About The Authors

Chapter 7
These PowerPoint Lecture Slides were created and prepared by Professor
William Tam and his wife, Dr. Phillis Chang.

Alkenes and Alkynes I: Professor William Tam received his B.Sc. at the University of Hong Kong in
1990 and his Ph.D. at the University of Toronto (Canada) in 1995. He was an

Properties and Synthesis. NSERC postdoctoral fellow at the Imperial College (UK) and at Harvard
University (USA). He joined the Department of Chemistry at the University of
Guelph (Ontario, Canada) in 1998 and is currently a Full Professor and
Elimination Reactions Associate Chair in the department. Professor Tam has received several awards
in research and teaching, and according to Essential Science Indicators, he is
currently ranked as the Top 1% most cited Chemists worldwide. He has
of Alkyl Halides published four books and over 80 scientific papers in top international journals
such as J. Am. Chem. Soc., Angew. Chem., Org. Lett., and J. Org. Chem.

Dr. Phillis Chang received her B.Sc. at New York University (USA) in 1994, her
Created by M.Sc. and Ph.D. in 1997 and 2001 at the University of Guelph (Canada). She
lives in Guelph with her husband, William, and their son, Matthew.
Professor William Tam & Dr. Phillis Chang
Ch. 7 - 1 Ch. 7 - 2

1. Introduction
Alkynes
Hydrocarbons containing CC

Alkenes
Common name: acetylenes
Hydrocarbons containing C=C H
Old name: olefins N O I Cl
C
O C O
CH2OH Cl
F3C C Cl
Vitamin A C
H3C Cl
H3C

H H Efavirenz Haloprogin
Cholesterol (antiviral, AIDS therapeutic) (antifungal, antiseptic)
HO Ch. 7 - 3 Ch. 7 - 4

2. The (E) - (Z) System for Examples

Designating Alkene Diastereomers H
(2) vs

Cis-Trans System H
Useful for 1,2-disubstituted alkenes H H
Examples: trans -3-Hexene cis -3-Hexene
H Br
(1) Cl vs Cl
Br H Br
H H (3) Br Br vs
Br
trans -1-Bromo- cis -1-Bromo- trans -1,3- cis -1,3-
2-chloroethene 2-chloroethene Dibromopropene Dibromopropene
Ch. 7 - 5 Ch. 7 - 6

(E) - (Z) System
The Cahn-Ingold-Prelog (E) - (Z)
Difficulties encountered for Convention
trisubstituted and tetrasubstituted
alkenes The system is based on the atomic
number of the attached atom
CH3
e.g. Cl cis or trans? The higher the atomic number, the
Br
H higher the priority

Cl is cis to CH3
and trans to Br
Ch. 7 - 7 Ch. 7 - 8

The Cahn-Ingold-Prelog (E) - (Z) Examples

Convention CH3
(E) configuration the highest priority Cl 1
groups are on the opposite side of the 2 Br
double bond H
 E stands for entgegen; it means
opposite in German
(Z) configuration the highest priority On carbon 2: Priority of Br > C
groups are on the same side of the On carbon 1: Priority of Cl > H
double bond
highest priority groups
 Z stands for zusammer; it
are Br (on carbon 2)
means together in German
and Cl (on carbon 1)
Ch. 7 - 9 Ch. 7 - 10

Examples CH3 Other examples

Cl H (E )-1,2-Dichloroethene
Br
(1) Cl [or trans-1,2-Dichloroethene]
H 2
1 Cl
(E )-2-Bromo-1-chloropropene H C1: Cl > H
C2: Cl > H
Br
Cl Cl
2 (Z )-1-Bromo-1,2-dichloroethene
CH3 Cl
(2) 1
H Br C1: Br > Cl
(Z )-2-Bromo-1-chloropropene C2: Cl > H
Ch. 7 - 11 Ch. 7 - 12
 Other examples 3. Relative Stabilities of Alkenes
Br
Cis and trans alkenes do not have the
4
3 1 same stability
(3) 2
5
crowding
7
8 6
(Z )-3-Bromo-4-tert-butyl-3-octene
R R H R

C3: Br > C
C C C C
t n
C4: Bu > Bu H H R H

Less stable More stable

Ch. 7 - 13 Ch. 7 - 14

3A. Heat of Reaction

+ H2

Pt
C C + H H C C 7 kJ/mol
+ H2

H H H = -127 kJ/mol
Enthalpy

5 kJ/mol + H2

Heat of hydrogenation H = -120 kJ/mol

H -120 kJ/mol
H = -115 kJ/mol

Ch. 7 - 15 Ch. 7 - 16

3B. Overall Relative Stabilities of
Relative Stabilities of Alkenes

Alkenes

The greater the number of attached R R
>
R R
>
R H
>
R H
>
R R
>
R H
>
H H

alkyl groups (i.e., the more highly R R R H R H H R H H H H H H

tetra- tri- di- mono- un-
substituted the carbon atoms of the substituted substituted substituted substituted substituted

double bond), the greater the alkenes

stability.

Ch. 7 - 17 Ch. 7 - 18

Examples of stabilities of alkenes 4. Cycloalkenes

Cycloalkenes containing 5 carbon
(1) > atoms or fewer exist only in the cis
form

(2) > cyclopropene cyclobutene cyclopentene

Ch. 7 - 19 Ch. 7 - 20

Trans cyclohexene and trans
Trans cyclooctene has been isolated

cycloheptene have a very short lifetime and is chiral and exists as a pair of
and have not been isolated enantiomers

cyclohexene Hypothetical
trans - cyclohexene
(too strained to exist at r.t.) cis - cyclooctene trans - cyclooctenes

Ch. 7 - 21 Ch. 7 - 22

5. Synthesis of Alkenes via 6. Dehydrohalogenation of Alkyl

Elimination Reactions Halides

Dehydrohalogenation of Alkyl Halides
The best reaction conditions to use
H
H H H H when synthesizing an alkene by
base
C C
-HX
dehydrohalogenation are those that
H X
H
H H promote an E2 mechanism

Dehydration of Alcohols
H H
H H H+, heat H H E2
B: C C C C + B:H + X
C C
H OH -HOH H H X
H
Ch. 7 - 23 Ch. 7 - 24
6A. How to Favor an E2
E2 Mechanism

Use a secondary or tertiary alkyl halide
if possible. (Because steric hinderance
in the substrate will inhibit substitution)

When a synthesis must begin with a
primary alkyl halide, use a bulky base.
(Because the steric bulk of the base
will inhibit substitution)

Use a high concentration of a strong
and nonpolarizable base, such as an
alkoxide. (Because a weak and
polarizable base would not drive the
reaction toward a bimolecular reaction,
thereby allowing unimolecular
processes (such as SN1 or E1 reactions)
to compete.

Ch. 7 - 25 Ch. 7 - 26

Sodium ethoxide in ethanol 6B. Zaitsevs Rule

(EtONa/EtOH) and potassium tert-
Examples of dehydrohalogenations
butoxide in tertbutyl alcohol (t-BuOK/t- where only a single elimination product
BuOH) are bases typically used to is possible
promote E2 reactions EtONa
(1) (79%)
Br EtOH, 55oC

Use elevated temperature because
heat generally favors elimination over (2)
EtONa
(91%)
o
substitution. (Because elimination Br EtOH, 55 C
reactions are entropically favored over
t -BuOK
substitution reactions) (3) ( )
Br ( ) (85%)
Ch. 7 - 27
n t -BuOH, 40oC n
Ch. 7 - 28

H
When a small base is used (e.g. EtO

Rate = k H3C C CH3 EtO
or HO) the major product will be the
Br (2nd order overall) more highly substituted alkene (the
bimolecular more stable alkene)
Ha
Examples:
Ha Hb NaOEt
B Ha Hb (1)
EtOH
+

2-methyl-2-butene o
70 C
Br 69% 31%
(eliminate Ha) (eliminate Hb)
Br KOEt
Br (2) + +
b EtOH
H 51% 18% 31%
2-methyl-1-butene
Ch. 7 - 29 69% Ch. 7 - 30

Zaitsevs Rule Mechanism for an E2
E2 Reaction
In elimination reactions, the more Et O Et O
highly substituted alkene product CH3 CH3
H H H3C CH3
predominates C

C CH3
C C CH3 C C
H3C H3C H CH3

Stability of alkenes H Br H

Br +

Me Me Me Me Me H Et OH + Br
EtO removes Partial bonds in
C C > C C > C C
a proton; C=C is fully
the transition
Me Me Me H H Me CH breaks; formed and
state: CH and
new bond CBr bonds the other
Me Me Me H forms and Br products are
break, new
> C C > C C begins to CC bond forms EtOH and Br
H H H H depart
Ch. 7 - 31 Ch. 7 - 32

O Et 6C. Formation of the Less Substituted
H3C
CH3CH2 C C
H Alkene Using a Bulky Base
Et O H
Br
H CH3 H

Hofmanns Rule
C C CH3
H3 C
H

Br G1 Most elimination reactions follow
Free Energy

G2 Zaitsevs rule in which the most

CH3
CH3 CH3CH2 C CH2 + EtOH + Br
- stable alkenes are the major
EtO- + CH3CH2 C CH3 products. However, under some
Br
CH3 circumstances, the major
CH3CH C CH3 + EtOH + Br
-
elimination product is the less
substituted, less stable alkene
Reaction Coordinate
Ch. 7 - 33 Ch. 7 - 34

Case 1: using a bulky base Case 2: with a bulky group next

EtO CH3CH CHCH3 (80%) to the leaving halide
+
(small) CH3CH2CH CH2 (20%) less crowded -H
CH3CH2CHCH3
Me H Br H Me H
Br t CH3CH CHCH3 (30%) EtO
BuO
+ H3C C C C C H H3C C C C CH2
(bulky) CH3CH2CH CH2 (70%)

Me H Me H Me H Me
EtO
(small base) (mainly)
H H H H tBuO more crowded -H
H C C C C H (bulky base)
H H Br H Ch. 7 - 35 Ch. 7 - 36

Zaitsev Rule vs. Hofmann Rule Examples

Examples
Hb Br
a b Ha
H H (2) +
(1) +
(eliminate Ha) (eliminate Hb)
Br a b
(eliminate H ) (eliminate H )
NaOEt, EtOH, 70oC 91% 9%
o
NaOEt, EtOH, 70 C 69% 31% t t o
KO Bu, BuOH, 75 C 7% 93%
t t o
KO Bu, BuOH, 75 C 28% 72%

Ch. 7 - 37 Ch. 7 - 38

6D. The Stereochemistry of E2

E2
Reactions

The 5 atoms involved in the transition B B
H H LG
state of an E2 reaction (including the
C C C C
base) must lie in the same plane
LG

The anti coplanar conformation is the
preferred transition state geometry Anti coplanar Syn coplanar
transition state transition state
The anti coplanar transition state is (preferred) (only with certain
staggered (and therefore of lower rigid molecules)
energy), while the syn coplanar
transition state is eclipsed
Ch. 7 - 39 Ch. 7 - 40

Orientation Requirement
E2 Elimination where there are two

H and Br have to be anti periplanar axial hydrogens
(trans-coplanar) (a) 1
EtO H3C 4 CH(CH3)2
Examples a
EtO b H 3 2
H 1-Menthene (78%)
CH3CH2 + EtO CH3CH2 1 CH(CH3)2
H3C (more stablealkene)
4 H
3
2
Br CH3 CH3 H
H Cl
1
since: Br H3C 4 CH(CH3)2
(b)
CH3CH2 Only H is Both Ha
and hydrogensHb 3 2
H 2-Menthene (22%)
H anti periplanar are anti to the chlorine in
H CH3 this, the more stable (less stable alkene)
to Br
EtO conformation
Ch. 7 - 41 Ch. 7 - 42

E2 elimination where the only axial The transition state for
hydrogen is from a less stable the E2 elimination is
Conformer anti coplanar
H CH3
H Cl CH3 CH3
1 CH(CH3)2 Cl Cl
H3C 4 2 H H
3 Cl
H H H H
H H
H H H CH(CH3)2 H H
H CH(CH3)2 H CH(CH3)2
Menthyl chloride Menthyl chloride
(more stable conformer) (less stable conformer) OEt
Elimination is not possible Elimination is possible for
for this conformation this conformation because
because no hydrogen is anti the green hydrogen is anti
to the leaving group to the chlorine H3C CH(CH3)2
2-Menthene (100%)
Ch. 7 - 43 Ch. 7 - 44

7. Acid-Catalyzed Dehydration of
The temperature and concentration of

Alcohols acid required to dehydrate an alcohol
depend on the structure of the alcohol

Most alcohols undergo dehydration substrate
(lose a molecule of water) to form an Primary alcohols are the most difficult to
alkene when heated with a strong acid dehydrate. Dehydration of ethanol, for
example, requires concentrated sulfuric
acid and a temperature of 180C
HA H H H H
C C C C + H2O conc. H2SO4
heat H C C H C C + H2O
H OH
180oC H H
H OH
Ethanol (a 1o alcohol)
Ch. 7 - 45 Ch. 7 - 46

Secondary alcohols usually dehydrate Tertiary alcohols are usually so easily

under milder conditions. Cyclohexanol, dehydrated that extremely mild
for example, dehydrates in 85% conditions can be used. tert-Butyl
phosphoric acid at 165170C alcohol, for example, dehydrates in 20%
aqueous sulfuric acid at a temperature
OH of 85C
85% H3PO4
+ H2O
165-170oC CH3 CH2
20% H2SO4
H3C C OH + H2O
Cyclohexanol Cyclohexene CH3 85oC H3C CH3
(80%)
tert-Butyl alcohol 2-Methylpropene
(84%)
Ch. 7 - 47 Ch. 7 - 48
 The relative ease with which
Some primary and secondary alcohols
alcohols will undergo dehydration is also undergo rearrangements of their
in the following order: carbon skeletons during dehydration
CH3

R R H H3C C CH CH3
CH3 OH 85% H3PO4
R C OH > R C OH > R C OH
3,3-Dimethyl-2-butanol 80oC
R H H
H3C CH3 H3C CH3
3o alcohol 2o alcohol 1o alcohol
C C + C CHCH3
H3C CH3 H2C
2,3-Dimethyl-2-butene 2,3-Dimethyl-1-butene
Ch. 7 - 49 (80%) (20%) Ch. 7 - 50

Notice that the carbon skeleton of 7A. Mechanism for Dehydration of 2o

o
the reactant is & 3 Alcohols: An E1
E1 Reaction
C

Consider the dehydration of tert-butyl
C C C C
alcohol + H O
C Step 1 H
while that of the product is CH3 H H3C H
C C
H3C C O H + H O H3C C O H
C C
CH3 H CH3
C C
protonated
alcohol
Ch. 7 - 51 Ch. 7 - 52

Step 2 7B. Carbocation Stability & the

H3C H CH3
Transition State
H3C C O H C + H O
Recall
H3C CH3
CH3 H
a carbocation R H H H
R C > R C > H C > H C
Step 3
R R R H
H
H
CH2 3o > 2o > 1o > methyl
H C H + H O C + H O
most least
C H3C CH3
H3C CH3 H H stable stable
2-Methylpropene
Ch. 7 - 53 Ch. 7 - 54
 7C. A Mechanism for Dehydration of
Primary Alcohols: An E2
E2 Reaction
protonated
o
1 alcohol alcohol
H H H
fast
C C O H + H A C C O H
H H acid H H
slow
catalyst
r.d.s
+A
H H
conjugate
H O + HA + C C
base
H alkene
Ch. 7 - 55 Ch. 7 - 56

8. Carbocation Stability & Occurrence
Step 1

of Molecular Rearrangements
CH3 CH3
8A. Rearrangements during H3C C CH3
CH H3C C CH CH3
Dehydration of Secondary Alcohols
CH3 CH3 O H CH3 OH2
H3C C CH CH3 H protonated
CH3 OH 85% H3PO4 alcohol
heat + H O H
3,3-Dimethyl-2-butanol

H3C CH3 H3C CH3 + H O

C C + C CHCH3 H
H3C CH3 H2C
2,3-Dimethyl-2-butenol 2,3-Dimethyl-1-butene
(major product) (minor product)
Ch. 7 - 57 Ch. 7 - 58

Step 2
Step 3
CH3 CH3
CH3 CH3 + +
H3C C CH CH3 H3C C CH CH3
H3C C CH CH3 H3C C CH CH3
CH3 CH3
H3C OH2 CH3
o transition state
a 2o carbocation 2 carbocation
(less stable)
3o carbocation
+ H O
o
(more stable)
H The less stable 2 CH3
carbocation rearranges
o H3C C CH CH3
to a more stable 3
carbocation. CH3
Ch. 7 - 59 Ch. 7 - 60

Step 4 (a)
Other common examples of
A carbocation rearrangements
(b) H

(a) or (b) H CH2 C C CH3 Migration of an allyl group

CH3 CH3
(a) (b) CH3 CH3
methanide
(major) (minor) H3C C CH CH3 H3C C C CH3
migration
H CH3 CH3
H3C CH3 H2C
HA + C C C C CH3 + HA a 2o carbocation 3o carbocation
H3C CH3 H3C CH3
less stable alkene more stable alkene
Ch. 7 - 61 Ch. 7 - 62

8B. Rearrangement after Dehydration

of a Primary Alcohol
Migration of a hydride R
R H H C H
H
C C C O H +H A C C + H O +H A
H H E2
hydride H R H R H H
H3C C CH CH3 H3C C C CH3 R R
migration
C H C H
CH3 CH3 H H
C C +H A C C H + A
a 2o carbocation 3o carbocation R H protonation
R H
R R
C H C H
+ H
A C C H C C H +H A
R deprotonation R
H H
Ch. 7 - 63 Ch. 7 - 64

9. The Acidity of Terminal Alkynes
Comparison of acidity and basicity of

Acetylenic hydrogen 1st row elements of the Periodic Table
Relative acidity
sp sp2 sp3
H H H OH > H OR > H C CR > H NH2 > H CH CH2 > H CH2CH3
H H
H C C H C C H C C H pKa 15.7 16-17 25 38 44 50
H H H H
pKa = 25 pKa = 44 pKa = 50 Relative basicity

Relative basicity of the conjugate base OH < OR < C CR < NH2 < CH CH2 < CH2CH3

CH3CH2 > CH2 CH > CH CH

Ch. 7 - 65 Ch. 7 - 66
10. Synthesis of Alkynes by
Mechanism
Elimination Reactions
H
H H

Synthesis of Alkynes by NH2
R
R C C R R
Dehydrohalogenation of Vicinal E2
Dihalides Br Br Br

H H NH2
NaNH2
C C C C
heat R R
Br Br

Ch. 7 - 67 Ch. 7 - 68

Examples
Synthesis of Alkynes by

Br Dehydrohalogenation of Geminal
H NaNH2
(1)
Dihalides
heat O Cl Cl
H Br (78%)
PCl5

R CH3 0oC R CH3

Br H
Ph Br2 Ph gem-dichloride
(2)
Ph CCl4 Ph NaNH2
H Br 1. NaNH2 (3 equiv.), heat
heat
2. HA

Ph Ph
Ph H
Ch. 7 - 69 Ch. 7 - 70

11. Replacement of the Acetylenic
Acetylide anions are useful

Hydrogen Atom of Terminal intermediates for the synthesis of other
Alkynes alkynes

The acetylide anion can be prepared by R R' + X

R R' X
NaNH2
R H R Na + NH3
liq. NH3
2nd step is an SN2 reaction, usually
only good for 1o R
o o

2 and 3 R usually undergo E2
elimination
Ch. 7 - 71 Ch. 7 - 72
 Ph H

Examples 13. Hydrogenation of Alkenes
NaNH2
liq. NH3 H2
H H
I Pt, Pd or Ni
Ph Na C C C C
solvent
CH3 I heat and pressure
H

SN2 E2 H2
H H
Pt, Pd or Ni
C C C C
Ph CH3 Ph H solvent
heat and pressure H H
+ +
NaI

Hydrogenation is an example of
+
addition reaction
I Ch. 7 - 73 Ch. 7 - 74

Examples 14. Hydrogenation: The Function

H
of the Catalyst
H2
H
Rh(PPh3)3Cl
Hydrogenation of an alkene is an
exothermic reaction
H -120 kJ/mol
H hydrogenation
H2 R CH CH R R CH2 CH2 R
Pd/C + H2 + heat
H

Ch. 7 - 75 Ch. 7 - 76

14
14A.
A. Syn and Anti Additions

An addition that places the parts of the
reagent on the same side (or face) of
the reactant is called syn addition
syn
C C + X Y C C
addition
X Y

Pt
C C + H H C C
H H

Catalytic hydrogenation is a syn addition.

Ch. 7 - 77 Ch. 7 - 78
 15. Hydrogenation of Alkynes

An anti addition places parts of the H2 H H
adding reagent on opposite faces of Pt or Pd
the reactant H2

Y H H
anti
C C + X Y C C
addition
X
H H

Using the reaction conditions, alkynes
are usually converted to alkanes and
are difficult to stop at the alkene stage
Ch. 7 - 79 Ch. 7 - 80

15
15A.
A. Syn Addition of Hydrogen:
Semi-hydrogenation of alkynes using
Synthesis of cis-Alkenes Ni2B (P-2) or Lindlars catalyst causes

Semi-hydrogenation of alkynes to syn addition of hydrogen
alkenes can be achieved using either Examples
the Ni2B (P-2) catalyst or the Lindlars H2 H H
catalyst (97%)
Ni2B (P-2)
Nickel boride compound (P-2 catalyst) (cis)
 O NaBH4
Ni
EtOH
Ni2B H2 H H
O CH3
2 (P-2) Ph CH3 (86%)
Pd/CaCO3 Ph CH3
Lindlars catalyst quinoline
 Pd/CaCO3, quinoline Ch. 7 - 81 Ch. 7 - 82

15
15B.
B. Anti Addition of Hydrogen:
Synthesis of trans-Alkenes

Example

Alkynes can be converted to trans-
alkenes by dissolving metal reduction

Anti addition of dihydrogen to the 1. Li, liq. EtNH2, -78oC
alkyne 2. NH4Cl
H
1. Li, liq. NH3, -78oC R'
H
R R' R
2. aqueous work up
H
H
anti addition
Ch. 7 - 83 Ch. 7 - 84

Mechanism 16. An Introduction to Organic Synthesis
radical anion vinyl radical
16
16A.
A. Why Do Organic Synthesis?
R R H
H NHEt
R C C R C C C C
To make naturally occurring compounds
R R which are biologically active but difficult (or
Li impossible) to obtain
Li
AcO O OH
Ph O
R H EtHN H R H
BzN
C C C C Anti-tumor,
H OH O
H R R HO
H anti-cancer
OAc
TAXOL OH
agent
trans alkene vinyl anion
Ch. 7 - 85 Ch. 7 - 86

TAXOL TAXOL

Isolated from Pacific Yew tree
Approved by the U.S. Food & Drug
Leaves Administration in 1992 for treatment of
several types of cancer, including breast
Cones and Fruit
cancer, lung cancer, and melanoma

An estimation: a 100-year old yew tree
must be sacrificed in order to obtain 300 mg
of Taxol, just enough for one single dose for
a cancer patient

Obviously, synthetic organic chemistry
seed pollen cones methods that would lead to the synthesis of
usually appear on separate Taxol would be extremely useful
male and female trees Ch. 7 - 87 Ch. 7 - 88

16
16B.
B. Retrosynthetic Analysis
When doing retrosynthetic analysis, it is
necessary to generate as many possible
precursors, hence different synthetic routes,
target 1st 2nd starting as possible
molecule precursor precursor compound 2nd precursor a
1st precursor A
2nd precursor b

2nd precursor c
target
1st precursor B
molecule
2nd precursor d

2nd precursor e
1st precursor C
2nd precursor f
Ch. 7 - 89 Ch. 7 - 90
16
16C.
C. Identifying Precursors
Retrosynthetic Analysis
SN2 on 1o alkyl halide: good

Synthesis of
X
C C +
disconnection 1 +

C C
C C

(target molecule) disconnection 2

+ X +

SN2 on 2o alkyl halide: poor

will get E2 as major pathway
Ch. 7 - 91 Ch. 7 - 92

Synthesis 16
16D.
D. Raison dEtre
Summary of Methods for the Preparation of
NaNH2
Alkenes
C C H C C Na (Dehydrohalogenation
liq. NH3 of alkyl halides)
C C C C
H X base, heat H+ H OH
(SN2) I
heat (Dehydration
of alcohols)
H2, Ni2B (P-2) C C
NaI + C C or Lindlar's catalyst Li, liq. NH3
(give (Z)-alkenes) (give (E)-alkenes)

C C (Semi- (Dissolving C C
hydrogenation metal reduction
Ch. 7 - 93 of alkynes) of alkynes) Ch. 7 - 94

Summary of Methods for the Preparation of

Alkynes
X (Dehydrohalogenation Cl
H R' Cl R'
of geminal dihalide)
R H R H
X NaNH2 NaNH2 H
heat
R C C R'
heat
 END OF CHAPTER 7 
(Dehydrohalogenation
of vicinal dihalide)

(Deprotonation of terminal 1. NaNH2, liq. NH3

alkynes and SN2 reaction of
2. R'-X (R' = 1o alkyl group)
the acetylide anion)

R C C H
Ch. 7 - 95 Ch. 7 - 96