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CARBOXYLIC ACIDS, AMINES, THIOLS
CARBOXYLIC ACIDS
IUPAC naming system
A carboxylic acid contains a –COOH
functional group (carboxyl). This
group must be included in the main C-
chain that is named as carbon #1.
CARBOXYLIC ACIDS
The “e” of –ane, –ene and –yne endings
is replaced with –oic acid.
HCOOH
CH3COOH
CH3CH2COOH
methanoic acid
ethanoic acid
propanoic acid
CARBOXYLIC ACIDS
Common naming system
The prefix used with aldehydes may
also be used with carboxylic acids. In
this case an –ic acid is the suffix.
HCOOH
CH3COOH
CH3CH2COOH
formic acid
acetic acid
proprionic acid
CARBOXYLIC ACIDS
Example #1Example #1
a) What is the structural formula for
propenoic acid?
b) What is the IUPAC name for the
following acid?
CH2-CH-COOH
CH3 CH3
OH
O
2-methylbutanoic acid
CARBOXYLIC ACIDS
Properties of Carboxylic AcidsProperties of Carboxylic Acids
Carboxylic acids have higher boiling points
than their corresponding hydrocarbon.
Carboxylic acids have similar solubility
properties as their corresponding alcohol.
All carboxylic acids have acidic properties.
CARBOXYLIC ACIDS
AMINES
All amines are essentially derived from NH3.
Depending on the number of carbon side-
chains off of the N, we can form different
types of amines.
primary amine secondary amine tertiary amine
AMINES
IUPAC naming system
This system adds the suffix “amine” to the end
of the name.
butan-1-amine
propan-2-amine
H2N
H2N
AMINES
IUPAC naming system
When there is more than one amine group
present, keep the “e” ending of the C-chain
root.
butane-1,2-diamine
hexane-2,3,4-triamine
AMINES
H2N
NH2
NH2 NH2
NH2
IUPAC naming system
If there are carbon side-chains off of the N-
group, it is denoted by an “N-” prefix.
N-methylbutan-1-amine
N,N-dimethylmethananime
N
H
NH3C CH3
CH3
AMINES
IUPAC naming system
The N-group is treated as a side-chain and is
added as a prefix on the C-chain root if a
group with a higher priority is present.
AMINES
NH2
OH
3-aminobutan-2-ol 5-amino-3-hydroxy-2-oxohexanal
O
OH
O
NH2
Example #2Example #2
Write the IUPAC name for the following
molecule.
CH3 – N – CH3
CH3CHCH3
N,N-dimethylpropan-2-amine
AMINES
Example #3Example #3
Draw a 1°, 2° and 3° amine which each contain a
total of three carbons.
NH3C CH3
CH3
NCH3CH2 H
CH3
NCH3CH2CH2 H
H
primary secondary
tertiary
AMINES
Properties of AminesProperties of Amines
Amines have higher boiling points than their
hydrocarbon counterparts.
Smaller amines are more soluble in water than
larger amines.
For mp and bp of amines of the same size,
3° < 2° < 1°
In general, amines are basic in nature.
AMINES
THIOLS
THIOLS
Properties of thiolsProperties of thiols
Contains the sulfhydryl group (-SH)
Strong odours
IUPAC naming system
Suffix ‘thiol’ is added to the end of the hydrocarbon
group
Example:
THIOLS
methanethiol

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Tang 07 carboxylic acids, amines, &amp; thiols 2015

  • 3. IUPAC naming system A carboxylic acid contains a –COOH functional group (carboxyl). This group must be included in the main C- chain that is named as carbon #1. CARBOXYLIC ACIDS
  • 4. The “e” of –ane, –ene and –yne endings is replaced with –oic acid. HCOOH CH3COOH CH3CH2COOH methanoic acid ethanoic acid propanoic acid CARBOXYLIC ACIDS
  • 5. Common naming system The prefix used with aldehydes may also be used with carboxylic acids. In this case an –ic acid is the suffix. HCOOH CH3COOH CH3CH2COOH formic acid acetic acid proprionic acid CARBOXYLIC ACIDS
  • 6. Example #1Example #1 a) What is the structural formula for propenoic acid? b) What is the IUPAC name for the following acid? CH2-CH-COOH CH3 CH3 OH O 2-methylbutanoic acid CARBOXYLIC ACIDS
  • 7. Properties of Carboxylic AcidsProperties of Carboxylic Acids Carboxylic acids have higher boiling points than their corresponding hydrocarbon. Carboxylic acids have similar solubility properties as their corresponding alcohol. All carboxylic acids have acidic properties. CARBOXYLIC ACIDS
  • 9. All amines are essentially derived from NH3. Depending on the number of carbon side- chains off of the N, we can form different types of amines. primary amine secondary amine tertiary amine AMINES
  • 10. IUPAC naming system This system adds the suffix “amine” to the end of the name. butan-1-amine propan-2-amine H2N H2N AMINES
  • 11. IUPAC naming system When there is more than one amine group present, keep the “e” ending of the C-chain root. butane-1,2-diamine hexane-2,3,4-triamine AMINES H2N NH2 NH2 NH2 NH2
  • 12. IUPAC naming system If there are carbon side-chains off of the N- group, it is denoted by an “N-” prefix. N-methylbutan-1-amine N,N-dimethylmethananime N H NH3C CH3 CH3 AMINES
  • 13. IUPAC naming system The N-group is treated as a side-chain and is added as a prefix on the C-chain root if a group with a higher priority is present. AMINES NH2 OH 3-aminobutan-2-ol 5-amino-3-hydroxy-2-oxohexanal O OH O NH2
  • 14. Example #2Example #2 Write the IUPAC name for the following molecule. CH3 – N – CH3 CH3CHCH3 N,N-dimethylpropan-2-amine AMINES
  • 15. Example #3Example #3 Draw a 1°, 2° and 3° amine which each contain a total of three carbons. NH3C CH3 CH3 NCH3CH2 H CH3 NCH3CH2CH2 H H primary secondary tertiary AMINES
  • 16. Properties of AminesProperties of Amines Amines have higher boiling points than their hydrocarbon counterparts. Smaller amines are more soluble in water than larger amines. For mp and bp of amines of the same size, 3° < 2° < 1° In general, amines are basic in nature. AMINES
  • 18. THIOLS Properties of thiolsProperties of thiols Contains the sulfhydryl group (-SH) Strong odours
  • 19. IUPAC naming system Suffix ‘thiol’ is added to the end of the hydrocarbon group Example: THIOLS methanethiol