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Chapter 4

The document discusses the nomenclature, synthesis, and reactivity of alkanes. It describes various methods for synthesizing alkanes, including hydrogenation of alkenes and alkynes, reduction of carbonyl compounds, and reactions of alkyl halides. It also covers the radical halogenation of alkanes, noting that bromination is more selective than chlorination. Stereochemistry is maintained in the halogenation of sp2 hybridized carbon atoms.

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22 views24 pages

Chapter 4

The document discusses the nomenclature, synthesis, and reactivity of alkanes. It describes various methods for synthesizing alkanes, including hydrogenation of alkenes and alkynes, reduction of carbonyl compounds, and reactions of alkyl halides. It also covers the radical halogenation of alkanes, noting that bromination is more selective than chlorination. Stereochemistry is maintained in the halogenation of sp2 hybridized carbon atoms.

Uploaded by

Quỳnh Anh Trần
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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ALKANES

sp3 carbon

1
NOMENCLATURE OF ALKANES

2
NOMENCLATURE OF ALKYL GROUPS

3
NOMENCLATURE OF SUBSTITUTED
ALKANES

Principal chain: longest continuous carbon


chain in the molecule.
4
OCCURRENCE OF ALKANES

5
SYNTHESIS OF ALKANES

From hydrogenation of alkenes

6
SYNTHESIS OF ALKANES

From hydrogenation of alkynes

7
SYNTHESIS OF ALKANES
From reduction of carbonyl compounds

Wolff-Kishner reduction

Clemmensen reduction 8
REDUCTION OF “C=O” TO “CH2”
Clemmensen vs. Wolff-Kishner reductions

group prone to acid


9
SYNTHESIS OF ALKANES FROM ALKYL HALIDES

Wurtz synthesis

Mechanism
SN2

10
SYNTHESIS OF ALKANES FROM ALKYL HALIDES

Reactivity: primary > secondary, tertiary alkyl halides


are UNREACTIVE

minor major

Only useful for synthesis of symmetrical alkanes

11
SYNTHESIS OF ALKANES FROM ALKYL HALIDES

Corey-House synthesis: stepwise synthesis of new


alkanes -> practical method for joining two alkyl groups

Example

Tertiary are fine


NO TERTIARY!

12
SYNTHESIS OF ALKANES FROM ALKYL HALIDES
Another example

And another one


NO CH3I!

sp2 carbons are fine 13


REACTIVITIES OF ALKANES

• Alkanes have only strong s bonds


• Electronegativity of C & H are approximately
the same
• None of the atoms in alkanes have any
significant charge
• Neither nucleophiles nor electrophiles are
attracted

Alkanes are very unreactive 14


RADICAL HALOGENATION

15
RADICAL HALOGENATION

Rate: Fluorination > Chlorination > Bromination >


Iodination.
Chlorination and bromination are important.
16
RADICAL HALOGENATION

Chlorination is much less selective than bromination


17
RADICAL HALOGENATION

More reactive means less selective! 18


RADICAL HALOGENATION

19
RADICAL HALOGENATION

Bromination is much more


selective than chlorination 20
RADICAL HALOGENATION

21
RADICAL HALOGENATION

NOTE: Addition will occur at low temp. and in the dark. 22


STEREOCHEMISTRY OF RADICAL
HALOGENATION

sp2 hybridized 23
STEREOCHEMISTRY OF RADICAL
HALOGENATION

24

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