Understanding Carbon Compounds in Chemistry
Understanding Carbon Compounds in Chemistry
Carbon
Compounds
Lesson Outline:
• The Uniqueness of
Carbon
Carbon • Hydrocarbons
• Aliphatic Hydrocarbons
Compounds • Aromatic Hydrocarbons
• Functional Groups
1. The Uniqueness of Carbon
Organic Chemistry
1. The Uniqueness of Carbon
Organic Chemistry
1. The Uniqueness of Carbon
Organic Chemistry
1. The Uniqueness of Carbon
Organic Chemistry
Methane, CH4
3-chloro-1-butene
Organic Chemistry
1. Hydrocarbons: Saturated hydrocarbons
Organic Chemistry
1. Hydrocarbons: Saturated hydrocarbons Methane, CH4
Hexane, C6H14
Organic Chemistry
1. Hydrocarbons: Saturated hydrocarbons Methane, CH4
Organic Chemistry
1. Hydrocarbons: Unsaturated hydrocarbons
Ethene, C2H4
Organic Chemistry
1. Hydrocarbons
Different representations of
propyne
Organic Chemistry
1. Hydrocarbons: Unsaturated Hydrocarbons
Cyclopentane and cyclohexane
• Cycloalkanes are hydrocarbons containing one or
more carbon rings to which hydrogen atoms are
attached.
• The general formula for a saturated hydrocarbon
containing one ring is CnH2n.
• Bicycloalkanes are two cycloalkanes connected
by central carbon atoms.
Organic Chemistry
2. Hydrocarbons
Organic Chemistry
2. Hydrocarbons
Organic Chemistry
2. Hydrocarbons
Organic Chemistry
3. Alkanes: Saturated hydrocarbons
Organic Chemistry
3. Alkanes: Saturated hydrocarbons
The tetrahedral
methane molecule
Organic Chemistry
3. Alkanes: Saturated hydrocarbons Greek prefixes in red
Alkyl group: Alkane
minus one hydrogen
Methyl
• Methane (CH4), ethane (C2H6), and propane Ethyl
(C3H8) are the beginning of a series of Propyl
compounds in which any two members in a Butyl
sequence differ by one carbon atom and two
Pentyl
hydrogen atoms- namely a CH2 unit.
Hexyl
• The first 10 members of alkanes series are Heptyl
the following: Octyl
Nonyl
Decyl
Organic Chemistry
4. Alkenes and Alkynes
Organic Chemistry
4. Alkenes and Alkynes
propene
Organic Chemistry
4. Alkenes and Alkynes
CH2=CHCH3 is propene.
Organic Chemistry
4. Alkenes and Alkynes
Organic Chemistry
4. Alkenes and Alkynes
4-chloro-2-pentene
Organic Chemistry
4. Alkenes and Alkynes
Organic Chemistry
4. Alkenes and Alkynes
Organic Chemistry
4. Alkenes and Alkynes
Organic Chemistry
4. Alkenes and Alkynes
Organic Chemistry
4. Alkenes and Alkynes
1. 3-methyl-2-pentene
2. Cyclohexyne
3. 2,3-dibromo-5,5,6-trimethyl-1-octene
Organic Chemistry
4. Alkenes and Alkynes
Organic Chemistry
5. Hydrocarbon Reactions
Organic Chemistry
5. Hydrocarbon Reactions
Organic Chemistry
5. Hydrocarbon Reactions
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5. Hydrocarbon Reactions
+ → +
Organic Chemistry
6. Aromatic Hydrocarbons
Organic Chemistry
6. Aromatic Hydrocarbons O-dichlorobenzene
Organic Chemistry
6. Aromatic Hydrocarbons
Organic Chemistry
6. Aromatic Hydrocarbons
Organic Chemistry
6. Functional Groups
Organic Chemistry
6. Functional Groups: Alcohols
Organic Chemistry
6. Functional Groups: Alcohols
alcohols.
Organic Chemistry
6. Functional Groups: Alcohols Methyl alcohol
butyl alcohol
Organic Chemistry
6. Functional Groups: Alcohols
Organic Chemistry
6. Functional Groups: Alcohols
alkanes.
Organic Chemistry
6. Functional Groups: Alcohols
3,4,4-heptanetriol
Organic Chemistry
6. Functional Groups: Alcohols
Organic Chemistry
6. Functional Groups: Alcohols
1,2-propanediol
1-methylcyclopentanol
Organic Chemistry
6. Functional Groups: Alcohols
Organic Chemistry
6. Functional Groups: Alcohols
Organic Chemistry
6. Functional Groups: Classification
of Alcohols
• Some of the properties of alcohols depend on
the number of carbon atoms attached to the
specific carbon atom that is attached to the
OH group.
1. A primary (1o) alcohol is one in which the
carbon atom with the OH group is attached
to one other carbon atom. Its general
formula is RCH2OH. 1-butanol is a primary
alcohol, or isobutyl alcohol,
C3H7CH2OH
Organic Chemistry
6. Functional Groups: Classification
of Alcohols
• Some of the properties of alcohols depend on
the number of carbon atoms attached to the sec-propyl
alcohol,
specific carbon atom that is attached to the (CH3)2CHOH
OH group.
2. A secondary (2o) alcohol is one in which the
carbon atom with the OH group is attached to
two other carbon atoms. Its general formula is
R2CHOH. sec-pentyl alcohol,
(C2H5)2CHOH
Organic Chemistry
6. Functional Groups: Classification
of Alcohols
• Some of the properties of alcohols depend on
the number of carbon atoms attached to the
specific carbon atom that is attached to the
OH group.
3. A tertiary (3o) alcohol is one in which the
carbon atom with the OH group is attached to
three other carbon atoms. Its general formula is
R3COH. Isobutyl alcohol,
(CH3)3COH
Organic Chemistry
6. Functional Groups: Classification
of Alcohols
• The prefixes Iso-, Sec- and Tert- reflects the
classification of an alcohol.
• Examine the structural formula of isobutyl,
Sec-butyl, and Tert-butyl alcohols:
CN: Isobutyl alcohol CN: Sec-butyl alcohol CN: Tert- butyl alcohol
IUPAC: 2-methyl-1-propanol IUPAC: 2-butanol IUPAC: 2-methyl-2-propanol
Organic Chemistry
6. Functional Groups: Classification
of Alcohols
• Sample Problems: name and classify the
following alcohols:
Organic Chemistry
6. Functional Groups: Classification
of Alcohols
• Sample Problems: name and classify the
following alcohols:
Class: Secondary
Common name: cyclohexyl alcohol
IUPAC: cyclohexanol
Organic Chemistry
6. Functional Groups: Classification
of Alcohols
• Sample Problems: Draw the structures of the following
alcohols.
3- heptanol 3-methyl-2-pentanol
Organic Chemistry
6. Functional Groups: Classification
of Alcohols
• Sample Problems: Draw the structures of the following
alcohols.
3- heptanol 3-methyl-2-pentanol
Organic Chemistry
6. Functional Groups: Reactions of
Alcohols
• Chemical reactions in
alcohols occur mainly at the
functional group, but some
involve hydrogen atoms
Concd H2SO4, 180oC
attached to OH-bearing Excess acid +
carbon atom or to an
adjacent carbon atom.
• The two most common
reactions of alcohols are
dehydration and oxidation.
Organic Chemistry
6. Functional Groups: Reactions of
Alcohols
• An alcohol undergoes
dehydration in the presence of
a catalyst to form an alkene
and water.
Concd H2SO4, 180oC
• The reaction removes OH Excess acid +
group from the carbon atom
and a hydrogen atom from an
adjacent carbon atom in the
same molecule.
• Observe the formation of
ethylene and water from
ethanol.
Organic Chemistry
6. Functional Groups: Reactions of
Alcohols
• Under proper conditions, it is possible for dehydration to occur between two
alcohol molecules. The entire OH group of one molecule and the only hydrogen
atom of the OH group of the second molecule are removed.
• The two ethyl groups attached to an oxygen atom to form an ether molecule.
• Observe the formation of diethyl ether and water from two molecules of ethanol:
Concd H2SO4
Organic Chemistry
6. Functional Groups: Reactions of
Alcohols
• Primary and secondary alcohols are readily
oxidized.
• The oxidation of ethanol to form acetaldehyde
(an aldehyde) is described in the equation:
[O]
Organic Chemistry
6. Functional Groups: Reactions of
Alcohols
• Secondary alcohols are oxidized to form
ketones. The equation on the side shows the
oxidation of isopropyl alcohol to form
acetone, a ketone:
K2Cr2O7
H+
[O]
No reaction
A tertiary alcohol
Organic Chemistry
6. Functional Groups: Reactions of
Alcohols
• Sample Problems: Write the equation for the
oxidation of each alcohol. Use [O] above the
arrow to indicate an oxidizing agent. If no
reaction occurs, write “no reaction”.
Organic Chemistry
6. Functional Groups: Reactions of
Alcohols
• Sample Problems: Write the equation for the
oxidation of each alcohol. Use [O] above the
arrow to indicate an oxidizing agent. If no
reaction occurs, write “no reaction”.
[O]
Carbonyl group
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
• In a ketone, two carbon groups are attached
to the carbonyl carbon atom.
• The following general formulas, in which R
represents an alkyl group and Ar stands for an
aryl group, represent ketones:
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
• In an aldehyde, at least one of the attached
groups must be a hydrogen atom. The
following compounds are aldehydes:
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
• In condensed formulas, we use –CHO- to
identify an aldehyde rather than COH, which
might be confused with alcohol. A ketone is
also represented by -CO-.
• Because aldehydes and ketones contain the
same functional group, they share many
common properties.
Organic Chemistry
formaldehyde
6. Functional Groups: Aldehydes
and Ketones
• The common names of aldehydes are taken
acetaldehyde
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
• Because the carbonyl group in ketone must be
attached to two carbon groups, the simplest
ketone has three carbon groups. It is widely
known as acetone, a unique name unrelated
to other common names for ketones.
CN: acetone
IUPAC: dimethyl ketone
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
• Common naming for ketones and aldehydes:
• Generally, the common names of ketones CN: acetone
consist of the names of the groups attached o
the carbonyl group, followed by the word
ketone.
• Another name for acetone, then, is dimethyl
ketone.
• The ketone with four carbon atoms is ethyl
methyl ketone.
ethyl methyl ketone
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
• Sample Problems: Classify the following as
an aldehyde or as a ketone. Give the common
name of each ketone.
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
• Sample Problems: Classify the following as
an aldehyde or as a ketone. Give the common
name of each ketone.
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
• IUPAC rules in naming for ketones and
aldehydes:
1. The stem of aldehydes and ketones are
derived from those of the parent alkanes,
defined by the longest continuous chain
(LCC).
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
2. For an aldehyde, drop the –e from the alkane IUPAC: methanal
IUPAC: propanal
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
• IUPAC rules in naming for ketones and
aldehydes: IUPAC: propanone
IUPAC: butanone
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
• IUPAC rules in naming for ketones and
aldehydes:
4. To indicate the position of a substituent on an
aldehyde, the carbonyl carbon is always
considered C1: it is unnecessary to designate
this group by number.
3-bromopentanal
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
5. To indicate the position of a substituent on
ketone, number the chain in the manner that
gives the carbinyl carbon atom the lowest
possible number. In cyclic ketones, it is
understood that the carbonyl carbon atom is
C1.
IUPAC4,5- dibromo-3-heptanone
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
• Sample Problems. Give the IUPAC name for
each compound:
Organic Chemistry
6. Functional Groups: Aldehydes
and Ketones
• Sample Problems. Give the IUPAC name for
each compound:
2-methylpentanal 2,4-dimethyl-3-pentanone
group.
Organic Chemistry
6. Functional Groups: Carboxylic
Acids, Amides, Nitriles, and Esters
• In amides, the carbonyl carbon is bonded to a
nitrogen.
• The nitrogen in an amide can be bonded to
either hydrogens, to carbons, or to both.
Organic Chemistry
6. Functional Groups: Carboxylic
Acids, Amides, Nitriles, and Esters
• In esters, the carbonyl group is bonded to an
oxygen which itself is bonded to another
carbon.
• Thioesters are similar to esters, except a
sulfur is in place of the oxygen.
Organic Chemistry
6. Functional Groups: Carboxylic
Acids, Amides, Nitriles, and Esters
• The nitrile group, a carbon is triple bonded to
a nitrogen. Nitriles are also often referred ti
as cyano group.
Organic Chemistry
6. Functional Groups: Ethers
Organic Chemistry
6. Functional Groups: Ethers
1.
2.
Organic Chemistry
6. Functional Groups: Ethers
1. Dipropyl ether
Organic Chemistry
6. Functional Groups: Ethers
1. Dipropyl ether
Organic Chemistry
End of the Chapter.