Preparations of Alkanes,Alkenes,Alkynes

PREPARATION OF ALKANES,ALKENES,ALKYNES Presented by K.BINDU MEENAKSHI

REGD NO:11AB1R0028

Under the Guidance of

MR.A.VISWANATH M.Pharm Associate Professor Department Of Organic Chemistry

VIGNAN PHARMACY COLLEGE

(Approved by AICTE, AICTE, PCI & affiliated to JNTU-K) VADLAMUDI, GUNTUR DISTRICT DI STRICT  –  ANDHRA  ANDHRA PRADESH, INDIA

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CONTENTS:

INTODUCTION  NOMENCLATURE  NOMENCLA TURE METHOD MET HOD OF PREP PREPARA ARATIO TION N PHYSICAL PHYSICA L PROPERTIES PROPERTIES CHEMICAL CHEMIC AL PROPERTIES PROPERTIES

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STRUCTURE STRUCT URE OF OF ALKANES ALKANES:: Alkanes

contains only a single bond.

General formula for alkanes is CnH2n+2.

•

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All the carbon atoms are sp3 hybridized. C-C Bond length is 1.54A˚(or)0.154nm and the C-H Bond length is 1.10A˚(or)0.110nm.

The bond angle is109.28˚.

Sp3-Sp3

1.10A˚

109.28˚

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NOMENCLA NOMENCL ATURE OF ALKANES:

Suffix:-ane

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CH3 CH3

CH

CH3

METHYLPROPANE

CH3 1

2

3

4

5

CH3   CH CH CH2 CH2 CH3 2-METHYLPENTANE

CH3 1

2

3

4

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METHODS OF PREP METHODS PREPARA ARATION TIONS S OF ALKANES: HYDROGENA YDROGENATION TION OF ALKENES OR ALKYNES: a)

R-CH=CH2 + H2 ALKENE

Ni

∆

R-CH2-CH3

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EDUCTION OF ALKYL HALIDE: R EDUCTION

Alkyl halides undergoes reduction with nascent hydrogen to form alkanes.

R-X + 2[H] ALKYLHALIDE

R-H + HX ALKANE

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HYDROL YDROLYSIS YSIS OF GRIGNARD REAGENT RE AGENT: Alkyl halide on treatment with magnesium magnesium in anhydrous ether gives Grignard reagent. RX + Mg

ETHER

RMgX

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WURTZ SYNTHESIS: Higher alkanes are produced by heating an alkyl halide with sodium metal in dry ether solution. R-X + 2Na + X-R

ETHER 

R-R + 2NaX

SYMETRICAL ALKANE

CH -Br + 2Na + Br-CH

ETHER 

CH -CH  + 2NaBr

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COREY HOUSE ALKANE ALKANE SYNTHESIS: Developed by E.J.Corey and Herbert House in 1960s. Lithium dialkyl copper and an alkyl halide on reaction gives alkanes.

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KOLBE’S SYNTHESIS:

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PHYSICIAL PHYSICIA L PROPERTIES PROPERTIES OF ALKANES ALKANES::

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IR Spectrum :

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CHEMICAL PROPERTIES OF ALKANES:

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BY DEHYDROHALOGENATION OF ALKYL HALIDE: When an alkyl halide is heated with an alcoholic solution of sodium or potassium hydroxide , a molecule of hydrogen halide is eliminated and an alkene is formed.

R

CH

CH2 + KOH

ALCOHOL ∆

H

X

R

CH ALKENE

CH2 + KX + H2O

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BY DEHALOGENATION OF VICINAL DIHALIDE: Alkenes are formed when vic-dihalide are heated with zinc dust in ethyl alcohol. R

CH3 CH 3 Br 

CH2 + Zn

ALCOHOL

R ∆

Br 

VIC-DIHALIDE ALCOHOL

CH ALKENE

CH2  + ZnBr 2

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BY CONTROLLED HYDRGENATION OF ALKYNES: Alkynes react with lindlar’ lindlar ’s catalyst to give alkenes.

R C C H + H2 ALKYNE

CH3 C C H + H2

Pd-CaCO3 QUINOLINE

R CH

CH2

ALKENE

Pd-CaCO3 QUINOLINE

CH CH2 CH3   CH

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BY CRACKING OF ALKANES : Alkanes when heated at 500-800˚c in the absence of air decompose to yield lower molecular weight alkenes,alkanes,hydrogen. CH3-CH3 ETHANE

CH3-CH2-CH3 PROPANE

CH2=CH2 + CH4 + H2 ETHYLENE

CH3-CH=CH2 + CH2=CH2 PROPENE

ETHYLENE

+ CH + H

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PHYSICAL PROPERTIES:  All are colorless and odorless except ethene. Insoluble Less

in water and quiet soluble in non polar solvents.

dense than water.

Boiling

point increases with carbon number.

Melting

point , boiling point, specific

gravity rises with increase of molecular weight in homologous series.

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CHEMICAL PROPERTIES: Alkenes are more reactive than alkanes because of π electrons of the double bond. ADDITION OF HYDROGEN HALIDES:

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MECHANISM: STEP 1:

CH3 CH2 CH2 +  Br  1˚CARBOCATION

CH CH2 + H Br  CH3   CH PROPENE

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MECHANISM OF ADDITION OF HYDROGEN HALIDE: STEP 1: H

H

CH3

C

C

CH3 + H

Br 

H

H

CH3   C

C

C H3 + Br 

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ADDITION OF HYPOHALOUS ACID: Alkenes react with hypohalous acid to give halohydrins. CH2

CH2   + HO Cl

ETHYLENE

OH

Cl

CH2

CH2

ETHYLENE CHLOROHYDR CHLOROHYDRIN IN

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ADDITION OF WATER: Alkenes react with water in the presence of a strong acidic catalyst OH

to form alcohol. H

⁺

CH3-CH=CH2 + H2O PROPENE

l

CH3-CH-CH3 2-PROPANOL

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ADDITION OF H2SO4:

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OXIDATION OXIDA TION WITH COLD KMnO 4 SOLUTION:

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ADDITION OF HALOGEN: Alkenes react rapidly with halogens in carbon tetrachloride solvent to

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OXYMERCURATION-D OXYMERCURA TION-DEMERCURA EMERCURATION TION OF

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MECHANISM:

OAc H 2O

H

H

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OXIDATION OXIDA TION WITH WI TH KMnO 4: Oxidation of alkynes with alkaline KMnO4 forms carboxylic acid and CO2.

CH3

C

C

H + 4

PROPYNE

CH3

COOH + CO2

ACETIC ACID

POLYMERIZATION: Alkynes when passed through a red hot tube gives aromatic

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OZONOLYSIS: Alkynes react with ozone to give ozonide gives following product. O R

C

C

ALKYNE

R + O3 

R

C

C

O

O

OZONIDE

H2O

R



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MERCURIC ION-CATALYSED HYDRATION: Alkynes undergo acid-catalyzed addition of water , in the  presence of mercuric ion as a catalyst. OH CH3 C

C

H + H 2O

PROPYNE

MECHANISM: STEP 1:

H2SO4 HgSO4

CH3

C ENOL

O CH2

H⁺

CH3

C

CH3

ACETONE

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STEP 2: Hg2+ CH3

C

H3C

C

H

C

C H

+O

O H

Hg+

H

H

H

STEP 3:

H3C

H H

O

Hg+ C

+ +O

H3C

C

Hg+ C

H

O

+ H3O+

C H

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STEP 4:

o

Hg+

H3C C

CH3

C

HO

H

STEP 5:

H + CH3

C

CH3 C CH2 Hg+ + H2O

CH2 Hg+

OXONIUM ION

H STEP 6:

H +

Hg+

H + O

O + O

CH2

KETO FORM

ENOL FORM

H

C

H

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CONCLUSION: Alkane , Alkenes , alkynes are

the basic fundamental structure in

organic chemistry. Almost

all the compounds contains single or double or triple bonds

in their structure.

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REFERENCES: Arun

Bahl,B.S Bahl,B.S Bahl , Advanced Organic Chemistry ,

Pg No:184-240,262-356.

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

Vogel's, ogel's , Practical Practi cal Organic Organi c Chemistry Chemistr y, 5th edition, Pg No:470-517.

Lloyd

N . Ferguson , Textbook of Organic

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ACKNOWLEDGEMENT I would like to thank my guide MR.A.VISWANATH sir for his constant support and guidance.

I also thank our principal Dr . P.SRINIVAS BABU sir and

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