ORGANIC CHEMISTRY

Dr Nam T. S. Phan
Faculty of Chemical Engineering
HCMC University of Technology
Office: room 211, B2 Building
Phone: 38647256 ext. 5681
Email: ptsnam@hcmut.edu.vn
1

CuuDuongThanCong.com https://fb.com/tailieudientucntt
 Chapter 7: ALKYNES
An sp
hybridized
carbon

CuuDuongThanCong.com https://fb.com/tailieudientucntt
 NOMENCLATURE OF ALKYNES
The IUPAC name of an alkyne is obtained by replacing
the “ane” ending of the corresponding alkane with “yne”

In common nomenclature, alkynes are named as

‘substituted acetylenes’

Both ethyne & acetylene are acceptable names for C2H2

3

CuuDuongThanCong.com https://fb.com/tailieudientucntt
 Lowest possible number, regardless of which
functional group gets the lower number

The same low number for both directions, lower number

4
for C=C
CuuDuongThanCong.com https://fb.com/tailieudientucntt
 PREPARATION OF ALKYNES
Sources of acetylene

CuuDuongThanCong.com https://fb.com/tailieudientucntt
Alkynes by elimination reactions

CuuDuongThanCong.com https://fb.com/tailieudientucntt
 REACTIONS OF ALKYNES
Acidic hydrogen

CuuDuongThanCong.com https://fb.com/tailieudientucntt
 Only for primary alkyl halides

CuuDuongThanCong.com https://fb.com/tailieudientucntt
Additions of hydrogen halides (AE)

CuuDuongThanCong.com https://fb.com/tailieudientucntt
 Additions of halogens (AE)

10

CuuDuongThanCong.com https://fb.com/tailieudientucntt
 Additions of water – hydration reactions

Markovnikov’s rule

Terminal alkynes are less reactive than internal alkynes,

need Hg2+ as a catalyst

11

CuuDuongThanCong.com https://fb.com/tailieudientucntt
Additions of boran – hydroboration & oxidation

12

CuuDuongThanCong.com https://fb.com/tailieudientucntt
 Regioselectivity

Markovnikov’s rule

Anti-Markovnikov 13

CuuDuongThanCong.com https://fb.com/tailieudientucntt
 Additions of hydrogen – hydrogenation

Product is
alkane

Product is
alkene

14

CuuDuongThanCong.com https://fb.com/tailieudientucntt
 Ozonolysis of alkynes

Ozonolysis used to be employed in structure

determination, but has been superseded by
spectroscopic methods
15

CuuDuongThanCong.com https://fb.com/tailieudientucntt
 Polymerizations

16

CuuDuongThanCong.com https://fb.com/tailieudientucntt