4

C .
C + C : -

An Introduction to
Organic Reactions

CHAPTER SUMMARY

In the previous three chapters we have progressed from atoms and electrons to
bonds and molecules to sophisticated structural representations and
nomenclature of organic molecules. Chapter 4 uses this knowledge of organic
structure to introduce organic chemical reactions.

4.1 General Principles of Organic Reactions

A. Types of Reactions: The Reaction Equation
A reaction equation describes what happens in a chemical reaction by
displaying the reactants and products. It describes what bonds break in the
reactants and what new bonds form in the products. There are three main
types of organic reactions. In substitution reactions, an atom or group of
atoms is replaced by another species. Elimination reactions involve the
removal of a pair of atoms or groups from two adjacent atoms to form a

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multiple bond. In addition reactions atoms or groups add to adjacent atoms

involved in a multiple bond; the multiple bond is reduced.
B. Reaction Mechanisms
A reaction mechanism is a step-by-step description of how a reaction
occurs. The reaction equation describes what happens; the mechanism
describes how the reaction happens.
C. Reaction Mechanisms and Potential Energy Diagrams
Potential energy diagrams are used to depict energy changes during
chemical reactions. The vertical axis of the diagram is potential energy and
the horizontal axis describes reaction progress. Energy is required to break
bonds and potential energy increases as bonds break in during the initial
stages of a reaction. As new bonds form and a reaction comes to a
conclusion, energy is released. The difference in energy between the
starting materials and the products is called the heat of reaction. If the
products are of lower energy than the reactants (more energy is released in
bond formation than consumed in bond breaking), heat is evolved and the
reaction is exothermic. The opposite is an endothermic reaction.
The process of bond cleavage or bond formation is called a transition
state and appears as a maximum in the potential energy diagram curve. An
intermediate is a short lived species formed in a multi-step reaction
mechanism and is the result of a transition; it appears as a minimum on the
reaction progress curve. The rate of a reaction depends on the difference in
energy between that of the starting materials and an intermediate (or the
products in a one step reaction); this is the energy of activation.
D. Reaction Intermediates
Multistep reaction mechanisms proceed through reaction intermediates.
There are three major reaction intermediates involving carbon. A
carbocation has a carbon with only three bonds, six outer-shell electrons
and a positive charge. A free radical is a neutral carbon with only three
bonds and seven outer shell electrons, one of which is unpaired. A
carbanion has only three bonds but has eight outer shell electrons, one of
which is a non-bonding pair, and a negative charge.
In chemical reactions, bonds break in the reactants and new bonds form
in the products. In homolytic bond cleavage, the bonding electrons are
evenly divided among the two parting atoms; neutral free radicals are the
result. In heterolytic bond cleavage, the bonding electrons are unevenly

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divided between the two parting atoms; charged species, such as

carbocations and carbanions result.

4.2 Sites of Organic Reactions

Organic reactions usually occur at sites within molecules where there is a
special availability or deficiency of electrons. Electrophiles are regions of a
molecule or ion that are positive or deficient in electrons and which tend to attract
electron-rich species and accept electrons in a chemical reaction. Nucleophiles
are electron-rich, provide electrons in a chemical reaction, and tend to attract
electron-deficient or positive species.
A. Multiple Bonds
Double and triple bonds are active reaction sites because they are rich
in electrons and the electrons are accessible due to the nature of pi-bonds.
B. Polar Bonds
Because of the charge separation in polar covalent bonds , they are
common reaction sites since they attract charged species.
C. Lewis Acids and Bases
Nucleophiles and electrophiles are also described as Lewis bases and
acids. A Lewis base is a species that has a non-bonding pair of outer-shell
electrons that can be shared in a chemical reaction. A Lewis acid is a
substance that can accept a pair of electrons for sharing in a chemical
reaction. Nitrogen compounds, such as amines, and oxygen derivatives,
such as alcohols and ethers, are often Lewis bases because the nitrogen
and oxygen have non-bonding electron pairs. Hydrogen ion and simple
boron and aluminum compounds are examples of Lewis acids.
Carbocations are Lewis acids and carbanions are Lewis bases.
D. Combination Reaction Sites
Again, the reaction sites are: multiple bonds (double and triple bonds);
polar bonds; and Lewis acids (electrophiles) and Lewis bases (nucleophiles).

4.3 Getting Started

You might want to organize your study of organic reactions in the following
way:
1. General reaction equation: Identify this as substitution, elimination, or
addition.

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2. Predominant product: Learn to determine this if more than one product is

possible from a chemical reaction.
3. Reaction mechanism: Learn the step by step mechanism in a general way
and understand whether it has carbocations, free radicals, or carbanions as
intermediates.
4. Specific examples: Work specific example problems.

4.4 Halogenation of Alkanes: Chlorination and Bromination

A. General Reaction
Chlorination or bromination of alkanes is an example of a substitution
reaction. A hydrogen on an alkane is replaced by a halogen; hydrogen
halide is the by-product. The reaction is initiated by light or heat.
B. Chlorination of Methane: An Example of Halogenation
Chlorination of methane produces chloromethane, dichloromethane,
trichloromethane, and tetrachloromethane.
C. Control of the Halogenation Reaction
To promote monohalogenation, a high ratio of alkane to halogen is used.
Polyhalogenation is caused using a high ratio of halogen to alkane (at least
as many moles of chlorine as hydrogens in the alkane to get complete
chlorination. Even in monohalogenation, unsymmetrical alkanes yield
multiple products whereas the symmetrical alkanes produce fewer
monohalogenation products.
D. Mechanism of Halogenation
Halogenation proceeds by a free-radical chain reaction mechanism. In
the initiation step, light or heat causes a halogen molecule to dissociate into
free radicals. There are two propagation steps. In one the halogen free
radical abstracts a hydrogen from the alkane leaving a carbon free radical.
In the other, the carbon free radical reacts with a halogen molecule to form a
carbon-halogen bond and a new halogen free radical. The two propagation
steps alternate. The chain reaction can be slowed or halted by chain
termination steps in which free radicals combine to form compounds
without producing a new free radical to continue the chain reaction process.

CONNECTIONS 4.1: Chlorofluorocarbons and the Ozone Layer

CONNECTIONS 4.2: General Anesthetics

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4.5 Preparation of Alkenes and Alkynes: Elimination Reactions

A. General Reaction Equation
Alkenes and alkynes are prepared by elimination reactions in which a
carbon-carbon single bond is converted to a double or triple bond. In
elimination reactions, atoms or groups are eliminated from adjacent carbons.
Elimination once produces double bonds; twice produces triple bonds.
In dehydrohalogenation reactions, hydrogen and halogen are the
atoms eliminated from adjacent carbons. Bases such as potassium
hydroxide and sodium amide are the reagents. Both alkenes and alkynes
can be synthesized by dehydrohalogenation.
In dehydration reactions , the elements of water, H and OH, are
eliminated from adjacent carbon atoms; sulfuric acid is used as a catalyst.
Generally the reaction is only effective in producing carbon-carbon double
bonds.
B. Orientation of Elimination
The Zaitsev rule is used to predict the product of elimination when more
than one product is possible. According to the Zaitsev rule, the most stable
alkene is formed predominantly; this is the one in which the double bond is
most highly substituted with alkyl groups.
C. Mechanism of the Dehydration Reaction
The dehydration reaction proceeds via a carbocation mechanism. The
three step mechanism starts with the protonation of the alcohol oxygen with a
hydrogen ion from sulfuric acid by a Lewis acid-Lewis base reaction. Water
departs in the second step leaving a carbocation intermediate. In the final
step, a hydrogen ion leaves the adjacent carbon and the double bond forms.

Use of Curved Arrows: Curved arrows are used to describe the movement of
electrons in a reaction mechanism. The arrow starts with the electron(s) to be
moved and ends at the atom or bond where they move. Full arrows are used to
denote the movement of electron pairs and fish hook arrows are used to show
the movement of single electrons.

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SOLUTIONS TO PROBLEMS

4.1 Types of Reactions

Double Elimination to Form a Triple Bond

B A B A
C C + 2AB
C C or C C

B A A B

Double Addition to a Triple Bond

B A B A

C C + 2AB C C or C C

B A A B
4.2 Types of Reactions
(a) Addition of HBr to propene

CH3CH CH2 + HBr CH3CH CH2

Br H
(b) Elimination of HBr from 1-bromopropane

CH3CH CH2 CH3CH CH2 + HBr

H Br

(c) Substitution of bromine on propane

CH3CH 2CH 3 + Br2 CH3CHCH3 + HBr

Br
(d) Addition of 2Br2 to propyne
Br Br

CH3C CH + 2Br2 CH3C CH

Br Br

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4.3 Types of Reactions

(a) substitution; (b) elimination; (c) addition;
(d) addition; (e) elimination; (f) substitution

4.4 Addition Reactions

In the addition of HCl to propene, the hydrogen-chlorine bond breaks first. As the
new carbon-hydrogen bond forms, the carbon-carbon double bond “breaks” and
becomes a single bond. Finally, a new carbon-chlorine bond is formed.

4.5 Homolytic and Heterolytic Cleavage

heterolytic cleavage
Br Br Br Br

homolytic cleavage
Br Br Br Br

4.6 Reaction Intermediates

carbocations free radicals carbanions
CH3CH 2CH 2 CH3CH 2CH 2 CH3CH 2CH 2

CH3CHCH3 CH3CHCH3 CH3CHCH3

4.7 Electrophiles and Nucleophiles

(a) Electrophile: incomplete octet of electrons and positive charge.
(b) Nucleophile: complete octet, non-bonding electron pairs, negative charge.
(c) Nucleophile: complete octet, non-bonding electron pairs, negative charge.
(d) Nucleophile: complete octet, non-bonding electron pairs, negative charge.
(e) Electrophile: incomplete octet of electrons and positive charge.
(f) Nucleophile: complete octet of electrons, non-bonding electron pair.

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4.8 Polar Covalent Bonds

(a) O - (b) H + (c)

+ + + + + -
Cl CH2C O CH3 H N CH2CH 2 O H CH3C N
- + + - + - -

4.9 Lewis Acids and Bases

In all of the following cases, the Lewis base site is either a nitrogen with one non-
bonding electron pair or an oxygen with two non-bonding electron pairs. The
presence of a non-bonding pair that can be shared with a Lewis acid (hydrogen
ion in these cases) makes the site a Lewis base.
H
(a) CH3CH 2NH 2 + H+ Cl CH3CH 2NH 2 Cl

(b)
+ H+ Cl Cl
O O
H

O O H
(c)
+ H+ Cl Cl
CH3CCH3 CH3CCH3

(d) CH3C N + H+ Cl CH3C N H Cl

4.10 Lewis Acids and Bases

Boron trifluoride is a Lewis acid because boron has an incomplete octet of
electrons in its outer shell. Ammonia is a Lewis base because it has a non-
bonding electron pair in its complete octet outer shell.

F H F H

F B N H F B N H

F H F H

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4.11 Reaction Sites

polar polar
polar bond bond
bond multiple .. Lewis
bond :O - base + H
+ -
.. + - +
H O CH2CH CH2 CH 3CCH 2CH 2 Br CH 3CH 2CH 2 N H
.. + ++ + ..
-
polar
Lewis Lewis
bond
base base

4.12 Halogenation of Alkanes

light
(a) CH4 + Br2 CH3Br + HBr
light
(b) CH3CH 3 + Cl2 CH3CH 2Cl + HCl

4.13 Chlorination of Ethane

After one hydrogen is replaced by a chlorine, that molecule can compete for
chlorine with the ethane. This can continue to give products ranging from one
hydrogen being replaced to all replaced by chlorine. HCl is the inorganic by-
product.
CH3CH2Cl, CH3CHCl2, ClCH2CH2Cl, CH3CCl3, ClCH2CHCl2,

ClCH2CCl3, Cl2CHCHCl2, Cl2CHCCl3, Cl3CCCl3

4.14 Control of Halogenation

(a) 2-Methylbutane has 12 hydrogens. To replace them all, the chlorine to

alkane ratio must be at least 12:1.

(b) To promote monochlorination, the alkane should be in great excess so that

an attacking chlorine is more likely to interact with an unchlorinated molecule
compared to already chlorinated alkane. There will be unchlorinated alkane left
at the conclusion of the reaction that can fairly easily be separated from the
chlorination product.

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(c) Monochlorination products:

CH3 CH3 CH3
light
CH3CHCH2CH3 + Cl2 CH2CHCH2CH3 CH3CCH2CH3

monochlorination conditions Cl Cl

CH3 CH3

CH3CHCHCH3 CH3CHCH2CH2

Cl Cl
4.15 Free-radical Chain Reaction Mechanism
Initiation Br2 light 2 Br

Propagation CH3CH3 + Br CH3CH2 + HBr

Propagation CH3CH2 + Br2 CH3CH2Br + Br

4.16 Preparation of Alkenes

H2SO4
(a) CH3CH2CH2OH CH3CH CH2 + H2O

aqueous
(b) CH3CH2CH2CH2Br + KOH CH3CH 2CH CH2
alcohol
+ KBr + H2O

aqueous
(c) CH3CH2CHCH3 + KOH CH3CH 2CH CH2
alcohol +
Br CH3CH CHCH3

+ KBr + H2O

4.17 Preparation of Alkynes

(a) ClCH2CH 2Cl + 2 NaNH2 HC CH + 2NaCl + 2 NH3

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(b) CH 3CH 2CH 2CHBr 2 + 2 NaNH2 CH3CH 2C CH

+ 2 NaBr + 2 NH3
Br

(c) CH3CCH 3 + 2NaNH2 CH 3C CH + H2C C CH 2

Br + 2NaBr + 2NH3

4.18 Orientation of Elimination: See Example 4.2

In (a), two alkenes are possible. Concentrate on the carbon with the OH. If the
H on the carbon to the right eliminates, the product is monosubstituted; if the H
on the carbon to the left is eliminated the major product, trisubstituted, is formed.
In (b) a disubstituted alkene is formed if a hydrogen from the carbon to the left of
the carbon-chlorine bond is eliminated. The product shown, which is
tetrasubstituted, is formed if the H on the carbon to the right is eliminated.

a) CH3 b) CH3 CH3

CH3C CHCH3 CH3C CCH3

4.19 Mechanism of Dehydration

CH 3 CH 3 CH 3
H2SO 4
CH 3CCH 2CH 3 CH2=CCH 2CH 3 + CH3C=CHCH 3
predominant product
OH trisubstituted

Reaction Mechanism CH 3

CH 3 CH 3 .. CH 3 CH 2=CCH 2CH 3
H +
-H2O: -H +
CH 3CCH 2CH 3 CH 3CCH 2CH 3 CH 3CCH 2CH 3
+ CH 3
:OH
.. Step 1: :OH Step 2: Step 3:
protonation .. + loss of H 2O; loss of
H carbocation hydrogen CH 3C=CHCH 3
formation ion to form
predominant
alkene
product

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4.20 Polar Bonds: Section 4.2B

-
O Na +
_
CH3CH 2 C N
+
C + +C S -
CH3CH 2CH2CH C N -
CH3 O H
- +

4.21 Lewis Acids and Bases: Section 4.2C

Lewis bases (b and c) have a lone pair of electrons, not used in bonding, which
can be shared with a Lewis acid. Lewis acids usually have an incomplete outer
shell (the Al and B in a and d) and thus can accept the non-bonding electron pair
of a Lewis base.
..
a) Br b) H c) CH3 d) H
..O H
Br Al Br CH3 H B H
.N. CH3
acid base base acid

4.22 Lewis Acids and Bases: Section 4.2C

.. .H. +
a) CH3CH 2
..O H + H+ CH3CH 2 ..O H
b) Cl Cl
Cl Al + .. ..O H Cl Al
-. .. +
.O H
Cl H Cl H
c) H H
+
CH 3 N.
. + HCl CH 3
.
N . H Cl
-

H H

d) CH 3 F CH 3 F
+
. ..
CH 3 N. + B F CH 3 N B F

CH 3 F CH 3 F

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4.23 Reaction Sites: Section 4.2

Lewis
base
.. - polar
O: bond Lewis
base
CH3C(CH2)5 H
-
+ C C + ..
H C O.. H +
multiple ..:
O
polar
bond - bond
Lewis
base

4.24 Electrophiles and Nucleophiles: Section 4.2

(a) nucleophile - negative, non-bonding electron pairs; (b) electrophile -
positive, incomplete octet; (c) nucleophile - non-bonding electron pairs; (d)
nucleophile - non-bonding electron pair; (e) nucleophile - negative, non-bonding
electron pairs; (f) electrophile - positive, carbocation with incomplete octet;
(g) nucleophile - negative, non-bonding electron pair;
(h) nucleophile - negative, non-bonding electron pairs.

4.25 Reactive Intermediates: Section 4.1D

CH 3 CH 3
.
CH 3C. A CH 3C+ A carbocation
+
CH 3 CH 3

CH 3 CH 3
.
CH 3C . A CH 3C. .A free radical
+
CH 3 CH 3

CH 3 CH 3
.
CH 3C . A CH 3C A+
carbanion
+
CH 3 CH 3

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4.26 Reaction Intermediates: Section 4.1D

A+
.. A :C C carbocation
C C +

..
A. C C A :C C. free radical

_
.. A :C C carbanion
A: C C ..
_

4.27 Halogenation of Alkanes: Section 4.4C

CH3 CH3 CH3 CH3 CH3 CH3

a) CH 2CHCH 2CH 2CHCH 3 CH 3CCH 2CH 2CHCH 3 CH 3CHCHCH 2CHCH 3
Cl Cl Cl

Cl
b)

CH3 CH3 CH3 CH3 CH3 CH3

c) CH 2CHCH 2CH 2CCH 3 CH 3CCH 2CH 2CCH 3 CH 3CHCHCH 2CCH 3

Cl CH3 Cl CH3 Cl CH3

CH3 CH3 CH3 CH3

CH 3CHCH 2CHCCH 3 CH 3CHCH 2CH 2CCH 2Cl

Cl CH3 CH3

4.28 Halogenation of Alkanes: Section 4.4C

CH3 CH3 CH3
a) C5H 12 CH3 C CH3 b) C8H 18 CH3C CCH3
CH3 CH3 CH3

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4.29 Halogenation of Alkanes: Section 4.4C

To obtain predominantly bromoethane, use a large excess of ethane relative to
the bromine. Statistically, the bromine is more likely to encounter an ethane
molecule than a bromoethane.

light
CH 3CH 3 (excess) + Br2 CH 3CH 2Br + HBr

To obtain hexabromoethane, provide enough bromine (6 moles) to ensure that

every hydrogen (six) can be replaced.

CH 3CH 3 + 6 Br2 Br3CCBr 3 + 6 HBr

4.30 Halogenation of Alkanes - Reaction Mechanism: Section 4.4D

Initiation Br
.. Br light 2Br.

Br . + CH4 CH 3. + HBr
Propagation
CH 3. + Br2 CH 3Br + Br.

4.31 Halogenation of Alkanes - Reaction Mechanism Section 4.4D

The ethyl radicals formed from the decomposition of tetraethyllead can react
with methane to form methyl radicals or with chlorine to form chlorine radicals.
Both of these are part of the propagation steps.
Initiation
Pb(CH 2CH 3)4 140˚C Pb + 4 CH3CH 2 .
Initiation Initiation
CH 3CH 2 .+ CH4 CH 3CH 3 + CH3. CH 3CH 2. + Cl2 CH 3CH 2Cl + Cl .
Propagation Propagation
CH 3. + Cl2 CH 3Cl + Cl . Cl . + CH4 CH 3. + HCl
Cl . + CH4 CH 3 .+ HCl CH 3. + Cl2 CH 3Cl + Cl .

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4.32 Dehydration of Alcohols: Section 4.5C

H
..
H+ - H2O.. CH 3CH 2CHCHCH 3
CH 3CH 2CHCH 2CH 3 CH 3CH 2CHCH 2CH 3 +
.. OH .. O - H+
.. .. H
from
+ H
adjacent
1. Protonation carbon
2. Loss of water to CH 3CH 2CH CHCH 3
form carbocation
3. Loss of proton to
form alkene

4.33 Elimination Reactions to Produce Alkenes: Section 4.5A-B

Examples a and c are dehydrohalogenation reactions and the others are
dehydrations. The predominant product, when more than one product is
possible, is the most highly substituted alkene. The most substituted alkene is
the one with the most carbons directly connected to the carbons of the carbon-
carbon double bond.
CH3
a) CH3CH CH2 b) CH3CH 2CH CHCH3 c) CH3CH CCH3

CH3 CH3 CH3

d) CH3C CCH3 e) (f) CH2=CH-CH=CH 2
CH3

4.34 Elimination Reactions to Produce Alkynes: Section 4.5A-B

CH3
a) CH3C CH b) CH3CC CH
CH3

4.35 Preparation of Alkenes and Alkynes: Section 4.5A-B

CH3 CH3
Reagent
a) CH 3CHCH 2CH 2 CH3CHCH CH2
X
X = OH Reagent = H2SO4
X = Cl, Br, I Reagent = KOH

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The previous equation is the preferred method for preparing the desired product
since having X on the next carbon would give the most substituted product
predominantly.

CH3 CH3 CH3

Reagent
b) CH 3CHCHCH 2CH 3 CH3C CHCH2CH3 + CH3CHCH CHCH 3
major product minor product
X
X = OH Reagent = H2SO4
X = Cl, Br, I Reagent = KOH

X
c) CH 3CH 2CH 2CH + 2NaNH 2 CH 3CH 2C CH + 2 NaX + 2 NH3
X
X = Cl, Br, I

The other two possible dihalide starting materials are less desirable as they can
give a diene product or 2-butyne as well as the desired 1-butyne.
NaNH2
CH 3CH 2CH CH 2 CH 3CH 2C CH + CH 3CH C CH 2
X X

X
NaNH2
CH 3CH 2CCH 3 CH 3CH 2C CH + CH 3C CCH 3 + CH 3CH C CH 2
X
4.36 Preparation of Alkenes and Alkynes: Section 4.5A-B
(a) Only one product is possible upon dehydrohalogenation of
1-bromopentane and it is not the desired product. Two products can form from
2-chloropentane; the most substituted is the desired 2-pentene and is formed
predominantly.
CH 3CH 2CH 2CH 2CH 2Br CH 3CH 2CH 2CH=CH 2
only product

CH 3CH 2CH 2CHCH 3 CH 3CH 2CH=CHCH 3 + CH 3CH 2CH 2CH=CH 2

major product minor product
Cl

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(b) 1,1-dichloropropane can only form propyne upon dehydrohalogenation. 2,2-

dichloropropane could possibly eliminate in two different directions to give a
diene.

H Cl H Cl H

CH 3C-CH CH3C CH HC-C-CH H 2C=C=CH 2

H Cl H Cl H

(c) Either compound can produce the desired product. The first one can
produce two alkenes whereas the second forms only one, the target compound.
H2SO 4
(CH 3)2CCH 2CH 2CH 3 (CH 3)2C CHCH 2CH 2 + H2O

OH

4.37 Carbocations: Section 4.1D

A carbocation has three bonded groups and is trigonal,

sp2 hybridized, and has 120 o bond angles. The empty
C
orbital is the unhybridized p-orbital.

4.38 Carbanions: Section 4.1D

In a carbanion, there are four space occupying
.. groups - three bonded groups and the
non-bonding electron pair. As a result,
C
it is tetrahedral, sp3-hybridized, and has 109o
bond angles. The non-bonding pair is in an
sp 3 hybrid orbital.

4.39 Lewis Acid, Lewis Base Reactions: Section 4.2C

Cl Cl CH 3
CH 3

Al + O Cl Al O CH 3

Cl Cl CH 3 Cl

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Al: The aluminum in the AlCl3 has three bonded groups and is thus trigonal, sp2-
hybridized and has 120O bond angles. However, in the product the aluminum
has four bonded groups and is tetrahedral, sp3-hybridized, and has 109O bond
angles.
O: In the reactants, the oxygen has two bonded groups and two non-bonding
pairs. In the product, it has three bonded groups and one non-bonding electron
pair. In both cases it has four space-occupying groups and thus is tetrahedral,
sp3-hybridized, and has 109O bond angles.

4.40 Reaction Mechanisms: Section 4.5C

H+ - H2O Br
CH 3CHCH 3 CH 3CHCH 3 CH 3CHCH 3 CH 3CHCH 3

OH OH Br
H
1. Protonation 2. Loss of water to 3. Bromide neutralizes
form carbocation the carbocation

ACTIVITIES WITH MOLECULAR MODELS

1. Make a model of butane. How many different monobromination products are

possible? Make a model of each.

2. Using the models you made in exercise 1 of 1-bromo and 2-bromobutane,

demonstrate the result of dehydrobromination. To do so, remove the bromine
and a hydrogen from an adjacent carbon; insert a double bond between these
two carbons. How many isomers are possible from each compound? Which
is the more stable in the case where two are possible?

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1-bromobutane gives the first product 1-butene as it is the only one possible
from simple elimination. 2-bromobutane, you can see, can give the first
product and the next two, the cis and trans forms of 2-butene. 2-butene is the
more stable product and predominates over 1-butene.

3. Make a model of ethanol and its dehydration product ethene.

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