General organic and biological chemistry structures off life 5th CH13 alcohols phenols thiols ethers GOB structures 5th ed

Lecture Presentation

Chapter 13
Alcohols,
Phenols, Thiols,
and Ethers
Karen C. Timberlake
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Chapter 13
Alcohols, Phenols, Thiols, and Ethers
Anesthesia is typically
administered by a nurse
anesthetist who provides care
before, during, and after a
medical procedure. A nurse
anesthetist gives medications
to keep a patient asleep and
pain-free while monitoring the
patient’s vital signs.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Chapter 13 Readiness

Core Chemistry Skills
• Naming and Drawing Alkanes (12.2)

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


13.1 Alcohols, Phenols, Thiols, and Ethers
Functional groups such as
OH
• an alcohol contain a hydroxyl
CH3 OH
group (— OH).
Phenol
Methanol
• a phenol contain a hydroxyl
group (— OH) bonded to a
benzene ring.
CH3—CH2—SH
• a thiol contain an — SH group.
Learning Goal Give the IUPAC and common names for
alcohols, phenols, and thiols; draw their condensed and
line-angle structural formulas.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.

Alcohols, Phenols, and Thiols

Core Chemistry Skill Identifying Alcohols, Phenols,
and Thiols
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Naming Alcohols
• In the IUPAC system, replace the e with ol.
• With common names, use the name of the alkyl
group followed by alcohol.

Core Chemistry Skill Naming Alcohols and Phenols
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Naming Alcohols
• For alcohols with three or more carbon atoms, number the
carbons in the chain to give the position of the — OH
group and any substituents on the chain.
• An alcohol with two — OH groups is named as a diol. An
alcohol with three — OH groups is named as a triol.

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Naming Cyclic Alcohols
A cyclic alcohol is named as a cycloalkanol.
• If there are substituents, the ring is numbered
from carbon 1, which is the carbon attached to
the — OH group.
• Compounds with no substituents on the ring do
not require a number for the hydroxyl group.

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Naming Phenols
• The term phenol is the IUPAC name when a hydroxyl group
(— OH) is bonded to a benzene ring.
• When there is a second substituent, the benzene ring is
numbered starting with carbon 1, bonded to the — OH group.
• The terms ortho, meta, and para are used for the common
names of simple phenols.
• The common name cresol is also used for methylphenols.

General, Organic, and Biological Chemistry: Structures of Life, 5/e

Karen C. Timberlake

© 2016 Pearson Education, Inc.


Guide to Naming Alcohols

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Study Check
Give the IUPAC name for the following compound:

CH3
CH3 —CH—CH2

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

CH2

OH
CH

CH3

© 2016 Pearson Education, Inc.

Solution
Give the IUPAC name for the following compound:

CH3
CH3 —CH—CH2
ANALYZE
Given
THE
alcohol, six-carbon
PROBLEM

CH2

OH
CH

CH3

Need
IUPAC name

chain, methyl substituent

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.

Naming of Alcohols
Give the IUPAC name for the following compound:

CH3
CH3 —CH—CH2

CH2

OH
CH

CH3

STEP 1 Name the longest carbon chain attached to
the — OH group by replacing the e in the
corresponding alkane name with ol.

CH3
CH3 —CH—CH2

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

CH2

OH
CH

CH3

© 2016 Pearson Education, Inc.


Solution
Give the IUPAC name for the following compound:

CH3
CH3 —CH—CH2

CH2

OH
CH

CH3

STEP 2 Number the chain starting at the end nearer to
the — OH group.
  2-hexanol

CH3
CH3 —CH—CH2

CH2

OH
CH

CH3

6           5           4            3             2            1          
       

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Solution
Give the IUPAC name for the following compound:

CH3
CH3 —CH—CH2

CH2

OH
CH

CH3

STEP 3 Give the location and name for each substituent
relative to the — OH group.

CH3
CH3 —CH—CH2

CH2

OH
CH

CH3

6           5           4            3             2            1          
          5-methyl-2-hexanol

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Study Check
Give the IUPAC name for the following compound:
CH3

A.
B.

CH3

Br

CH

OH
CH2

CH

CH3

OH

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Solution
Give the IUPAC name for the following compound:
CH3

A.

CH3

CH

ANALYZE
THE
PROBLEM

OH
CH2

CH

CH3

Given
Need
alcohol, five-carbon chain
methyl substituent  

IUPAC name

                             

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Solution
Give the IUPAC name for the following compound:
Br

OH

B.

ANALYZE
THE
PROBLEM

Given
phenol,
bromo substituent

Need
IUPAC and
common name

                             
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Solution
STEP 1 Name the longest carbon chain attached to the
— OH group by replacing the e in the corresponding
alkane name with ol. Name an aromatic alcohol as a
phenol.
A.
B.

CH3
CH3

Br

CH

OH
CH2

CH

OH

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

CH3

pentanol
phenol

© 2016 Pearson Education, Inc.


Solution
STEP 2 Number the chain starting at the end closer to
the — OH. The compound is a phenol because it
consists of an — OH group attached to a
benzene
ring.
A.

CH3
4
CH

5
CH3

B.
Br

3

3
CH2

2

OH
2
CH

OH

1
CH3

2-pentanol
phenol

1

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Solution
STEP 3 Give the location and name for each substituent
relative to the — OH group.
A.
B.

CH3
4
CH

5
CH3

Br

3

3
CH2

2

OH
2
CH

1

CH3

4-methyl-2-pentanol

OH
1

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

3-bromophenol

© 2016 Pearson Education, Inc.


Chemistry Link to Health:
Alcohols and Phenols
Methanol (methyl alcohol), the
simplest alcohol,
• is found in many solvents
and paint removers.
• is oxidized to formaldehyde
when ingested and can
cause headaches,
blindness, and death.

General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.

Chemistry Link to Health:
Alcohols and Phenols
Ethanol (ethyl alcohol)
• has been known since prehistoric times as
an intoxicating product.
• is formed by the fermentation of grains,
sugars, and starches.
Fermentation

C6H12O6  2CH3—CH2—OH + 2CO2
• is used as a solvent for perfumes,
varnishes, and some medicines, such as
tincture of iodine.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Chemistry Link to Health:
Alcohols and Phenols
1,2-ethanediol (ethylene glycol)
• is used as an antifreeze in heating and cooling systems.
• is also a solvent for paints, inks, and plastics.
• is used in the production of synthetic fibers such as Dacron.
If ingested, it is extremely toxic. In the body, it is oxidized to oxalic
acid, which forms insoluble salts in the kidneys that cause renal
damage, convulsions, and death.

OH
HO
H C C H
H
H
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.


Chemistry Link to Health:
Alcohols and Phenols
• Bisphenol A (BPA) is used to make polycarbonate, a
clear plastic that is used to manufacture beverage
bottles, including baby bottles.
• Washing polycarbonate bottles with certain detergents
or at high temperatures disrupts the polymer, causing
small amounts of BPA to leach from the bottles.
CH3
HO

C

OH

CH3
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake

© 2016 Pearson Education, Inc.