Chapter 10 Lecture Notes

Chapter 10 Lecture Notes: Carboxylic Acids, Amines, and Amides

Educational Goals
1. Given the structure of a carboxylic acid, carboxylate ion, ester, amide, or amine molecule, be
able to give the systemic names and vice versa.
2. Know and understand the intermolecular forces that attract carboxylic acid, amine, or amide
molecules to one another, and how these forces affect boiling points and melting points.
3. Identify amines as primary (1o), secondary (2o), or tertiary (3o). Compare and contrast amines
and quaternary ammonium ions.
4. Predict the products for the reactions of carboxylic acids with water, alcohols, amines, ammonia,
or with strong bases.
5. Predict the products for the reactions of amines with water or with strong acids.
6. Predict the products for the base-catalyzed hydrolysis of an ester.
7. Predict the products for the acid-catalyzed hydrolysis of an amide.
8. Identify chiral carbon atoms in structural formulas. Given the number of chiral carbons in a
molecule, determine the number of stereoisomers.
9. Define the term enantiomer. Compare and contrast enantiomers and diastereomers.

Carboxylic Acids

From now on, we will write “R” instead

of “Hydrocarbon” in structures.

Naming Carboxylic Acids

• When naming a carboxylic acid according to the IUPAC

rules, the parent is the longest continuous carbon chain

that ____________________ the

____________________ _____________________.

• Numbering __________________________ at
the carbonyl carbon, and alkyl groups are identified by
name, position, and number of appearances

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 Chapter 10 Lecture Notes

• Example:

• IUPAC names for carboxylic acid parent chains are formed by dropping the final “e” on the name

of the corresponding hydrocarbon and adding “______________________”.

propanoic acid 3-methylbutanoic acid

You try it:

Name: _______________________________________

Draw structures of each the carboxylic acids:

a. 2-methylpentanoic acid b. 4-ethylhexanoic acid

Some carboxylic acids use common names:

methanoic acid = formic acid
ethanoic acid = acetic acid (vinegar is a 5% acetic acid solution)
Group work: Draw each molecule.
NOTE: When named as a substituent, -OH is hydroxy, -Cl is chloro, and -Br is bromo.
a. butanoic acid b. 2-hydroxypropanoic acid

c. 4-chlorohexanoic acid d. 2-chloro-3-hydroxydecanoic acid

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 Chapter 10 Lecture Notes

Properties of Carboxylic Acids

• Compared to other organic compounds with a

similar molecular weight, carboxylic acids have
relatively high boiling points due to their ability to form _______________
___________________with one another.

• The ability to form hydrogen bonds, in addition to the presence of polar C=O, C-O, and O-H

bonds, gives small carboxylic acids a significant water_______________________.

• An increasing number of carbon atoms leads to a ______________________in water solubility.

Molecule Water Solubility

Condensed Structure
Name (g/100 mL)
methanoic
HCOOH miscible*
acid
ethanoic acid CH COOH
3 miscible
propanoic acid CH CH COOH 3 2 miscible
butanoic acid CH CH CH COOH
3 2 2 miscible
pentanoic acid CH CH CH CH COOH
3 2 2 2 3.7
hexanoic acid CH CH CH CH CH COOH
3 2 2 2 2 1.0

Common Carboxylic Acids

Formic acid, HCOOH: Chemical that is present in the sting of ants.

Acetic acid, CH3COOH: dilute (5%) aqueous acetic acid is known as vinegar
Butyric acid, CH3CH2CH2COOH: Chemical responsible for odor of rancid butter.
Caproic acid, CH3CH2CH2CH2CH2COOH: First isolated from the skin of goats-which has distinct smell.
Citric acid: Present in citrus fruits and blood.

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 Chapter 10 Lecture Notes

Reactions of Carboxylic Acids

1) Reaction with Water

Carboxylic acids are_______________________ _________________________.

• Acid strengths of common carboxylic

acids are about the same as that for acetic
acid.

Remember this from chapter 9?

• For the acid (HA) and its conjugate base (A-),

HA + H2 O A- + H3 O+
• There is more HA when the pH is lower than the pKa.
• There is more A- when the pH is higher than the pKa.
• There are equal amounts of HA and A- when the pH = pKa

2) Neutralization: Reaction with OH-

Carboxylic acids undergo _____________________ _________________________with bases and
produce water and a carboxylic acid salt.

• The resulting carboxylate ions are _______________ ____________________in water than the
carboxylic acids themselves.
• The ions have a full charge = more water soluble.
Solubility of Carboxylate Ions
In general, carboxylate anions with 12 or more carbon atoms, like palmitate ion, are_________________,
while those with fewer than 12 carbon atoms are water soluble.

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 Chapter 10 Lecture Notes

Summary: Solubility of Carboxylic Acids and their Conjugate Bases

Naming Carboxylate Ions

• To name a carboxylate ion, the ending on the name (IUPAC or common) of the related carboxylic
acid is changed from “ic acid” to “ate”.

• Example:
– acetic acid becomes
acetate ion

• Palmitic acid becomes palmitate ion

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 Chapter 10 Lecture Notes

You try it:

Draw and name the conjugate base (carboxylate ion) for the following carboxylic acids:

Other Reactions of Carboxylic Acids

3) Esterification
• Esterification is carried out by warming a mixture of a carboxylic acid and an alcohol in the
presence of a strong acid catalyst.

Note that the reaction is reversible!

Esters undergo hydrolysis to give back the carboxylic acid.
– we saw this in chapter 6!
Ester hydrolysis reactions can be catalyzed by either an acid or a base. Here is the net result:

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 Chapter 10 Lecture Notes

Naming Esters

• When naming an ester, place the name of the alkyl group (R’) in front of
the name of the carboxylate part (RCOO) as follows:

Example:

You try it:

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 Chapter 10 Lecture Notes

4) Decarboxylation of Carboxylic Acids

• Break the COOH off, and replace the H!

• Common in biological systems for keto-acids

• Keto acids are carboxylic acids with ketone functionality (carbonyl groups)

You Try It! Draw the products of each decarboxylation reaction.

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 Chapter 10 Lecture Notes

Summary of Reactions of Carboxylic Acids:

1) Reaction with water:

2) Neutralization (reaction with OH-):

3) Esterification (reaction with alcohol):

4) Decarboxylation:

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 Chapter 10 Lecture Notes

Amines
________________________are compounds that contain one or more organic groups bonded to
nitrogen.

• They are classified as primary, secondary, and tertiary according to how many _______________
are bonded to the nitrogen atom.
• primary (1°) - only one organic group (R) is attached to the amine nitrogen atom
• secondary (2°) - two organic groups attached to the amine nitrogen
• tertiary (3°) - three organic groups attached to the amine nitrogen

In a primary, secondary, or tertiary amine, the amine nitrogen has a _______________ ______________
of electrons.

When a fourth group bonds to the nitrogen, the product is a quaternary

ammonium ion, which has a

__________________________ charge and forms ionic compounds.

• The nitrogen carries a +1 charge.

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 Chapter 10 Lecture Notes

Naming Amines
• To name a 1°, 2°, or 3° amine using IUPAC rules, the parent, the longest chain of carbon
atoms attached to the amine nitrogen atom, is numbered from the end nearer the point of
attachment of the nitrogen.
• The parent chains of amines are named by dropping “e” from the name of the corresponding
hydrocarbon and adding “amine.”
• Write the carbon number of the point of attachment to the nitrogen in front of the parent name.
• CH3CH2CH2NH2 = 1-propanamine

• CH3CHCH3 = 2-propanamine
│
NH2
• If an amine is 2° or 3°, the carbon-containing groups attached to the nitrogen atom that are not
part of the parent chain are substituents and N is used to indicate their location (N-methyl, N,N-
diethyl, etc.).

• Simple amines, those with a relatively few number of carbon atoms, are often identified by
common names by placing “amine” after the names of the groups attached to the nitrogen.
• methylamine = CH3NH2

You Try It!

Match each IUPAC and common name to the correct structural formula:

Practice: Draw the line structure for the following compound, and then name it!

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 Chapter 10 Lecture Notes

• When NH2- group is present as a substituent in a

molecule it is called an ________________group.

• All proteins are made up of

____________________ ________________.

Properties of Amines
• ________________ ____________________on amines can hydrogen bond to water. (water
solubility better than alkanes)

• Primary and secondary amines can hydrogen bond to themselves and each other amines.

– As a result of hydrogen bonding, primary and secondary amines have ________________

______________________ ______________________than alkanes of similar size.

• Volatile amines have strong_______________________.

-Amines smell like rotten fish.

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 Chapter 10 Lecture Notes

• Many amines are physiologically active.

-Smaller amines are irritating to the skin, eyes, and mucous membrane and are toxic
by ingestion.

Heterocyclic Nitrogen Compounds

Rings that contain atoms other than carbon are known as____________________________.

Heterocyclic _______________________ rings are very common in natural compounds found in plants
and animals.

Example (left): DNA

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 Chapter 10 Lecture Notes

Reactions of Amines

1) Reactions of Amines with Water

Amines are _______________________.

• This basic property is due to the electron lone pair on the amine nitrogen that can be used to form
a covalent bond with a H+ ion from water or an acid.

Amines react with water to form ____________________________ _________________________

___________________and OH-.

2) Reactions of Amines with Acid

A ________________ _______ converts an amine into its conjugate acid. (pH<pKa)

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 Chapter 10 Lecture Notes

Amines in Plants: Alkaloids

• __________________are naturally occurring nitrogen compounds isolated from plants.

• Most alkaloids are usually bitter-tasting, physiologically active, and ____________ in high doses.

• Some alkaloids are very familiar, such as the stimulants caffeine and nicotine.

• Other alkaloids are used as pain killers, sleep inducers, and for the creation of euphoria.

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 Chapter 10 Lecture Notes

Amides
Amides result when the –OH from a carboxylic acid is replaced with an –NH2 or an_________________.

Amides contain an –NH2 group with none, one, or both of the N-hydrogens replaced with alkyl
groups (R).
• Examples:

Naming Amides
• Name is based on the longest continuous carbon chain that contains the carbonyl (C=O).
– Just like naming the carboxylic acids!
• Drop the “e” on the parent chain and add “amide”
• List the substituents as usual, making carbonyl-carbon #1
•
• Example:

Name:____________________________

You try one:

Name the compound shown below:

Name:____________________________

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 Chapter 10 Lecture Notes

Formation of Amides
Amides can be made from ___________________________ ____________and _________________.

Examples:

Note that the reaction is_________________________.

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 Chapter 10 Lecture Notes

Stereoisomers
Definition:
• Stereoisomers are molecules that have the same formula and atomic connections, but different
three dimensional shapes.
• We have seen some examples of
stereoisomers in the past:
•
• Geometric isomers (cis and trans)

We will learn about a new class of stereoisomers called _______________________________.

Enantiomers are nonsuperimposable mirror

image molecules.

• The term chiral is used to describe

objects that cannot be superimposed on
their mirror image.
– Example: Your hands are chiral
because your left hand is not
superimposable on your right
hand, its mirror image. (Try it!)

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 Chapter 10 Lecture Notes

A carbon is chiral if it has ________________ different

groups bonded to it!

You Try It! Use an asterisk (*) to label the chiral carbon(s) in each molecule.

• Pairs of enantiomers are identical in almost every way.

• Biological systems such as smell

and taste receptors, enzymes, and
antibodies are selective with respect
to enantiomers.

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 Chapter 10 Lecture Notes

Molecules with More than One Chiral Carbon Atom

As the number of chiral carbon atoms in a molecule increases, so does the number of stereoisomers that
can exist.
Number of stereoisomers = 2n

where n is the number of _______________________ carbon atoms.

You Try It!

a. How many chiral carbon atoms does 2-bromo-3-chlorobutane have?
b. How many stereoisomers are possible for this molecule?

Diastereomers
• Stereoisomers that are not enantiomers (mirror images) are called ______________________.

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