68

Chapter 2

Structure and Reactivity

Table 2-3

Common Functional Groups

General structurea Functional group Example

Compound class

Alkanes (Chapters 3, 4) Haloalkanes (Chapters 6, 7)

RO H RO X(X F, Cl, Br, I)

None O X

CH3CH2CH2CH3
Butane

CH3CH2 OBr
Bromoethane

Alcohols (Chapters 8, 9) Ethers (Chapter 9) Thiols (Chapter 9) Alkenes (Chapters 11, 12) Alkynes (Chapter 13)

RO OH

O OH

H A (CH3)2C O OH
2-Propanol (Isopropyl alcohol)

RO O O R

O OO

O O CH3 CH3CH2 O
Methoxyethane (Ethyl methyl ether)

RO SH (H)R (H)R R(H) R(H)

O SH

SH CH3CH2 O
Ethanethiol

G D CPC D G

G D CPC D G

CH3 CH3

G C P CH2 D

2-Methylpropene

(H)RO C q C O R(H) R(H) (H)R

OCq CO

CH3C q CCH3
2-Butyne

CH3 R(H) C C C C C HC HC C CH CH

Aromatic compounds (Chapters 15, 16, 22)

C C

C C

(H)R

R(H)

R(H) O B RO C O H O B R O C O R O B RO C O O OH O O B B RO C O O O C O R(H) O B (H)RO C O O O R O B O C OH O B OCO O B O C O OH O O B B O C O OOCO O B OCO OO

C H

Methylbenzene (Toluene)

Aldehydes (Chapters 17, 18)

O B CH3CH2CH
Propanal

Ketones (Chapters 17, 18)

O B CH3CH2CCH2CH2CH3
3-Hexanone

Carboxylic acids (Chapters 19, 20)

O B CH3CH2COH
Propanoic acid

Anhydrides (Chapters 19, 20) Esters (Chapters 19, 20, 23)

a

O O B B CH3CH2COCCH 2CH3
Propanoic anhydride

O B 3 CH3CH2COCH
Methyl propanoate (Methyl propionate)

The letter R denotes an alkyl group (see text). Different alkyl groups can be distinguished by adding primes to the letter R: R9, R0, and so forth.

2-3 Functional Groups: Centers of Reactivity

Chapter 2

69

Table 2-3

(continued)
General structure Functional group Example

Compound class

Amides (Chapters 19, 20, 26) Nitriles (Chapter 20) Amines (Chapter 21)

O B RO C O N O R(H) A R(H) RO C q N

O B D O C O N G O C q N

O B 2 CH3CH2CH2CNH
Butanamide

CH3C q N
Ethanenitrile (Acetonitrile)

RO N O R(H) A R(H)

D O N G

(CH3)3N
N, N-Dimethylmethanamine (Trimethylamine)

Many functional groups contain polar bonds

Polar bonds determine the behavior of many classes of molecules. Recall that polarity is due to a difference in the electronegativity of two atoms bound to each other (Section 1-3). We have already introduced the haloalkanes, which contain polar carbon halogen bonds as their functional groups. In Chapters 6 and 7 we shall explore their chemistry in depth. Another functionality is the hydroxy group, O H, characteristic of alcohols. The characteristic functional unit of ethers is an oxygen bonded to two carbon atoms (OCOOOC O). The functional group in alcohols and in some ethers can be converted into a large variety of other functionalities and are therefore important in synthetic transformations. This chemistry is the subject of Chapters 8 and 9. Haloalkanes Alcohols .. .. CH3 O CH3CH2 O ..H ..H
Methanol Ethanol
(Wood alcohol) (Grain alcohol)

Chloromethane (Methyl chloride)

.. CH3Cl .. :

Chloroethane (Ethyl chloride)

.. CH3CH2 Cl .. :

Methoxymethane (Dimethyl ether)

(A refrigerant)

.. CH3 O . . CH3

Ethers

.. CH3CH2 O . . CH2CH3
Ethoxyethane (Diethyl ether)
(An inhalation anesthetic)

(Topical anesthetics)

The carbonyl functional group, CPO, is found in aldehydes, in ketones, and, in conjunction with an attached 2OH, in the carboxylic acids. Aldehydes and ketones are discussed in Chapters 17 and 18, the carboxylic acids and their derivatives in Chapters 19 and 20. Aldehydes O B HCH
Formaldehyde
(A disinfectant)

Ketones O B CH3CCH3
Acetone

Carboxylic Acids O B or HCOOH HCOH or HCO2H

Formic acid
(Strong irritant)

O B CH3CH or CH3CHO
Acetaldehyde
(A hypnotic)

O B CH3CH2CCH3
Butanone (Methyl ethyl ketone)

(Common solvents)

O B or CH3COOH CH3COH or CH3CO2H

Acetic acid
(In vinegar)