N - Methylaniline - 2: ST ND RD

CHEMISTRY LECTURE OUTLINE
AMINES
- Amines are classified into primary, secondary, or tertiary

- An ALIPHATIC AMINE is one in which all the carbons bonded to nitrogen are derived from alkyl
groups
- An AROMATIC AMINES is one in which one or more of the groups bonded to nitrogen are aryl
groups. Contains a benzene ring
- METHYLAMINE – primary amine
- DIMETHYLAMINE – secondary amine
- TRIMETHYLAMINE – tertiary amine
- ANILINE – 1st aromatic amine (primary)
- N – Methylaniline – 2nd aromatic amine (secondary)
- Benzyldimethylamine – 3rd aliphatic amine (tertiary)
- Heterocyclic amine An amine in which nitrogen is one of the atoms of a ring
- Heterocyclic aromatic amine An amine in which nitrogen is one of the atoms of an aromatic ring
(2 nitrogens)
- Heterocyclic aliphatic amine When the ring is saturated
AMPHETAMINES (PEP PILLS)
- AMPHETAMINES, METHAMPETAMINE, PHENTERMINE – all synthetic amines, and are powerful

stimulants of the nervous system
- The sulfate salt of AMPHETAMINE is named BENZEDRINE
- The hydrochloride salt of the S enantiomer of METHAMPETHAMINE e is named METHEDRINE
- the hydrochloride salt of PHENTERMINE is named FASTIN
- Abuse of amphetamines can have severe effects on both body and mind. They are addictive,
concentrate in the brain and nervous system, and can lead to long periods of sleeplessness, loss
of weight, and paranoia.
ALKALOIDS
- ALKALOIDS are basic nitrogen-containing compounds found in the roots, bark, leaves, berries, or
fruits of plants
- ALKALOIDS – was chosen because these compounds are alkali like ( term for basic substance)
- (S)-Coniine is the toxic principle of water hemlock (a member of the carrot family) Its ingestion
can cause weakness, labored respiration, paralysis, and eventually death
- (S) – nicotine – occurs in tobacco plants
PHYSICAL PROPERTIES OF AMINES
- LOW MOLECULAR WEIGHT AMINES – have very sharp and penetrating odors
- Amines are polar compounds because of the difference in electronegativity between nitrogen
and hydrogen (3.0 - 2.1 = 0.9).
- Both primary and secondary amines have N - H bonds
- TERTIARY AMINES – doesn’t have a hydrogen bond
TRANQUILIZERS
- TRANQUILIZERS – a drug that provides relief from the symptoms of anxiety and tension
- BEBNZODIAZEPINE – the first modern tranquilizers
- CHLORODIAZEPOXIDE – came after benzodiazepine
- DIAZEPAM – came after chlorodiazapoxide
EPINEPHRINE
- Epinephrine was first isolated in pure form in 1897 and its structure determined in 1901
- Epinephrine is a vasoconstrictor, a bronchodilator, and a cardiac stimulant. Can be a remedy for
asthma
- (R)-Isoproterenol was introduced into clinical medicine in 1951; for the next two decades, it
was the drug of choice for the treatment of asthmatic attacks
NOMENCLATURE
- IUPAC names for aliphatic amines are derived just as they are for alcohols. The final -e of the
parent alkane is dropped and replaced by –amine and –azane for suffixes. Azanyl- and
amino- prefixes.
- AMINO group that is bonded to BENZENE RING is called aniline
- ALKYL groups attached to an AMINE should be named with N,N
- ORTHO – 2 carbons away from each other
- META - 3 carbons away from each other
- PARA - 4 carbons away from each other
- ALIPHATIC AMINES – bonded by an alkyl group with an ending suffix of –amine (Ex. Ethylamine,
trimethylamine)
- COMMON NAMES – are numbered using greek letter (alpha, beta, gamma, delta, epsilon …)
- IUPAC NAMES – are numbered using numbers (1, 2, 3, 4 ,5 …)
SUMMARY OF KEY REACTIONS
- BASICITY OF ALIPHATIC AMINES

- BASICITY OF AROMATIC AMINES
- REACTIONS WITH ACID
ALDEHYDES AND KETONES
- CARBONYL GROUP – aldehydes, ketones, carbohydrates and carboxylic acid.
NOMENCLATURE
- To name an IUPAC ALDEHYDE, we change the suffix -e of the parent alkane to –al or retain the
suffix –e then add -carbaldehyde
- The carbonyl group of an aldehyde can appear only at the end of a parent chain and numbering
must start with it as carbon 1, there is no need to use a number to locate the aldehyde group.
- UNSATURATED ALDEHYDES, we show the presence of the carbon– carbon double bond and the
aldehyde by changing the ending of the parent alkane from -ane to -enal:
- “-en-” to show the carbon–carbon double bond, and “-al” to show the aldehyde
PHYSICAL PROPERTIES OF ALDEHYDES AND KETONES
- Oxygen is more electronegative than carbon. Therefore a carbon–oxygen double bond is POLAR
- Most aldehydes and ketones have strong odors
- The odors of ketones are generally
- pleasant, and many are used in perfumes and as flavoring agents
- The odors of aldehydes vary
OXIDATION
- In oxidation an aldehyde will form into a carboxylic acid

- If it can be oxidized, it is an aldehyde; otherwise, it is a ketone
REDUCTION
- Aldehydes are reduced to primary alcohols

- Ketones are reduced to secondary alcohols
- The reduction of a C - O double bond under these conditions is slower than the reduction of a
C- C double bond
ADDITION
- Addition of a molecule of alcohol to the carbonyl group of an aldehyde or ketone forms a

hemiacetal (a half-acetal).
- hemiacetal is a carbon bonded to one -OH group and one –OR
- Hemiacetals are generally unstable and are only minor components of an equilibrium mixture
KET0-ENOL TAUTOMERISM
- Keto and enol forms are examples of tautomers

- Keto is simply a ketone that is attached to a carbon
- Enol is an alcohol with a double bond
CARBOXYLIC ACID
- The functional group of a carboxylic acid is a carboxyl group

- can be written as COOH CO2H and (structural formula)
NOMENCLATURE
- Drop the final -e from the name of the parent alkane and replace it by -oic acid. Or just add a
prefix –carboxylic acid to an alkane.
- When a carboxylic acid also contains an -OH (hydroxyl) group, we indicate its presence by
adding the prefix hydroxy-.
PHYSICAL PROPERTIES OF CARBOXYLIC ACIDS
- Carboxylic acids have significantly higher boiling points than other types of organic compounds
- higher boiling points result from their polarity
- Carboxylic acids are more soluble in water than are alcohols, ethers, aldehydes, and ketones of
comparable molecular weight
- The first four aliphatic carboxylic acids (formic, acetic, propanoic, and butanoic) are infinitely
soluble in water
- Butanoic acid is found in stale perspiration and is a major component of “locker room odor.”
- Carboxylic acids doesn’t have a pleasant odors. Second, carboxylic acids have a characteristic
sour taste
WHAT ARE SOAPS AND DETERGENT?
- FATTY ACIDS – are long unbranched carboxylic acids, consisting of 12 to 20 carbons.

- Derived from the hydrolysis of animal fats, vegetable oils, or the phospholipids.
- CHARACTERISTIC OF A FATTY ACID
 Nearly all fatty acids have an even number of carbon atoms, most between 12 and 20, in an
unbranched chain.
 The three most abundant fatty acids in nature are palmitic acid, stearic acid, and oleic acid.
 In most unsaturated fatty acids, the cis isomer predominates; the trans isomer is rare.
 Unsaturated fatty acids has a lower melting point than the saturated fatty acid.
 GREATER UNSATURATION – lower boiling point
 SATURATED FATTY ACIDS – are solid at room temperature
 UNSATURATED FATTY ACIDS – has at least 1 double bond
TRANS FATTY ACIDS
- FATS - are added to processed foods to provide a desirable firmness along with a moist texture
and pleasant taste
- Recent studies have shown that consuming significant amounts of trans fatty acids can lead to
serious health problems
- OMEGA – 3 acid is known to be a healthy fatty acid.
- Eicosapentaenoic acid, C20H30O2, is an important fatty acid in the marine food chain and serves
as a precursor in humans
- Docosahexaenoic acid, C22H32O2, is found in fish oils and many phospholipids
STRUCTURE AND PREPARATION OF SOAPS
- Natural soaps are most commonly prepared from a blend of tallow and coconut oils.
- The reaction that takes place is called saponification
- nonpolar organic grease, oil, and fat are “dissolved” and washed away in the polar wash water
REACTIONS OF CARBOXYLIC ACIDS
- ACIDITY – donates hydrogen

- BASICITY – receives hydrogen
- REDUCTION –
- FISCHER ESTERIFICATION – making an ester, type of a condensation reaction, carboxylic acid +
alcohol = ester + water
- DECARBOXYLATION -

N - Methylaniline - 2: ST ND RD

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CHEMISTRY LECTURE OUTLINE

- Amines are classified into primary, secondary, or tertiary

AMPHETAMINES (PEP PILLS)

- AMPHETAMINES, METHAMPETAMINE, PHENTERMINE – all synthetic amines, and are powerful

PHYSICAL PROPERTIES OF AMINES

SUMMARY OF KEY REACTIONS

- BASICITY OF ALIPHATIC AMINES

ALDEHYDES AND KETONES

- CARBONYL GROUP – aldehydes, ketones, carbohydrates and carboxylic acid.

- In oxidation an aldehyde will form into a carboxylic acid

- Aldehydes are reduced to primary alcohols

- Addition of a molecule of alcohol to the carbonyl group of an aldehyde or ketone forms a

- Keto and enol forms are examples of tautomers

- The functional group of a carboxylic acid is a carboxyl group

PHYSICAL PROPERTIES OF CARBOXYLIC ACIDS

WHAT ARE SOAPS AND DETERGENT?

- FATTY ACIDS – are long unbranched carboxylic acids, consisting of 12 to 20 carbons.

TRANS FATTY ACIDS

STRUCTURE AND PREPARATION OF SOAPS

REACTIONS OF CARBOXYLIC ACIDS

- ACIDITY – donates hydrogen

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