Organic Functional Groups

1. From bonds to functional groups

2. Saturated functional groups
a. Alkanes
b. Amines
c. Ethers
d. Alkyl halides
e. Organometallic compounds
f. Alcohols
3. Unsaturated functional groups
a. Alkenes
b. Alkynes
c. Aldehydes and ketones
d. Carboxylic acids and derivatives
e. Nitriles
4. Aromatic compounds
5. Typical reactions
CHEM2200 Part 2

Functional Groups
1. Functional groups collections of atoms in a molecule that
participate in characteristic reactions
2. How are organic functional groups formed - by combining
and/or bonds

1 CC bond + 1 CC bond

2 CO bonds + 1 CO bond

CHEM2200 Part 2

Saturated Functional Groups (1)

Characteristics
1. Absence of bonds
2. All constituent bonds are single () bonds
3. Important ones are CC, CH, CM, CO, CN, CX (X = Br, Cl, I), NH
and OH bonds
4. Bond polarity and lone pair es
the reaction course

CHEM2200 Part 2

Saturated Functional Groups (2)

1.
2.
3.
4.
5.

Alkanes - contain only CC and CH bonds

Alkyl halides - contain only CC, CX (X = Br, Cl or I) and CH bonds
Alcohols - contain only CC, COH and CH bonds
Ethers - contain only CC, COC and CH bonds
Amines - contain only CC, CN and CH bonds

alkane

alkyl bromide

ether

alcohol

amine

CHEM2200 Part 2

Saturated Functional Groups (3)

Organometallics
1. Contain carbon-metal bond - CLi, CMg, CCu bonds
2. Bond polarity - CM+
3. Can be considered as ionic bonds - C M+
4. Very reactive, react readily with moisture/water to give CH bond
5. Useful functional groups in organic synthesis

CHEM2200 Part 2

Unsaturated Functional Groups (1)

Characteristics
1. Presence of both and bonds
2. Can add H atoms into them and become saturated bonds
3. Important ones are C=C, C=O, C=N, CC, CN bonds and aromatic
rings
4. Bond polarity and lone pair es
the reaction course

CHEM2200 Part 2

Unsaturated Functional Groups (2)

1. Alkenes - contain C=C bond
2. Aldehydes - contain C=O bond, this C atom attaches at least to one H
atom
3. Ketones - contain C=O bond, this C atom does not attach to any H
atoms
4. Carboxylic acids and derivatives - contain either O=CX, O=COH,
O=COC or O=CN bond

alkene

aldehyde

acyl halide carboxylic acid

ketone

ester

CHEM2200 Part 2

amide
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Unsaturated Functional Groups (3)

5. Alkynes - contain CC bond
6. Nitriles - contain CN bond

alkyne

nitrile

CHEM2200 Part 2

Aromatic Compounds
Aromatic compounds contain three C=C bonds in a six-member ring

aromatic compounds

CHEM2200 Part 2

Typical Reactions (1)

1. Alkanes
a. Substitution
CH bond becomes CX (X = Cl, Br, I) bond
Requires X2 and
Q: which CH will react preferentially?

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Typical Reactions (2)

2. Alkyl halides
a. Substitution
CX (X = Cl, Br, I) bond becomes CY (Y = OR, NRR, CN, SR)
bond
Y is usually in the form of an

b. Elimination
Elimination of HX, a
is formed
Requires a
(OH, also an anion!)
Q: When to undergo substitution and when to undergo
elimination?
Q: If there is a choice, where is the position of the C=C bond?

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Typical Reactions (3)

3. Alcohols
a. Substitution
COH bond becomes CX bond
Requires
condition (HX)

b. Elimination
Elimination of H2O, a
bond is formed
Requires
condition
Q: When to undergo substitution and when to undergo
elimination?
Q: If there is a choice, where is the position of the C=C bond?

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Typical Reactions (4)

4. Ethers
a. Normally unreactive
5. Amines
a. Substitution
NH bond becomes
bond
Requires
condition

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Typical Reactions (5)

6. Organometallics
a. Abstraction of H+ - CM bond becomes

b. Sensitive to
c. CM bond becomes

bond

bond

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Typical Reactions (6)

7. Alkenes/alkynes
a. Addition to C=C and CC bond
Requires X2 (light
required)

Requires Y2 or YZ and catalyst

Q: What are the positions of Y and Z if the C=C bond is

unsymmetrical?

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Typical Reactions (7)

8. Aldehydes/ketones
a. Addition to C=O bond

b. Addition to C=O bond followed by elimination of H2O

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Typical Reactions (8)

9. Carboxylic acids and derivatives (RCOY)
a. Order of reactivity

b. Displacement of Y by addition to C=O bond followed by

elimination of Y

reaction at room temperature

reactive

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Typical Reactions (9)

10.Aromatic compounds
a. Substitution of CH bond to become CY bond
A catalyst is needed

Q: Where will Y go if the aromatic Hs are different?

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