Download Functional Groups - Manasquan Public Schools

ORGANIC CHEMISTRY
Any molecule that
contains the element
CARBON
SUBSTITUTED
HYDROCARBONS
Organic
Chemistry
Hydrocarbons
ONLY
Carbon
and Hydrogen
Alkene
Alkane
Alkyne
Ring
(Benzene)
Substituded
Substituded Hydrocarbons
Hydrocarbons + Halogens
+ Oxygen
Substituded
Hydrocarbons
+ Nitrogen
Amine
Amide
Alcohol
aldehyde
organic
acid
ketone
ester
ether
Substituted
Hydrocarbons
23.1 Introduction to Functional
Groups
Organic compounds
> can be classified
according to their functional groups.
A functional group is a specific
arrangement of atoms in an organic
compound that identify it as part of a
specific family.
Note that the double and triple bonds of
alkenes and alkynes are considered
the functional groups.
5
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
Identify the Functional
Group
23.1 Introduction to Functional
Groups
>
Halocarbons
What is the general formula of a
halocarbon?
• A halocarbon is an organic compound
that contains at least one covalently
bonded fluorine, chlorine, bromine, or
iodine atom.
Chloroethene
7
Chloromethane
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
23.1 Introduction to Functional
Groups
>
Alcohols
What do mouthwash, perfume, and
hairspray have in common?
They all contain an alcohol of
some type.
An alcohol is an organic
compound with an —OH group.
Ethanol
8
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
23.1 Introduction to Functional
Groups
9
>
Interpret Data
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
Compounds with Oxygen
Atoms
Alcohols
• contain a hydroxyl
group (-OH)
Phenols
•
contain a benzene ring
with a hydroxyl group.
10
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Alcohols are named
• with an IUPAC name that replaces the e in
alkane name with ol
CH4
methane
CH3─OH
methanol
CH3─CH3
ethane
CH3─CH2─OH
ethanol
11
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Naming Alcohols
12
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Name the following Alcohol
CH3
OH
│
│
CH3─CH─CH2─CH2─CH─CH3
STEP 1 Name the longest carbon chain with
the OH group.
A six-carbon chain attached to an OH is
hexanol
13
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Naming an Alcohol (continued)
STEP 2 Number the chain starting at the
end closer to the OH group.
CH3
OH
│
│
CH3─CH─CH2─CH2─CH─CH3
6
5
4
3
2
1
STEP 3 Give the location and name of
each substituent relative to the OH
group.
5-methyl-2-hexanol
14
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Name the
CH3
following:
│
CH3─CH2─CH ─CH2─OH
4
3
2
1
STEP 1 Name the longest carbon chain with the OH
group. A four-carbon chain attached to an OH is
butanol.
STEP 2 Number the chain starting at the end closer to
the OH group.
STEP 3 Give the location and name of each substituent
relative to the OH group.
2-methyl-1-butanol
15
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Give the IUPAC name for the
following:
OH CH3
|
|
CH3—CH—CH—CH2—CH3
1
2
3
4
5
STEP 1 Name the longest carbon chain with the OH
group. A five-carbon chain attached to an OH is
pentanol.
STEP 2 Number the chain starting at the end closer to
the OH group.
STEP 3 Give the location and name of each substituent
relative to the OH group.
16
Basic Chemistry
3-methyl-2-pentanol
Copyright © 2011 Pearson Education, Inc.
23.3 Carbonyl Compounds >
Carboxylic Acids
The general formula of a carboxylic
acid is RCOOH.
17
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
23.3 Carbonyl Compounds >
Carboxylic Acids
In the IUPAC system, carboxylic acids are
named by replacing the -e ending of the
parent structure with the ending -oic acid.
• The carboxylic acid CH3COOH
is named ethanoic acid.
18
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
23.3 Carbonyl Compounds >
Interpret Data
Some Saturated Aliphatic Carboxylic Acids
Molecular
formula
19
Carbon
IUPAC name
atoms
Common
name
Melting
point (°C)
HCOOH
1
Methanoic acid
Formic acid
8
CH3COOH
2
Ethanoic acid
Acetic acid
17
CH3CH2COOH
3
Propanoic acid
Propionic acid
CH3(CH2)2COOH
4
Butanoic acid
Butyric acid
–6
CH3(CH2)4COOH
6
Hexanoic acid
Caproic acid
–3
CH3(CH2)6COOH
8
Octanoic acid
Caprylic acid
16
CH3(CH2)8COOH
10
Decanoic acid
Capric acid
31
CH3(CH2)10COOH
12
Dodecanoic acid
Lauric acid
44
CH3(CH2)12COOH
14
Tetradecanoic acid
Myristic acid
58
CH3(CH2)14COOH
16
Hexadecanoic acid Palmitic acid
63
CH3(CH2)16COOH
18
Octadecanoic acid
70
Stearic acid
–22
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
23.3 Carbonyl Compounds >
Carboxylic Acids
Lemons and limes contain citric acid, a
carboxylic acid that gives citrus fruits their
sour flavor.
20
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
Carboxylic acids are named
• in the IUPAC system by replacing the e in the alkane
name of the longest carbon chain with oic acid
H─COOH
methanoic acid
formic acid
CH3─COOH
ethanoic acid
acetic acid
CH3─CH2─COOH
propanoic acid
CH3─CH2─CH2─COOH
21
Basic Chemistry
butanoic acid
Copyright © 2011 Pearson Education, Inc.
Naming Carboxylic Acids
22
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Give the IUPAC name of the
following Carboxylic Acid
CH3
|
CH3—CH—CH2—COOH
STEP 1 Identify the carbon chain containing the
carboxyl group and replace the e in the alkane
name with oic acid.
butanoic acid
23
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Example of Naming a
Carboxylic Acid (continued)
STEP 2 Give the location and name of each substituent
on the main chain by counting the carboxyl group as
carbon 1.
CH3
|
CH3—CH—CH2—COOH
4
3
2
1
3-methylbutanoic acid
24
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Give the IUPAC name for the
CH
CH
following:
3
3
|
|
CH3─CH─CH2─CH─COOH
5
4
3
2
1
STEP 1 Identify the carbon chain containing the carboxyl
group and replace the e with oic acid.
pentanoic acid
STEP 2 Give the location and name of each substituent
on the main chain by counting the carboxyl group as
carbon 1.
2,4-dimethylpentanoic acid
25
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
23.3 Carbonyl Compounds >
Aldehydes and Ketones
Aldehydes and Ketones
What structural characteristic do an
aldehyde and a ketone share?
• A carbonyl group: it is a
functional group with the
general structure C O.
26
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
23.3 Carbonyl Compounds >
Interpret Data
Some Common Aldehydes
IUPAC name
(common name)
Structural formula
Ball-and-stick
model
Methanal
(formaldehyde)
Ethanal
(acetaldehyde)
Benzaldehyde
(benzaldehyde)
27
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
23.3 Carbonyl Compounds >
Interpret Data
Some Common Ketones
IUPAC name
(common name)
Structural formula
Ball-and-stick model
Propanone
(acetone)
Diphenylmethanone
(benzophenone)
28
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
23.3 Carbonyl Compounds >
29
29
Naming
Aldehydes
23.3 Carbonyl Compounds >
Give the IUPAC name for
the following:
Aldehyde
Cl
O
│
║
CH3─CH2─CH─CH2─C─H
STEP 1 Name the longest carbon chain
containing the carbonyl group by replacing
the e in the alkane name with al.
pentanal
30
30
Aldehyde
(continued)
23.3 Carbonyl Compounds >
STEP 2 Name and number substituents by
counting the carbonyl group as carbon 1.
Cl
O
│
║
CH3─CH2─CH─CH2─C─H
5
4
3
2
1
3-chloropentanal
31
31
23.3 Carbonyl Compounds >
Draw the condensed structural
formula for 2,3-dichloropropanal.
STEP 1 Draw the main chain of carbon atoms.
Propanal has three carbon atoms with an aldehyde
group.
O
║
C─C─C─H
3
2
1
STEP 2 Number the chain and place the substituents
on carbons indicated by the numbers.
32
32
23.3 Carbonyl Compounds >
Solution (continued)
Cl Cl O
│ │ ║
C─C─C─H
3
2
1
STEP 3 Add the correct number of hydrogen
atoms.
Cl
Cl O
│
│ ║
CH2─CH─C─H
2,3-dichloropropanal
33
33
23.3 Carbonyl Compounds >
Naming Ketones
In the name for a ketone, the
• IUPAC name replaces the e in the alkane name
by one
• common name identifies the alkyl groups
attached to the carbonyl group in alphabetical
order and adds the word ketone
34
34
23.3 Carbonyl Compounds >
35
35
Naming Ketones
23.3 Carbonyl Compounds >
Give the IUPAC name for the following
Ketone
O
║
Cl─CH2─CH2─C─CH2─Cl
STEP 1 Name the longest carbon chain
containing the carbonyl group by replacing
the e in the alkane name with one.
butanone
36
36
Naming a Ketone
(continued)
23.3 Carbonyl Compounds >
STEP 2 Number the carbon chain starting from
the end nearer the carbonyl group and
indicate its location.
O
║
2-butanone
Cl─CH2─CH2─C─CH2─Cl
4
3
2
1
STEP 3 Name and number any substituents on
the carbon chain.
1,4-dichloro-2-butanone
37
37
23.3 Carbonyl Compounds >
name for the
following:
CH3 O
│ ║
CH3─CH2─CH─C─CH2─CH3
STEP 1 Name the longest carbon chain containing
the carbonyl group by replacing the e in the
alkane name with one.
hexanone
38
38
23.3 Carbonyl Compounds >
Solution
STEP 2 Number the carbon chain starting from the end
nearer the carbonyl group and indicate its location.
CH3 O
│
║
CH3─CH2─CH─C─CH2─CH3
6
5
4
3
2
1
3-hexanone
STEP 3 Name and number any substituents on the carbon
chain.
CH3 O
│
║
CH3─CH2─CH─C─CH2─CH3
6
5
4
39
39
3
2
1
4-methyl-3-hexanone
23.1 Introduction to Functional
Groups
>
Ethers
What is the general formula of an
ether?
• An ether is an organic compound in which
oxygen is bonded to two carbon groups.
40
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
23.1 Introduction to Functional
Groups
>
Ethers
Diethyl ether was the first reliable
general anesthetic.
• However, because
diethyl ether is highly
flammable and often
causes nausea, it was
eventually replaced by
other anesthetics.
41
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
Ethers
• contains an ─O─ between two carbon atoms
• has a common name of the two alkyl names
followed by ether
42
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Write the condensed structural
formula of diethyl ether.
This ether contains an ─O─ attached to
two ethyl groups (CH3─CH2─ ).
CH3─CH2─O─CH2─CH3
43
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
23.3 Carbonyl Compounds >
Esters
Esters are probably the most pleasant
and delicious organic compounds one can
study.
• Many esters have pleasant, fruity odors.
• Esters give blueberries, pineapples, apples,
pears, bananas, and many other
fruits their characteristic aromas.
• They also give many perfumes
their fragrances.
44
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
23.3 Carbonyl Compounds >
Esters
The general formula of an ester is
RCOOR.
45
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
Esterification
• is the reaction between a carboxylic acid
and an alcohol
• uses an acid catalyst and heat
O
║
H+, heat
CH3 — C—OH + HO—CH2—CH3
O
║
CH3 — C—O—CH2—CH3 + H2O
46
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Write the equation for the reaction of
propanoic acid and methyl alcohol
when heated in the presence of an acid catalyst.
O
║
H+, heat
CH3—CH2—C—OH + HO—CH3
O
║
CH3—CH2—C—O—CH3 + H2O
47
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Esters
In an ester, the H in the carboxyl group is replaced with
an alkyl group.
O
║
CH3—C—O—CH3
ester group
48
Basic Chemistry
The ester methyl ethanoate (methyl acetate) is
made from methyl alcohol and ethanoic acid
(acetic
Copyright
acid).
© 2011 Pearson Education, Inc.
The name of an ester includes
• name of the alkyl group from the alcohol
• the name of the carbon chain from the acid
with the ic acid ending replaced by ate
49
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Naming Esters
50
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Example of Naming an Ester
Give the IUPAC and common names of the
following compound, which is responsible for
the flavor and odor of pears:
O
║
CH3—C—O—CH2—CH2—CH3
STEP 1 Write the name of the carbon chain
from the alcohol as an alkyl group. The alkyl
group with three carbon atoms is propyl.
51
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Example of Naming an Ester
(continued)
STEP 2 Change the ic acid of the acid name to ate.
In the IUPAC name, ethanoic acid is named
ethanoate.
O
║
propyl
CH3—C—O—CH2—CH2—CH3
ethanoate
propyl ethanoate (IUPAC)
propyl acetate (common)
52
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Give the IUPAC for the following
O
║
CH3—CH2—CH2—C—O—CH2—CH3
STEP 1 Write the name of the carbon chain from the alcohol
as an alkyl group.
ethyl
STEP 2 Change the ic acid of the acid name to ate.
O
butanoate
║
ethyl
CH3—CH2—CH2—C—O—CH2—CH3
53
ethyl butanoate (IUPAC)
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Draw the condensed structural
formula of ethyl propionoate.
O
propionate ║
ethyl
CH3—CH2 —C—O—CH2—CH3
54
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
23.1 Introduction to Functional
Groups
>
Amines
Ethanamine
What is the general
formula of an amine?
• An amine is an organic compound in
which nitrogen is bonded to a carbon
group.
55
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
Amines
• are derivatives of
ammonia, NH3
• contain N attached
to one or more alkyl
or aromatic groups
56
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Naming Simple Amines
Simple amines have common names that list the
alkyl groups attach to the N atom followed by
amine.
57
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
23.1 Introduction to Functional
Groups
>
Amines
The -e ending of the parent hydrocarbon is
changed to -amine.
– Ethanamine is used to make plastics, pharmaceuticals,
and pesticides.
– Benzenamine is used to make furniture foam and some
of the dyes that give clothes their colors.
Benzenamine
Ethanamine
58
Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.
Learning Check
Give the common name for each of the following:
A.
CH3—NH—CH2—CH3
ethylmethylamine
B.
CH3
|
CH3—CH2—N—CH2—CH3
diethylmethylamine
59
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
Draw the condensed structural
formulas for
methylpropylamine
CH3–CH2–CH2–NH–CH3
60
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.
23.1 Introduction to Functional
Groups
>
Identify Family and Functional Group
Amine
aldehyde
Alkene
Ketone
Acid
Alkane
61
alcohol
acid
halogen
alcohol
halogen
acid
ester
alcohol
Chapter 17 – Organic Chemistry
4. The IUPAC name for isopropyl alcohol
is:
A.
B.
C.
D.
1–propanol
2–phenol
2–propanol
2–propanol
1,2,3–propanetriol
Chapter 17 – Organic Chemistry
5. The correct name of CH3-O-CH2CH3 is:
A.
B.
C.
D.
diethyl ether
ethyl ether
methyl ethyl
methyl
ethylether
ether
ethyl methyl oxide
Concept Map
65
Basic Chemistry
Copyright © 2011 Pearson Education, Inc.