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Chapter 12 Organic Compounds with
Oxygen and Sulfur
1
12.1
Alcohols, Phenols, Thiols,
and Ethers
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Alcohols
2
An alcohol contains a hydroxyl group (–OH) that replaces a
hydrogen atom in a hydrocarbon.
A phenol contains a hydroxyl group (–OH) attached to a
benzene ring.
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Naming Alcohols
3
The names of alcohols
• in the IUPAC system replace the -e with -ol
• with 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
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Common Name
methyl alcohol
ethyl alcohol
Copyright © 2012 by Pearson Education, Inc.
Naming Alcohols
4
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Naming of Alcohols
5
Step 1 Name the longest carbon chain with the –OH group.
Name an aromatic alcohol as a phenol.
CH3CH2CH2OH
propanol
OH
CH3CHCH2CH3
CH3
butanol
OH
CH3CHCH2CH2CHCH3
6
5 4
3
2
1
hexanol
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Naming of Alcohols
6
Step 2
Number the chain starting at the end closer to the
–OH.
CH3CH2CH2OH
1-propanol
OH
CH3CHCH2CH3
CH3
2-butanol
OH
CH3CHCH2CH2CHCH3
6
5
4
3
2 1
2-hexanol
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Naming of Alcohols
7
Step 3
Give the location and name of each substituent
relative to the –OH group.
CH3CH2CH2OH
1-propanol
OH
CH3CHCH2CH3
CH3
2-butanol
OH
CH3CHCH2CH2CHCH3
6
5 4
3
2
1
5-methyl-2-hexanol
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Some Typical Alcohols
8
OH
|
“Rubbing alcohol” CH3—CH—CH3
2-propanol (isopropyl alcohol)
Antifreeze HO—CH2—CH2—OH
1,2-ethanediol (ethylene glycol)
OH
|
Glycerol
HO—CH2—CH—CH2—OH
1,2,3-propanetriol
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Learning Check
9
Name the following compounds:
1. CH3—CH2—CH2—CH2—OH
2.
OH CH3
|
|
CH3—CH—CH—CH2—CH3
OH
3.
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Solution
10
Step 1 Name the longest carbon chain with the –OH group.
Name an aromatic alcohol as a phenol.
1. CH3—CH2—CH2—CH2—OH
butanol
OH CH3
|
|
2. CH3—CH—CH—CH2—CH3
pentanol
OH
3.
cyclopentanol
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Solution
11
Step 2
Number the chain starting at the end closer to the
–OH.
1. CH3—CH2—CH2—CH2—OH
1-butanol
OH CH3
|
|
2. CH3—CH—CH—CH2—CH3
2-pentanol
OH
3.
cyclopentanol
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Solution
12
Step 3
Give the location and name of each substituent
relative to the –OH group.
1. CH3—CH2—CH2—CH2—OH
1-butanol
OH CH3
|
|
2. CH3—CH—CH—CH2—CH3
3-methyl-2-pentanol
OH
3.
cyclopentanol
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Phenols in Medicine
13
Phenol is
• the IUPAC name for benzene with a hydroxyl group
• used in antiseptics and disinfectants
OH
OH
OH
OH
OH
CH2CH2CH2CH2CH2CH3
Phenol
Resorcinol
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
4-Hexylresorcinol
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Derivatives of Phenol
14
Compounds of phenol are the active ingredients in the essential
oils of cloves, vanilla, nutmeg, and mint.
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Naming Phenols
15
Step 1 Name the longest carbon chain with the –OH group.
Name an aromatic alcohol as a phenol.
OH
OH
Cl
Br
phenol
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
phenol
Copyright © 2012 by Pearson Education, Inc.
Naming Phenols
16
Step 2
Number the chain starting at the end closer to the
–OH.
OH
OH
1
1
3
4
Cl
Br
phenol
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
phenol
Copyright © 2012 by Pearson Education, Inc.
Naming Phenols
17
Step 3
Give the location and name of each substituent
relative to the –OH group.
OH
OH
1
1
3
4
Cl
Br
3-chlorophenol
4-bromophenol
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Learning Check
18
Write the structure of each of the following:
A.
3-pentanol
B. ethyl alcohol
C.
4-methylphenol
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Solution
19
Write the structure of each of the following:
A. 3-pentanol
OH
|
CH3—CH2—CH—CH2—CH3
B. ethyl alcohol
CH3—CH2—OH
OH
C. 4-methylphenol
CH3
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Thiols
20
Thiols
• contain sulfur
• are similar to alcohols
• contain a thiol (–SH) group
• often have strong odors
• are found in cheese, onions, garlic,
and oysters
• are used to detect gas leaks
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Thiols
21
Thiols are named in the IUPAC system by adding thiol to
the alkane name of the longest carbon chain.
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Ethers
22
An ether
• contains an –O– between two carbon groups
• has a common name that gives the alkyl names of the
attached groups, followed by ether
CH3OCH3
CH3CH2OCH3
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Learning Check
23
Write the structure of the following:
A. 3-pentanol
B. ethanethiol
C. diethyl ether
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Solution
24
A. 3-pentanol
OH
|
CH3CH2CHCH2CH3
B. ethanethiol
CH3CH2SH
C. diethyl ether
CH3CH2OCH2CH3
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.
Ethers as Anesthetics
25
Anesthetics
• inhibit pain signals to the brain
• like diethyl ether, CH3CH2OCH2CH3, were used for over
a century, but caused nausea and were flammable
• developed by the 1960s were nonflammable
Cl F
F
Cl F
H
HCCOCH
F F
F
Ethrane (enflurane)
HCCOCH
H F
H
Penthrane
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright © 2012 by Pearson Education, Inc.