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Chapter 4

This document summarizes key information about alkynes from their structure and nomenclature to methods of preparation and common reactions. Alkynes contain a carbon-carbon triple bond and can be internal or terminal. They are prepared by dehydrohalogenation of alkyl dihalides or alkylation of terminal alkynes. Alkynes undergo addition reactions with hydrogen, halogens, hydrogen halides, and water. Common reactions include hydrogenation to alkenes and alkane, halogenation, hydrohalogenation, and hydration to ketones. Important alkynes such as acetylene are used for welding, plastic production, and portable lighting.

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15 views32 pages

Chapter 4

This document summarizes key information about alkynes from their structure and nomenclature to methods of preparation and common reactions. Alkynes contain a carbon-carbon triple bond and can be internal or terminal. They are prepared by dehydrohalogenation of alkyl dihalides or alkylation of terminal alkynes. Alkynes undergo addition reactions with hydrogen, halogens, hydrogen halides, and water. Common reactions include hydrogenation to alkenes and alkane, halogenation, hydrohalogenation, and hydration to ketones. Important alkynes such as acetylene are used for welding, plastic production, and portable lighting.

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2022680144
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© © All Rights Reserved
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CHAPTER 4

ALKYNES
OUTLINES
1.0 Introduction

1.1 Structure and Nomenclature


✓ IUPAC and common names

1.2 Method of Preparation:


✓ Dehydrohalogenation of alkyl dihalides
✓ Alkylation of salt of terminal alkynes

1.3 Reactions of alkynes:


✓ Hydrogenation
✓ Halogenation
✓ Hydrohalogenation
✓ Hydration (H2O, H2SO4, HgSO4).

1.4 Uses of alkynes


1.0 INTRODUCTION
✓ Alkynes are hydrocarbon that have at least one triple
bond C≡C.
✓ General formula : CnH2n-2.
✓ Disubstituted alkynes, R-C≡C-R’, are described as
internal alkynes
✓ Monosubstituted alkynes, R-C≡C-H, are described as
terminal alkynes
1.1 NOMENCLATURE

Parent chain
Numbering
→Longest Locate and Arrange
carbon chain → C≡C must at name →Alphabetical
lowest carbon substituents
→ Must order
number
include C≡C
Basic
Alkynes

Alkynols Alkenynes
BASIC ALKYNES
ALKENYNES
(double bond + a triple bond)
ALKYNOLS
(Triple bond + an alcohol)
PREPARATION OF
ALKYNES

DEHYDROHALOGENATION
OF ALKYL DIHALIDES ALKYLATION OF SALT OF
TERMINAL ALKYNES
(-HX)
DEHYDROHALOGENATION OF
ALKYL DIHALIDES
Elimination of hydrogen and halogen (-HX) from an alkyl dihalide to form alkyne.

✓ Vicinal or geminal dihalides may produce internal or terminal alkynes


i) Preparation of internal alkynes
➢ Condition: In extremely basic conditions such as fused (molten) KOH or
alcoholic KOH in sealed tube and heated to temperatures close to 200°C.

ii) Preparation of terminal alkynes


➢ Condition: In strong base i.e. NaNH2 (sodium amide) at lower temperature
(150°C), followed by adding water.
EXAMPLE
Alkylation of salt of terminal
alkynes
Addition of alkyl group (R-group) to the terminal alkyne

➢ Terminal acetylenes can be deprotonated by a very strong base, such as sodium


amide.
✓ Reason: the terminal alkyne C-H bond is not strongly acidic.

➢ Internal alkynes do not react with the base because do not have acetylenic
protons.
EXAMPLE
MECHANISM
R C C H NaNH2 R C C Na NH3
terminal alkynes sodium amide sodium acetylide

SN 2
R C C Na R' X R C C R' NaX
(R'-X must be a primary alkyl halide)

or

1) NaNH2
R C C H R C C R'
2) R'-X
EXAMPLE
1.3 REACTION OF ALKYNES

ADDITION REACTION
I) HYDROGENATION
ALKYLATION OF SALT OF
II) HALOGENATION
TERMINAL ALKYNES
III) HYDROHALOGENATION
IV) HYDRATION
ADDITION REACTIONS
✓ Alkynes undergo addition reactions because they contain weak π bonds.

✓ Two sequential reactions take place;


i. First addition of one equivalent of reagent forms an alkene,
ii. Next, second addition of reagent will yield an alkane with four new bonds.

✓ Alkynes are electron rich & react with electrophiles.


HYDROGENATION
Addition of hydrogen, H2 ( 1 or 2 mole) to the triple bond
H H
Pt, Pd or Ni
R C C R' 2H2 R C C R'

H H
EXAMPLES
H H
Pt, Pd or Ni
H C C CH2CH3 2H2 H C C CH2CH3
1-butyne H H
butane

H H
Pt, Pd or Ni
CH3 C C CH2CH3 2H2 CH3 C C CH2CH3
2-pentyne H H
pentane
CATALYTIC HYDROGENATION TO
CIS AND TRANS ALKENES
i) Alkynes to cis-alkene
Lindlar's catalyst R R'
R C C R' + H2 C C
or Ni2B (Nickel boride) H H
alkynes
cis-alkene

Lindlar's catalyst = a poisoned palladium catalyst, composed of powdered barium sulfate ii) Alkynes to trans-alkene
coated with palladium, poisoned with quinoline
= Pd/BaSO4, quinoline
EXAMPLE
HALOGENATION
Addition of halogen to the triple bond

✓ Addition of 1 mole X2, product = dihaloalkene.


✓ Addition of 2 moles X2, product = tetrahalide alkane.
EXAMPLE
HYDROHALOGENATION
Addition of hydrogen halide (HX) to the triple bond.

✓ Addition of 1 mole HX, product = vinyl halide (have “=”).


✓ Addition of 2 moles X2, product = geminal dihalide.

Follow Markovnikov’s orientation.


EXAMPLE
Addition of one mole of HX

✓ Addition of two moles HX


HYDROHALOGENATION
Addition of hydrogen bromide (HBr) with peroxide, ROOR or H2O2

Follow anti-Markovnikov orientation.


HYDRATION
Addition of water (H2O) with the presence of H2SO4, HgSO4

✓ Initial addition product, an enol, is unstable &


✓ Rearranges to a product containing a carbonyl group, C=O that
is ketone.

Follow Markovnikov’s orientation.


EXAMPLE
EXAMPLE
USES
ACETYLENE

- WELDING TORCH
- USED PRODUCTION OF POLYETHYLENE PLASTIC
- PORTABLE LIGHTING
THE END

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