Chapter 22
Organic Chemistry,
Polymers, and Biochemicals
Chemistry: The Molecular Nature
of Matter, 7E
Jespersen/Hyslop
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1
Carbon Chemistry
Bonding
 Strong covalent bonding to itself and to other nonmetal elements
 Capable of forming extremely long carbon-carbon
chains
 Multiple arrangements of
identical molecular formulas
lead to numerous isomers.
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2
Structural Formula Representations
Lewis Structure of Pentane
Condensed Structural Formula
 CH3CH2CH2CH2CH3 pentane
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Structural Formula Representations
 Lewis Structure of Pentan-1-ol
 Condensed Structural Formula
CH3CH2CH2CH2CH2OH 1-pentanol
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4
Chiral Isomers of Carbon
Chirality exists when carbon has four unique
constituents bond to itself
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|
|
|
Non-superimposable mirror images
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5
Chiral Isomers of Butan-2-ol
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Abbreviated or Bond-Line Structure
Carbon atoms occur at intersection but no
symbol used
CH3–CH2–CH3 would appear as:
Non-carbon atoms would appear as symbols
CH3–CH2–CH2–OH would appear as:
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Abbreviated or Bond-Line Structure
Open-Chain Compounds
Examples
butane
butane-1-ol
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Abbreviated or Bond-Line Structure of
Ring Compounds
Cyclohexane
Chair Form of
Cylcohexane
Cyclopropane
Benzene
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Abbreviated or Bond-Line Structure
Heterocyclic Compounds
Piperazine
Pyridine
Tetrahydropyran
Pyrazole
Furan
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Learning Check
1. Draw at least two geometric isomers of C4H10
using abbreviated structures.
1. Draw the four carbon chain first
2. Now rearrange CH3 groups
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11
Your Turn!
When a chemical formula is written in the following
form, CH3CH2CH2COOH, the representation is
known as
A. an abbreviated structure
B. a Lewis dot structure
C. a condensed formula
D. an optical isomer
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12
Functional Groups in Organic
Chemistry
 Organic families can be defined by functional
groups.
 Frequently use “R” as a place holder for alkanelike hydrocarbon groups
R–OH
alcohol
R–COOHorganic acid
R–O–R’ ether
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13
Functional
Groups in
Organic
Chemistry
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14
Learning Check
1. Write the abbreviated structure for benzoic
acid.
2. What family does C6H5NH2 belong to?
1.
2. amine family
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15
Your Turn!
Which of the following is an example of an ester?
A.CH3CH2CH2OH
B.
C.
D.
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16
Your Turn!
The functional group, OH, is found in which
one of these types of organic compounds?
A)Ethers
B)Alcohols
C)Alkenes
D)Alkanes
E)Amines
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Hydrocarbons
 Hydrocarbon compounds only contain C and H
 Alkanes
CnH2n+2
CH3CH2CH3 propane
 Alkenes
CnH2n
CH3CHCH2 propene
 Alkynes
CnH2n-2
CH3CCH
 Aromatic
C6H6
propyne
benzene
 Characterized by cyclic delocalized π bonding
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18
Hydrocarbons
 Alkanes are defined as saturated compounds.
 All singles bond to carbon
 Cannot add more hydrogen atoms
 Alkenes and alkynes are unsaturated
compounds.
 Alkenes have double bonds and H atoms can be
added to the double bond to create a saturated
compound.
 Alkynes have triple bonds and H atoms can be
added to create a saturated compound.
 CH2=CHCH3 + H2
Pt ¾®
¾ ¾
CH3CH2CH3
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19
Aromaticity
- Characterized by conjugated bonds in a ring such
as benzene.
- π electrons are delocalized over the ring
- Leads to greater stability than expected
- Properties are different than those of other
hydrocarbon families
- Polycyclic examples:
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20
Hydrocarbon Nomenclature
Rules for naming alkanes
Established by IUPAC
1. Name ends in “-ane”
2. Complete name uses that of parent
compound with constituent groups added.
3. Parent is longest continuous carbon chain.
4. Name of longest chain based on the number
of carbons.
5. Carbon atoms are numbered starting at the
end that gives the lowest number for the
first branch.
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21
Straight Chained Alkanes
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Alkyl Groups
Alkane type groups added to parent chain are
known as alkyl groups. Consist of alkane,
minus one H atom. Name always ends in –yl
Example
CH4 : now remove one H which yields –CH3


Naming of –CH3
Start with parent name, which is methane


Drop –ane and add –yl
So methane becomes methyl group
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23
Alkyl Groups
 CH3CH2CH3 yields –CH2CH2CH3 when one H atom is
removed from the end carbon.
 The name of the aryl group is propyl.
 Note, you can have another isomer of propyl.
 The other isomer’s aryl group is 1-methylethyl, or
isopropyl, and is created when the H atom is removed
from the non-terminal carbon.
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24
Nomenclature
6. Aryl groups names are prefixed to parent
name.
7. Multiple aryl groups on a parent are
numbered and named alphabetically.
8. When there are multiple identical groups add
di, tri, tetra to the aryl name.
9. If multiple, identical aryl groups are attached
to the same carbon repeat the carbon
number.
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Examples
What is the name of the compound shown?
1. The longest carbon chain (parent) is four. Parent
name is butane.
2. Start numbering from the left to get the smallest
number for the attached group.
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Examples
3. The attached alkyl group is a methyl
group.
 Thus, the correct name is:
 2-methylbutane
 What is the name of the following compound?
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Examples
 The parent chain contains five carbons.
 Thus, the parent name is pentane.
 Number from the left to obtain the smallest number
for the first alkyl group.
 The alkyl groups are at the 2 and 3 positions.
 The 2 and 3 positions each contain a methyl group.
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Examples
 Thus, the correct name is:
 2,3-dimethylpentane
 Let’s consider an alkane with two substituents
on the same carbon.
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Examples
 The parent chain is six carbons long.
 The lowest correct numbering of positions is
shown below.
 There are methyl and ethyl groups attached to
carbon 3.
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Examples
 The correct name is:
3-ethyl-3-methylhexane
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31
Your Turn!
What is the correct name for the molecule shown
below?
A. 3-butylpentane
B. 1,1-diethylpentane
C. 3-ethylheptane
D. 5-ethylheptane
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32
Your Turn!
What is the name of the compound shown below?
A. 3-methyl-3-methyloctane
B. 3,3-dimethyloctane
C. 2-ethyl-2-methylheptane
D. 6,6-dimethyloctane
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33
Your Turn!
 What is the IUPAC name (don’t worry about
geometric isomers) for CH3CH=CHCH3?
A) butene-2
B) butene-3
C) 2-butene
D) 2-butyne
E) 2-butyl
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34
Your Turn!
What is the IUPAC name for H2C=CHCH=CH2?
A) butene-2
B) 1,3-dibutene
C) 1,3-butadiene
D) butane-1,3
E) 2-butynel
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35
Chemical Properties of Alkanes
 Alkanes are relatively unreactive
 Not reactive in conc. NaOH or H2SO4 at room
temperature.
 React with hot HNO3
 Will react with Cl2 and Br2 to form halogenated
hydrocarbons.
 Examples are CH3Cl, CH2Cl2 and CHCl3
 Can crack molecules like ethane under controlled
conditions to form CH2CH2
 Will react with O2 to form CO2, CO, and H2O
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Alkenes and Alkynes
 Alkenes contain one or more double bonds
 General form: CnH2n
 Alkynes contain one or more triple bonds
 General form: CnH2n-2
 Non-polar compounds are not water soluble
 Examples:
Ethene or ethylene
Ethyne or acetylene
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Alkenes and Alkynes
 Nomenclature
 The parent chain must contain the multiple bond
even if it is a smaller chain length than one without
a multiple bond
 Number from end that gives the lowest number to
the first carbon of the multiple bond
 The number is given as -x- and placed just before
the –ene or –yne of the parent name.
 For example, but-2-ene. The double bond starts on
carbon 2 of the chain.
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Alkene Examples
 Start numbering from the left to get the lowest
number for the first carbon with the double bond
 The parent is heptene and the correct naming
including the double bond location would be
hep-2-ene
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39
Alkene Example
 The parent chain is four carbons
 2,3-dimethylbut-2-ene
 We would not name this 2-methyl-3methylbut-2-ene
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Naming Polyenes
 How do we name compounds such as the following?
 This compound contains two double bonds and is
known as a diene
 We want the lowest number for the first carbon of
each of the double bonds
 Start numbering from the right
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41
Naming Polyenes
 The correct name would be hex-1,3-diene
 Three double bonds would be a triene
hex-1,3,5-triene
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Cyclic Alkenes
 Number ring to obtain lowest number for first
carbon of the double bond
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43
Cyclic Alkenes
 Correct name is 1,6-dimethylcyclohex-1-ene
 Other ring examples
Cyclopentene
Cyclooctene
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44
Your Turn!
What is the correct name for the compound shown
below?
A. 1,4-dimethylcyclopent-1-ene
B. 1,3-dimethylcyclopent-1-ene
C. 1-methyl-4-methylcyclopent-1-ene
D. 1,3-dimethylcyclo-1-pentene
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45
Your Turn!
What is the correct structure for 3,3-dimethylpro-1-ene?
A.
B.
C.
D.
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Geometric Isomers
 Groups cannot freely rotate about a double bond
 Therefore, it is possible to have geometric
isomers
 Examples:
trans-1,2-dibromoethene
cis-1,2-dibromoethene
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Reactions of Alkene
 Alkenes readily add across the double bond
 Examples of an addition reaction:
 CH2CH2 + H2 ¾ ¾Pt ¾® CH3CH3 hydrogenation
 CH2CH2 + HCl → CH3CH2Cl
 CH2CH2 + H2O → CH3CH2OH
 CH2CH2 + Cl2 → CH2ClCH2Cl
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Aromatic Hydrocarbons
 The most common aromatic compound is
benzene and its derivatives
 Representation of bonding
 Delocalized π bonds create unique stability,
called resonance stabilization. The circle in the
ring represents delocalization.
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Reactions
 Substitution reactions maintain benzene’s
resonance structure.
 Addition reactions, like those of alkenes, destroy
resonance structure
 Substitution reaction:
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Addition Reaction
Notice that you have reduced the double bonding
in the ring and altered the resonance stabilization
of the ring
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Learning Check:
What product would form if benzene reacted with
nitric acid using an appropriate catalyst?
 Sulfuric acid is the catalyst
 A substitution reaction occurs
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Your Turn!
Which product is most likely formed when sulfuric
acid reacts with benzene?
A.
B.
C.
D.
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Organic Compounds Containing Oxygen
Important functional groups:
Alcohol
Ether
Aldehyde
Ketone
Carboxylic acid
Ester
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Alcohols and Ethers
 Common alcohols: names end in –ol
 CH3OH methanol
 CH3CH2OH ethanol
 CH3CH2CH2OH propan-1-ol
 If the –OH group was attached to the central carbon
then the alcohol would be propan-2-ol
 Alcohols form hydrogen bonds, causing their boiling
points to be higher than predicted.
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55
Alcohols and Ethers
 Primary alcohols:
 Secondary alcohols:
 Tertiary alcohols:
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Alcohols and Ethers
 Common ethers:
 CH3OCH3
 CH3CH2OCH2CH3
 CH3OCH2CH3
dimethyl ether
diethyl ether
methyl ethyl ether
 No hydrogen bonding occurs, thus, boiling
points are lower than corresponding
alcohols
 Like alkanes, ethers are not very reactive
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Reactions of Alcohols
 Alcohols can undergo oxidation to form a variety
of products. Oxidation removes an H atom from
the alcoholic carbon as well as the H on the –OH
group.
 Primary alcohols can be oxidized to aldehydes
and carboxylic acids
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Reactions of Alcohols
 Aldehydes are more readily oxidized than
alcohols
 Secondary alcohols can be oxidized to ketones
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Reactions of Alcohols
 Ketones are not further oxidized
 Tertiary alcohols have no H atom on the
alcoholic carbon and thus, do not undergo
oxidation
 Alcohols undergo elimination reactions in the
presence of concentrated H2SO4 forming water
and alkenes
 –OH group readily accepts a proton from sulfuric
acid
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Elimination Reaction
 Dehydration of an alcohol
 During the reaction a very unstable carbocation
is formed. This ion eliminates a proton to form
the alkene.
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Substitution Reactions of Alcohols
 Using heat and concentrated HBr, HI, or HCl, a
halogen will replace the –OH group
2-bromo-2-methylpropane
 A proton adds to the –OH forming –OH2+
 Water leaves and the halogen ion attaches to the
carbon site where the –OH was attached
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Your Turn!
Name the following compound.
CH2OH
CH3CH2CHCH2CH3
A) 3-penatanol
B) 2-ethyl-1-butanol
C) 3-methyl-3-pentanol
D) 2-propyl-1-propanol
E) hexanol
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63
Your Turn!
Which of the following compounds is an alcohol?
A) CH3CH2CH2CO2H
B) CH3-O-CH3
C) CH3CO2CH3
D) CH3CH2CH=O
E) CH2OH-CH2OH
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Aldehydes and Ketones
Aldehyde group
Keto group
 Naming aldehydes
 Parent name ends in –al, replacing –e in the alkane
name
 The aldehyde group is always at the end of a chain
and numbering starts with that end of the chain
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Naming Aldehydes
3-methylpentanal
 Number from the aldehyde end
 Do not use -1- for aldehyde:
 3-methylpropan-1-al, or 3-methyl-1-propanal
would be wrong
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66
Learning Check
What is the name of the following aldehyde?
4-ethylhexanal
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Naming Ketones
 Parent name ends in –one
 Parent chain must contain carbonyl group
 Numbering so carbonyl carbon has lowest
possible number
4-ethylheptan-3-one
NOT: 4-ethylheptan-5-one
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Your Turn!
What is the correct name for the aldehyde shown
below?
A. 2,4-dimethylpentanal
B. 2,4-dimethyl-1-pentanal
C. 2-methyl-4-methylpropanal
D. 2,4-dimethyl-5-pentanal
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Your Turn! - Solution
 Aldehydes are numbered from the aldehyde end
of the molecule
 There are two identical groups, (methyl) so we
use –di in the naming
 2,4-dimethylpentanal
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Your Turn!
What is the correct name for the ketone shown
below?
A. 4-methyl-3-ethylhexan-2-one
B. 4-ethyl-3-methylhexan-5-one
C. 3-ethyl-4-methylhexan-2-one
D. 3,4-diethylpentan-2-one
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Your Turn! - Solution
 Number to give lowest number to keto group so
you start from the right
 Alkyl groups are ordered alphabetically so ethyl
comes before methyl
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Reactions of Aldehydes and Ketones
 Aldehydes and ketones add hydrogen across the
C=O bond
 Process is hydrogenation or reduction
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Carboxylic Acids and Esters
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Naming Carboxlic Acids
 Name ends in –oic, replacing –e in the parent
name
 Numbering begins with carboxyl group
 –COOH or –CO2H is the condensed form
 CH3COOH is ethanoic acid (acetic acid)
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Naming Carboxylic Acids
 Benzoic acid
 Propanoic acid
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Naming Esters
 Name begins with alkyl group attached to the –O
 Name of parent acid is separate from the alkyl
group name and –oic is replaced with –ate
 Ethyl propanate
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Learning Check
 What is the name of the following ester?
 Alkyl group is propyl
 Number, starting with
the ester carbon
 Propyl 4-methylpentanate
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Your Turn!
What is the correct name for the product when 3methylbutan-1-ol is completely oxidized?
A. 3-methylbutanoic acid
B. 2-methyl-1-butanoic acid
C. 2-methlybutan-1-oic acid
D. 3-methylbutan-1-oic acid
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Your Turn!
The compound below has which functional groups?
A) ketone and ester
B) ketone, alcohol, and carboxylic acid
C) ether, ketone, and aldehyde
D) ether and aldehyde
E) ketone and aldehyde
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Reactions of Carboxylic Acids
 The –COOH is weakly acidic and therefore reacts
with base
 RCOOH + OH–
→ RCOO– + H2O
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Formation of Esters
 Esters give fruits their characteristic odor
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Saponification
 Strong base reacts with an ester to form alcohol
and the ester’s anion forms
pentanoate ion
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Your Turn!
Name the ester formed when methanol reacts with
hexanoic acid.
A. 1-methyl hexanoate
B. methylhexanoate
C. methyl hexanoate
D. methyl hexan-1-oate
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Organic Derivatives of Ammonia
 Amines are derived from ammonia with one or
more H atoms replaced with organic groups
 Like ammonia, amines are weakly basic
 Amines react with aczids
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Acid Property of Protonated Amines
 Ethylmethylammonium ion is the conjugate acid
of ethylmethylamine
pKa = 10.76
pKb= 3.24
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Amides
 General form
 Where (H)R indicates either an H atom or an R
group attached
 Naming
 The name of the parent acid is amended dropping
the –oic ending and replacing it with –amide
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Example Names of Amides
 Propanamide
 4-ethylhexamide
 These are examples
of simple amides
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Synthesis of Simple Amides
 An organic acid reacts with aqueous NH3 to form
an amide
2-methylpropanoic acid yields 2-methylpropanamide
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Amide Reactions
 Amides can be hydrolyzed back to their acid
form producing ammonia in the process
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Amide Reactions
 Urea, an amide, ultimately hydrolyzes to NH3,
CO2 and water
 Carbonic acid is formed, which then decomposes
to carbon dioxide and water
 The overall reaction is:
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91
Basicity of Amides
 Amides are not basic like amines
 The lone pair on the N atom is delocalized and
thus not readily available for donation to a
proton
 Amides are neutral in an acid-base sense
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92
Your Turn!
What is the correct name for the molecule shown
below?
A. 4,5-dimethylhexanamide
B. 2,3-dimethyl-6-hexanamide
C. 4-methyl-5-methylhexanamide
D. 4-isopropyl-4-methylpropanamide
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