Gen - Chem Module 3 PDF

Module 3
ALKANES, ALKENES, ALKYNES
ALKANES: SATURATED HYDROCARBON

Saturated: C—C bonds are all single bonds
Isomerism in Alkanes
• Structural isomerism- occurs when two molecules have the same
atoms but different bonds.
o Butane and all succeeding members if the alkanes exhibit
structural isomerism
o
RULES IN NAMING ALKANES:

Suppose the root alkane name follows the location and name. Substituents in alphabetical order and
use di-, tri-, tetra-, penta-, etc.
Example:
Cyclic Alkanes
• Carbon atoms can form rings containing
only C—C single bonds
• Formula CnH2n
ALKENES ALKYNES
THE NAMING OF ALKENES AND ALKYNES

ALKENES
• Root hydrocarbon name ends in -ene
• If there are more than three carbons, the double bond is indicated by the lowest-numbered
carbon atom in the bond.
ALKYNES
• Root hydrocarbon ends in -yne
• If there are more than three carbons, the double bond is indicated by the lowest-numbered
carbon atom in the bond.
CHEMICAL REACTION OF ALKENES AND ALKYNES

HYDROGENATION- adding a hydrogen atom to the alkenes/ alkynes to produce alkanes. Pi bonds
(which are weaker than a C—C bonds), are broken, and new sigma bonds are formed to the sigma
atoms being added
HALOGENATION- addition of halogen atoms of alkenes and alkynes

AROMATIC HYDROCARBONS
• A special class of cyclic unsaturated hydrocarbons.
• Simplest of these is Benzene (C6H6)
• The delocalization of the 𝜋 electrons makes benzene ring behave differently from a typical
unsaturated hydrocarbon
GEOMETRIC ISOMERISM IN AROMATICS

Ortho (o-) = two adjacent substituents
o-dichlorobenzene
meta (m-)= one carbon is between the substituents

m-dichlorobenzene
para (p-)= two carbons between substituents

p-dichlorobenzene
ALCOHOLS AND PHENOLS
Alcohols and Phenols can be thought of as organic derivatives of water in which an organic
compound replaces one of the waters hydrogens:
H—O—H versus R—O—H and Ar—O—H
Note: R is rest of the molecules/ atoms
Ar -aryl group or the aromatic hydrocarbon
• Alcohols occur widely in nature and have many industrial and pharmaceutical applications.
Methanol, for instance is one of the most important of all industrial chemicals. Historically,
methanol was prepared by heating wood in the absence of air and thus came to be called
wood alcohol. Methanol is prepared by catalytic reduction of carbon monoxide with hydrogen
gas.
• Methanol is toxic to humans, causing blindness in small doses and death in larger amounts.
Industrially, it is used both as a solvent and as a starting material for producing formaldehyde
(CH2O) and acetic acid (CH3COOH).
• Ethanol was one of the first organic chemicals to be prepared and purified.
• Ethanol for industrial uses as a solvent or chemical intermediate is largely obtained by acid-
catalyzed hydration of ethylene at high temperatures.
• Phenols occur widely throughout nature and also serve as intermediates in the industrial
synthesis of product as diverse as adhesives and antiseptics. Phenol itself is a general
disinfectant found in coal tar
NAMING:
• Alcohols are classified as Primary (1°), Secondary (2°), or tertiary (3°) depending on the
number of organic groups bonded to the hydroxyl-bearing carbon.
• The IUPAC system names simple alcohols as derivative of the parent alkene using the suffix -
ol
Rule 1
o Select the longest carbon chain containing the hydroxyl group, derive the parent name
by replacing the e- ending of the corresponding alkane with ol-
CH3-CH2-CH2-CH2-CH3 butane
CH3-CH2-CH2-CH2-OH butanol
Rule 2
o Number the alkane chain beginning at the end nearer the
hydroxyl group.
Rule 3
o Number the substituents according to their position in the chain, and write the name,
listing the substituents in alphabetical order and identifying the position to which the –
OH is bonded.
PREPARATION OF ALCOHOLS
Hydration of an alkane-The addition of water to an alkene occurs in living systems. Rather than use a
strong acid catalyst, which would destroy the system, reactions in cells use enzymes, biological
catalysts that work efficiently at the temperature and pH of the cell.
Oxidation of alcohol- Primary alcohols can be oxidized to form aldehydes and carboxylic acids;
secondary alcohols can be oxidized to give ketones. Tertiary alcohols, in contrast, cannot be
oxidized.
Oxidation of alcohols in living systems

• The oxidation of alcohols is an important reaction in living systems. Enzymes called
dehydrogenase catalyze these reactions. The major enzyme system(s) responsible for the
oxidation of ethanol, alcohol dehydrogenase.
GLYCEROL-It is widely distributed in all living tissue. It is obtained by the hydrolysis of animal fats or
plant oils, naturally occurring esters of glycerol and long-chain carboxylic acids. It is a colorless,
viscous liquid of sweet taste, b.p.290°, miscible in water.
PROPERTIES OF PHENOL
Carbonic acid, sometimes called, has antiseptic properties in dilute solution. All phenolic compounds
appear to have germicidal properties. Several commercial germicides contain phenols. Although
phenols are very toxic, dilute solutions of phenol are used as disinfectant.
Examples:
Draw the following molecules:
1) 1-propanol
2) 3-hexanol

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Module 3

ALKANES, ALKENES, ALKYNES

ALKANES: SATURATED HYDROCARBON

RULES IN NAMING ALKANES:

THE NAMING OF ALKENES AND ALKYNES

CHEMICAL REACTION OF ALKENES AND ALKYNES

HALOGENATION- addition of halogen atoms of alkenes and alkynes

GEOMETRIC ISOMERISM IN AROMATICS

meta (m-)= one carbon is between the substituents

para (p-)= two carbons between substituents

Oxidation of alcohols in living systems

Draw the following molecules:

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