentanol:
B. Propyl alcohol:
CH3 —CH2 —CH2 —OH
C. 3-Methylcyclohexanol:
OH
CH3
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Phenols in Medicine
Phenol
 is the IUPAC name for benzene with a hydroxyl
group
 is used in antiseptics and disinfectants
OH
OH
OH
OH
OH
CH2CH2CH2CH2CH2CH3
Phenol
Resorcinol
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4-Hexylresoricinol
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Naming Phenols
To name a phenol with two substituents,
 assign C-1 to the carbon attached to the –OH
 number the ring to give the lowest numbers
 use prefixes o, m, and p for common names
OH
OH
OH
Cl
Br
Phenol
3-chlorophenol
(m-chlorophenol)
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4-bromophenol
(p-bromophenol)
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Derivatives of Phenol
 Compounds of phenol are the active ingredients in the
essential oils of cloves, vanilla, nutmeg, and mint.
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Learning Check
Draw the condensed structural formula of the following:
A. 3-Pentanol
B. Ethyl alcohol
C. p-Methylphenol
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Solution
Draw the condensed structural formula of the following:
A. 3-Pentanol:
B. Ethyl alcohol:
C. p-Methylphenol:
CH3—CH2—OH
OH
CH3
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Thiols
Thiols
 are organic compounds that
contain a –SH group
 are named in the IUPAC
system by adding thiol to the
alkane name of the longest
carbon chain
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Naming Thiols
 In thiols with long carbon chains, the chain is
numbered to locate the SH group.
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Sources of Thiols
Thiols
 often have strong odors
 are used to detect gas leaks
 are found in onions, oysters, and garlic
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Learning Check
Draw the condensed structural formula of each of the
following compounds:
A. 2-Butanethiol
B. 2-Methyl-1-butanol
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Solution
Draw the condensed structural formula of each of the
following compounds:
A. 2-Butanethiol:
B. 2-Methyl-1-butanol:
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Learning Check
Name each of the following compounds:
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Solution
Name each of the following compounds:
2-Butanol
3-Methyl-1-pentanol
1-Propanethiol
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