Oxygen-Containing Hydrocarbon Derivatives

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ethanol

ALCOHOLS
•Derivatives that contain the
hydroxyl group
CLASSES OF ALCOHOLS ACCORDING TO THE CARBON THAT BEARS THE
HYDROXYL GROUP

primary
• RCH2OH

Secondary
• R2CHOH

tertiary
• R3COH
primary tertiary

tertiary secondary
HOW ARE ALCOHOLS NAMED?

The root
name is
based on • The chain is numbered so as to give
the longest the alcohol unit the lowest possible
chain with number.
the –OH
attached.
• The alcohol suffix is appended after
–ane + -ol
the hydrocarbon suffix minus the
= -anol
“e.”
2-methylbutan-1-ol pentan-3-ol

2-methylbutan-2-ol 3-ethylhexan-2-ol
2,2-dimethylpropan-1-ol 1-methylcyclohexan-1-ol

3-ethylpentan-3-ol butan-2-ol
(E)-2-methylhepta-4,6-dien-3-ol 2,4-dimethylpent-3-en-1-ol

penta-1,2,3-triol propane-1,2,3-triol
Name the following alcohols and classify as to whether they are
primary, secondary, or tertiary?
ETHERS
• Organic derivatives of water that have two
organic groups bonded to the same oxygen atom
Simple ethers
Ethyl methyl ether

•If both groups are simple alkyl


groups, then the ether is named as
an alkyl alkyl ether.
•The alkyl groups are listed in diethyl ether

alphabetical order.
•If the two alkyl groups are the
same, then it is a dialkyl ether
Ethyl propyl ether
Intermediate ethers
• If one of the groups is more
complex, then the ether group is
usually treated as an alkoxy (i.e. R-
O) substituent.
• The more complex group (i.e.
longer chain, more branched, other 2-methoxypropane
substituents) defines the root.
complex ethers
3-oxaheptane
•If both groups are
complex then the
ether can be named
using –oxa.
Name the following ethers.
4-ethoxyoctane butyl methyl ether
or or
4-propyl-3-oxaoctane 1-methoxybutane
or

2-oxahexane

methoxycyclohexane 2-isopropoxypropane or
or cyclohexyl methyl ether 2,4-dimethyl-3-oxapentane

or

diisopropyl ether
PHENOLS
• Aromatic compounds with the hydroxyl
functional group
HOW ARE PHENOLS NAMED?

PHENOLS
• The prefixes ortho-, meta, and para
are named
can be used to designate the relative
like other
positions of the the two substituents
aromatic
for disubstituted compounds.
compounds.
-phenol is
used as the
parent • Numbering from the -OH to give the
name substituent/s the lowest locant
instead of
benzene
Name the following phenols.

2-chlorophenol o-nitrophenol
or

ortho-chlorophenol

4-chloro-3,5-dimethylphenol

2,4-dibromophenol
ALDEHYDES AND KETONES
• Organic compounds that contain the carbonyl functional
group
methanal (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-
AKA 1-en-1-yl)nona-2,4,6,8-tetraenal AKA
formaldehyde
retinal

ALDEHYDES
• Organic compounds that contain the carbonyl functional
group
HOW ARE ALDEHYDES NAMED?

The root name is based on the longest chain containing the


carbonyl group.
Since the carbonyl group is at the end of the chain,
it must be C1.

-ane + -al = anal, -ene + -al = enal


Name the following aldehydes.
ethanal propanal

butanal pentanal
Name the following aldehydes.
2-ethyl-4-methylpentanal 2,2-dimethylbutanal

propenal 3-bromobutanal
HOW ARE CYCLIC AND AROMATIC ALDEHYDES NAMED?

For cyclic aldehydes in which the –CHO group is directly attached to a


ring, the suffix –carbaldehyde is used

For cyclic aldehydes in which the –CHO group is directly attached to a ring,
the suffix –carbaldehyde is used.

-ane + al = anal, -ene + al = enal

For aromatic aldehydes, benzaldehyde is used as the parent.


Name the following aldehydes.
cyclohexanecarbaldehyde benzaldehyde

4-bromobenzaldehyde 2,5-dimethylbenzaldehyde
Propan-2-one acetophenone benzophenone

AKA
acetone

KETONES
• Organic compounds that contain the carbonyl functional
group
HOW ARE KETONES NAMED?

The root named is based on the longest chain containing the


carbonyl group.
The chain is numbered so as to give the ketone
carbonyl the lowest possible number.

-ane + -one = anone, -ene + -one = enone


Name the following ketones
hexan-3-one pentan-3-one

Hexane-2,4-dione
hex-4-en-2-one
Name the following ketones.
3,6,6-trimethylheptan-2-one 4-bromo-2-methylheptan-3-one

5-(1,1-dimethylethyl)nonan-2-one
3,3-dimethylcyclopentan-1-one
or

5-(tert-butyl)nonan-2-one
QUIZ 2. Name the following oxygen-containing derivatives.

2 3

4 5
hexanoic acid
Acetic acid

cholic acid

CARBOXYLIC ACIDS
• RCO2H
HOW ARE CARBOXYLIC ACIDS NAMED?

The root named is based on the longest chain containing the


carboxyl group.
Since the carboxyl group is at the end of the chain,
it must be C1.

-ane – e + -oic acid = -anoic acid, -ene – e + -oic acid = enoic


acid
Name the following carboxylic acids.
Ethanoic acid propanoic acid
or

acetic acid

butanoic acid pentanoic acid


Name the following carboxylic acids.
3-methylhexanoic acid cyclohexanecarboxylic acid

6-chloro-4-ethyl-2-methyloctanoic acid (Z)-2-ethyl-3-isopropyl-4-methyloct-3-enoic acid


CARBOXYLIC ACIDS
• RCO2H
isopentyl valerate
methyl acrylate

ESTERS
• Alkyl derivatives of carboxylic acids
• RCOOR’
HOW ARE ESTERS NAMED?

An ester has two parts to its structure, each of


which must be named: an acyl group (RCO – )
and an alkyl group (designated as R') bonded
to an oxygen atom.

In the IUPAC system, esters


are identified by the suffix -
ate.
Name the following esters.

methyl propanoate propyl methanoate

ethyl butanoate butyl ethanoate


Name the following esters.

methyl propanoate propyl 2-methylbutanoate

cyclopropyl pentanoate cyclohexyl 2-isopropylpentanoate


Name the following esters.

ethyl 3,6-dimethyloctanoate methyl 2-ethylpentanoate

ethyl benzoate

cyclopentyl
cyclohexanecarboxylate
adipoyl chloride
phosgene

ACID HALIDES
• derivatives of carboxylic acids
• where X = Cl, Br are the most common
HOW ARE ACID HALIDES NAMED?

Acyl or acid halides are derivatives of carboxylic acids.

The root name is based on the longest chain including the carbonyl group of the acyl group.

Since the acyl group is at the end of the chain, the C=O carbon must be C1.

The acyl halide is appended after the hydrocarbon suffix minus the “e”.
• e.g. –ane + -oyl chloride = -anoyl chloride

The most common halide encountered is the chloride, hence acyl or acid chlorides.
Name the following acid halides.
ethanoyl chloride propanoyl chloride

butanoyl chloride pentanoyl chloride


Name the following acid halides.

2,2-dimethylbutanoyl chloride 2,6-dimethylheptanoyl chloride

benzoyl chloride 2,4-dimethylhexanoyl chloride


ANHYDRIDES
• Derivatives of carboxylic acids
• Contain two carbonyl groups joined by a single oxygen atom
ANHYDRIDES
• may be symmetrical, mixed, or cyclic
HOW ARE ANHYDRIDES NAMED?
Name the following anhydrides.

propanoic anhydride butanoic anhydride

pentanoic anhydride hexanoic anhydride


Name the following anhydrides.

pentanoic propanoic anhydride acetic cyclohexanecarboxylic anhydride

hexanoic propionic anhydride 2,3-dimethylbutanoic anhydride


Glutathione

AMIDES
• derivatives of carboxylic acids
HOW ARE AMIDES NAMED?
Name the following amides.

acetamide propanamide

butanamide pentanamide
Name the following amides.

N-ethylpropanamide N-ethyl-N-methylacetamide

benzamide N-cyclopentylbenzamide

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