CHEMISTRY OF THE ALKENES

The alkenes are unsaturated hydrocarbon with one or more double bonds in their molecule. The
general molecular formula of alkenes with only one double bond is C nH2n where n is a positive whole
number equal to or greater than 2.

They are also called olefins. Alkenes and cycloalkane have the same general molecular formula
(that is alkenes are isomeric with cycloalkanes). But while alkenes are acyclic, cycloalkanes are
alicyclic.

Table 2.1 some members of the normal alkene series

Name and molecular formula Structural Formula Name
Ethene C2H4 CH2=CH2 Ethene
Propene C3H6 CH3CH2= CH2 Propene
Butene C4H8 CH2= CHCH2CH3 But-1-ene
Butene C4H8 CH3 CH= CHCH3 But-2-ene
Pentene C5H10 CH3CH2 CH= CHCH3 Pent-2-ene

When compared with the alkanes, the alkenes burn with a more smoky and luminous flame because
they contain a greater proportion of carbon. Also they are much more reactive than the alkanes
because of the presence of double bond. As the sizes increase, the melting and boiling points
increase due to increase in the vander Waal forces. Also, branched isomers have lower boiling
compared to straight chain isomer because branching makes the molecle more loosely packed. And
as such the more the branching the lower their boiling point.

NOMENCLATURE OF ALKENES
Alkenes are named as if they were alkanes, but the "-ane" suffix is changed to ene".
butane: C4H10 (CH3CH2CH2CH3)
butene: C4H8 (CH2= CH2CH2CH3)

Correct: pent-2-ene (CH3CH=CHCH2CH3)

Incorrect: pent-3-ene (CH3CH2CH=CHCH3)
The second one is incorrect because flipping the formula horizontally results in a lower number for
the alkene.

1
octa-2,4-diene: CH3CH=CHCH=CHCH2CH2CH3
deca-1,5-diene: CH2=CHCH2CH2CH=CHCH2CH2CH2CH3

METHODES OF PREPARATION
1. REDUCTION OF ALKYNES (HYDROGENATION OF ALKYNE)
Recall that as discussed earlier in module 1, catalytic hydrogenation of alkyne in the presence
of a metal catalyst yields alkane via the alkene intermediate which cannot be isolated.

RC ≡ CR + H2 Pt or Pd or Ni
RCH= CHR

RCH = CHR + H2 Pt or Pd or Ni
RCH2 CH2R

Overall reaction
RC ≡ CR + 2H2 Pt or Pd or Ni
RCH2= CH2R

C2H5 C ≡ CC3H7 + 2H2 Pt or Pd or Ni

C2H5 CH2 CH2 C3H7
In order to prepare alkene by reduction`n of alkynes, a less effective catalyst such as Lindlar’s
catalyst is used. Lindlar’s catalyst is prepared by poisoning (deactivating) the conventional
metal catalyst (Pt, Pd, Ni, etc) with lead acetate and quinoline. This allows alkyne to be
converted to alkene without further reduction to alkane. Lindlar’s catalyst is specifically used
to prepare cis – alkenes

Trans- alkenes are prepared by reducing the alkynes in the presence lithium or sodium metal in
liquid ammonia (or ethylamine) at low temperatures.

2. ELIMINATION REACTION
Generally alkenes are prepared by β elimination reactions (1, 2-elimination), where two
atoms from adjacent carbons are removed, resulting to the formation of a double bond.
Some of these methods are discussed:

i. Dehydration of monohydric alcohols

2
Alkene can be prepared by heating alcohol in the presence of concentrated tetraoxosulphate
(VI) acid at 1800C. The reaction two-stages;
The first stage takes place in the cold, and it involved formation of the ester, alkyl
hydrogentertraoxosulphate (VI) by treating ethanol with the acid at volume ratio of 1:2

The second stage involves the decomposition of alkyl hydrogentetraoxosulphate (VI) by heating in
excess concentrated tetraoxosulphate (VI) acid to produce alkene.

The overall reaction involves the removal of one molecule water from alcohol by hot concentrated
tetraoxosulphate (VI) as the dehydration of ethanol.

ii. Dehydrohalogenation of haloalkanes

The β elimination (1, 2-elimination) which could be an E1 or E2 reaction involves the
removal of a hydrogen atom and a halide from adjacent carbons in a haloalkane.

The reaction also follow saitsev rule which state

that during β- elimination, the more substituted
product is the major product. The elimination also involves
anti-elimination that is the removal of β-hydrogen and the halide ion occurs from opposite
sides.

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iii. Dehalogenation of dihaloalkanes
Dehalogenation of vicinal dihalide (haloalkane were the two halogen atoms are on adjacent carbon
atoms) yields alkene.

3. KOLBE’S ELECTROLYTIC METHOD

The electrolysis of sodium or potassium salts of dicarboxylic acids produces symmetrical alkenes
The electrolytic proceed through a free radical path way.

At the anode

At the cathode

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Physical Properties
The first three members are gases, next members are liquids. They have similar melting and
boiling points to the alkanes.
Melting also increases as the family descends as members with higher molecular weight have
higher melting points.
Branching also lower boiling points compare to linear isomers.

CHEMICAL PROPERTIES
Alkenes are more reactive than the alkane because of their double bond which allows them to
undergo mainly addition reactions.

Addition Reactions
Because alkenes are unsaturated, their most important reactions are electrophilic addition reactions.
Alkenes undergo addition reactions with a variety of reagents of the general type A- B.

In this kind of reaction the double bond is broken and the electrons are used to form two single
bonds with two new atoms. The general reaction is shown by the equation:
This reaction can often be reversed in an elimination reaction to produce an alkene.

The general mechanisms involve two steps;

1. The first step is the reaction of the carbon-carbon double (C=C) bond with the electrophile to
produce a carbocation. The reaction of the electrophile with the alkene dictates the
regioselectivty. There is also the rearrangement of the carbocation to give the more stable
carbocation.

2. The second step is the attack of the nucleophile to form the addition products.

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The whole reaction involves breacking of the C=C and the formation of two sigma (σ)
bonds, although there might slight modification in the mechanism depending on variations in
type of reagents and experimental conditions.The following are examples of addition
reactions of ethene.
1. Addition of Hydrogen (hydrogenation)
Hydrogenation of alkene takes place by reacting with hydrogen (H 2) in the presence of a catalyst.
This process is called catalytic hydrogenation. Catalysts that are generally used are transition metals
(platinum, rhodium, ruthenium or nickel

RCH = CH2 + H2 Pt or Pd or Ni
RCH2 CH3

CH3CH = CH CH2H5 + H2 Pt or Pd or Ni
CH3CH2 CH2 C2H5
The reaction is also used in the production of margarine.
2. Addition of Halogens (halogenation)
Alkenes reacts with bromine and chlorine at room temperature in the presence of a solvent
such as tetra chloromethane (CCl4) give vicinal - dihaloalkane.

3. Addition of Hydrogen Halides (hydrohalogenation)

Alkenes react readily with the hydrogen halides (HCI, HBr, or HI) in an electrophilic
addition to give haloalkane. Hydrogen fluoride is not reactive with alkenes. The order of
reactivity of hydrogen halide is HCI > HBr > HI).

The mechanism of the reaction proceeds by two steps;

Step 1: This involves the protonation of the alkene to form the most stable carbocation

Step 2: Then is the attack of the electrophilic carbon by the halide nucleophile to gives the final
chloroalkane.

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The reaction is regioselective that follows Markovnikov rule. The rule states that when an
asymmetrical electrophilic reagent such as HX, H2O, XOH or H2SO4 adds to an
asymmetrical alkene, the hydrogen (or the positive end of the addendum) adds to the
carbon atom of the double bond that holds more hydrogen. Another example is giving
below;

The reason for this is because of the stability of carbocations.

Tertiary carbocations are the most stable and form faster than secondary carbocations, which are
more stable and form faster than primary carbocations (order of stability is 30 > 20 > 10 > CH3).

This is a general order with carbonations which are very common intermediates and will be
encountered as we proceed in this course. In the presence of peroxide addition of HBr to alkenes
follows the anti Markvonikov rule as a result is called the peroxide effect.
4. Addition of hypohalous acids (HOX or bromine and chlorine water or halohydration)
to form halohydrins
This reaction is also called the addition of halogen and water because it is not the direct
addition of hypohalous acids to the alkene. The reaction is similar to the addition of halogen
acids (HX) but in the case, after the alkene has reacted with the aqueous solution of the
halogen first, it is then followed by the reaction with water in accordance with Markovnikov
rule. Here, the halogen ions (Br+ or Cl+) are the electrophiles while the hydroxide ion (OH-)
is the nucleophile. Reaction of the alkene with chlorine water gives chlorohydrins.

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Reaction with bromine water gives an instant discharge of the brown coloure of the
bromine to form bromohydrin. This decolourisation of bromine water is used to distinguish
unsaturated hybrocarbons from saturated hydrocarbons.

5. Addition of water (hydration of alkene)

Acid catalysed hydration of alkene results to the formation of alcohol and the addition
also follows Markovnikov’s rule.

That is it involves the protonation of the alkene by the acid to give the most stable
carbocation. This is followed by the attack by the nucleophile (water) to produce an
oxonium ion. And finally is the loss of proton to give the alcohol and the acid catalyst is
regenerated.

6. Reaction with potassium tetraoxomanganate

EthEne reacts with acidified potassium tetraoxomanganate (VII) (KMnO 4) solution to give a
dihydroxyl derivative (also called glycol or diol). In the process, the double bond is broken
with the addition of two OH groups across the carbon-carbon double bond.

8
This is another test for the presence of a double bond as the diol forms in that position and
the purple colour of the potassium tetraoxomanganate (vii) solution.
(KMnO4) discharges.

7. Reaction with concentrated tetraoxosulphate (VI) acid

Alkenes react with concentrated tetraoxosulphate (VI) acid in the cold to form alkylhydrogen
tetraoxosulphate (VI) which is an ester of sulphuric acid.

the hydrogen ions (H+) is the electrophiles while the hydrogensulfate ion (-OSO3H) is the
nucleophile

When the resulting mixture is boiled with water it undergoes hydrolysis and alcohol is form.
The reaction is actually the reverse process for the preparation of alkene.

8. Polymerization (self addition)

Polymerization is a process by which an organic compound reacts with itself to form a high-
molecular-weight compound composed of repeating units of the original compound. The
polymerization of ethene is an ionic or free-radical reaction. In this reaction, ethane add to itself in
the presence of high temperature and pressure, using dibenzene peroxide (C6H5CO2) as catalyst
nCH2=CH2 2000atm [-CH2-CH2- CH2-CH2-]
9. Epoxidation of Alkenes

This is the oxidation reaction of alkenes with peracid (also called peroxyacid) ( ) to
form three-membered cyclic ethers known as epoxide.

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10. Ozonolysis of Alkenes
Ozone cleaves carbon-carbon double bonds to give two carbonyl compounds.

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The intermediate in this process is a 5 membered ring called an ozonide. Ozonides are
unstable, explosive compounds and are usually reduced to the carbonyl compounds
with zinc in acetic acid, triphenylphosphine, or dimethylsulfide.

Under these reductive conditions, the products of the reaction are aldehydes and/or
ketones. The reaction is used as a synthetic route to carbonyl compounds

Under non reductive conditions aldehydes are not isolated but are oxidized to
carboxylic acids. Ozonolysis is used as a synthetic route to carbonyl compounds

11. Alkoxymercuration-demercuration of alkenes

Alkenes react with mercuric trifluoroacetate and alcohol in the presence of
tetrahydrofuran as solvent in a process called alkoxymeruration to give
alkoxyalkylmercury compounds.
 Alkoxymeruration

 Demercuration

1. Oxymecuration – demecuration reaction ( formation of alcohol)

This reaction is an alternative method of hydrating alkenes into alcohols. Alkenes
undergo oxymecuration reaction with mercury acetate, using tetrahydrofuran (THF)
as solvent to produce hydroxylmercurial compounds. Reductive cleavage of the
hydroxylmercurial compounds with sodium borohydride as the reducing agent gives
alcohol. The reductive cleavage reaction is called demercuration. The overall reaction
is the hydration of alkenes in accordance to Markkovnikov rule.

Oxymecuration reaction

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The advantage of this reaction is that it can be used to prepare the desired product (alcohol)
because the reaction does not involve carbocation rearrangement. For example, hydration of
3-methylbut-1-ene will result to the formation of 2-methylbutan-2-ol while Oxymecuration –
demecuration of it will give 3-methylbutan-2-ol. Unfortunately, care should be taken with the
reaction as mercury compounds are generally quite toxic.
Hydration of 3-methylbut-1-ene

Oxymecuration – demecuration reaction of 3-methylbut-1-ene

Also, hydration of 3,3-dimethylbut-1-ene yield 2,3-dimethylbutan-2-ol while Oxymecuration

– demecuration reaction of it gives 3,3-dimethylbutan-2-ol.
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2. Combustion
Like methane, ethane burns in air or Oxygen to give carbon (iv) oxide and water. But ethane
contains more carbon in proportion to hydrogen than the corresponding alkane, therefore it
burns with a smoky luminous flame. This is due to the insufficiency of Oxygen in the
surrounding air to completely burn it.
TEST
Unsaturated hydrocarbon (alkene and alkyne) decolourises the brownish colour of
bromine in a mixture of bromine and CCl4.
Also, the purple colour of KMnO4 is discharged by reacting with unsaturated
hydrocarbon (alkene and alkyne). In the reaction bromine and hydroxyl are added
respectively to the double bond.

USES OF ALKENES
1. Used in the manufacture of the plastic polyethylene, polypropylene and chloride
(PVC).

2. The release of ethylene stimulates the ripening process in many plants some plants
can be picked while unripe (when they are less fragile), and exposed to ethylene gas
to cause ripening once they reach their destination

3. Tetrachloroethylene (also known as perchloroethylene (“Perc”)) a nonflammable

organic solvent, widely used in dry cleaning; it is also used as an industrial solvent,
degreaser, and paint remover.

4. It is starting material for making compounds like ethane, ethanol, ethanoic acid, etc.

REVIEW QUESTIONS
1. Alkenes may have cis and trans isomers. Draw and identify the cis and trans isomers
of 3-heptene

2. With suitable examples explain the following;

i. Markovnikov's rule
ii. Saitsev’s rule

3. Write down the structures of the following organic compounds;

i. 2,3,4-trimethylpentene
ii. 2,3-dimethylpenene
iii. 3 - ethyl-2- methylhex-2- ene

4. Suggest product formed on the following reaction of but-1-ene

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i. Ozonolysis
ii. Hydrogenation
iii. Chlorination
iv. Hydration
v. Hydrochlorination

5. Give the structural formula and correct IUPAC name of compound formed by the
dehydration of
(a) 2-methylbutanol (b).2,3- dimethylpentan-2-ol

6. Give the products formed on hot permanganate cleavage of the following compounds
(a)(CH3)2C=C(C2H5)2 (b) CH2=CHCH3

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CHEMISTRY OF THE ALKYNES

The alkynes have general molecular formula of CnH2n -2 where n equals to or greater than two.
The simplest member of family is ethyne (also known as acetylene), has two carbon atoms
and the molecular formula of C2H2. The structural formula for ethyne is H- C≡C-H

They undergo addition reaction where atoms are added across the triple bond.

. In alkynes of four or more carbon atoms, the triple bond can be located in different
positions along the chain, leading to the formation of structural isomers. For example, butyne
C4H6 has two isomers,
HC≡C-CH2CH3 and CH3—C≡C-CH3
NOMENCLATURE OF THE ALKYNE
The following rules summarize alkyne nomenclature.
1. Identify the longest continuous chain that contains the carbon- carbon triple bond and
name as the parent chain. As an illustration the compound below has five carbon
atoms containing a triple bond. Thus the compound has pentyne as the parent chain.

CH3 —CH2—C≡C—CH3

2. Number the carbon atoms of the longest continuous chain, starting from the end
closest to the triple bond. Numerical value is given to the position of the triple bond.
The value of the triple bond here is 2 and not 3.

Correct: 4-methylpent-2-yne
Incorrect: 2-methyl pent-3-yne

3. Label each of the substituents at its equivalent carbon but arrange them in alphabetical
order. Prefixes such as di-, tri-, tetra- etc are used to indicate substituents that appear
twice, three times or four times as the case may be, but not placed alphabetically.

4. In naming the alkynes, the number should precede the "yne" suffix with a dash, as
shown below is given by first writing the numeric positions of all the prefixes, while
the name of the suffix comes last

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5. Molecules that contain both a double and a triple bond are numbered in a manner that
gives the first multiple the lowest number. But if both bonds can be assigned the
same number, then the double bond is given the priority. However, the molecule is
named "n-ene-n-yne", with the double bond root name preceding the triple bond root
name (e.g. 2-hepten-4-yne).

METHODS OF PREPARATION
The preparations of alkynes are very similar to those of the alkenes. The main preparative
reactions involve the elimination of groups or ions from molecules, resulting in the formation
of a π bond. Some of the preparative methods are discussed;
1. DEHYDROHALOGENATION OF DIHALOALKANES: The loss of a hydrogen
atom and a halogen atom from adjacent carbon atoms in alkane leads to the formation
of an alkene.

The loss of additional hydrogen and halogen atoms from the double-bonded carbon atoms
leads to the formation of alkyne.

The halogen atoms may be located on the same carbon (a geminal dihalide) or on adjacent
carbons (a vicinal dihalide).

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2. DEHALOGENATION VICINAL TETRAHALOALKANES: Dehalogenation of
vicinal tetrahaloalkanes by heating with zinc dust in ethanol forms alkynes.

The limitation of using haloalkanes in preparing unsaturated hydrocarbon is that the

haloalkanes are first obtained from halogenating unsaturated hydrocarbons. Thus it is like
going back and forth.

3. FROM CALCIUM CARBIDE: Ethyne, which is commonly called acetylene, is the

simplest alkyne. In the past, it was prepared by reacting calcium carbide with water.
CaC2 + 2H2O Ca(OH)2 + HC≡CH
Nowadays, ethyne is normally prepared by the pyrolysis of methane. In this procedure, a
stream of methane gas is briefly heated to 15000C in an airless chamber. Air must be
excluded from the reaction or oxidation (combustion) will occur.
2CH4 15000C 2HC≡CH + 2H2
0.1amt

REACTIONS OF THE ALKYNES

1. ACIDIC PROPERTIES OF ALKYNES (SUBSTITUTION REACTION)

The hydrogen attached to triple bonded carbon can be readily abstracted by a very strong
base indicating that it is slightly acidic. This explains the weakly acidic properties of
terminal alkynes. The carbon atom in alkynes are sp hybridized with a greater s- character as
compared to the alkenes (sp2 hybridized) and alkanes (sp3 hybridized) thus making it more
electronegative. As a result, the shared electrons pair of the C-H bond is attracted highly
towards the carbon in a manner that hydrogen becomes electron deficient. And thus can be
easily abstracted by a strong base.
Therefore, alkynes react in a substitution reaction with strong bases such as sodium, copper
(I) chloride and silver nitrate in ammonia to give their corresponding acetylide and liberated
hydrogen (H2) gas. But such reactions will not happen in alkanes and alkenes. The conclusion
is that the hydrogen atoms attached to the carbon-carbon triple bond in alkynes are slightly
acidic in nature.
Ethyne reacts in a substitution reaction with sodium in liquid ammonia (or sodium amide) to
give sodium acetylide

The acetylide formed can be used to prepare higher alkynes by reacting it with the
appropriate haloalkane.
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Terminal alkynes (alkynes with acidic hydrogen) forms red precipitate of cuprous acetylide
and white precipitate of silver acetylide by reacting with ammoniacal solution of copper (I)
chloride and sliver nitrate respectively. Since internal alkyne do not undergo this reaction it
can therefore be used as a test to distinguish internal alkynes from internal alkynes.

2. ADDITION REACTION OF ALKYNE

Since the most common chemical reaction of a carbon- carbon double bond is
addition reaction, we might expect the same to be true for carbon-carbon triple bonds
since they are both unsaturated hydrocarbons. Indeed, most of the alkene addition
reactions discussed earlier also takes place with alkynes and with similar regio- and
stereoselectivity.

i. Hydrohalogenation of the alkyne

Adding a halide acid such as HCl or HBr to an alkyne can create a geminal dihalide via a
Markovnikov process. The reaction takes place in two stages – first is the addition of one
mole of hydrogen halide to give the double bond derivative and next is the addition of
another mole of hydrogen halide to give the alkane derivative. If the reaction is carried out in
the presence of Hg2+ as catalyst it is stopped at the alkene derivative. Also, adding HBr in the
presence of peroxides results in the Anti-Markovnikov alkenyl bromide product.

ii. Hydration of Alkynes and Tautomerism

As with alkenes, the addition of water to alkynes requires a strong acid, usually sulfuric acid,
and is facilitated by mercuric sulfate. However, unlike the additions to double bonds which
give alcohols, alkynes give ketone products (except for acetylene which yields acetaldehyde).
The explanation for this deviation lies in enol-keto tautomerization. The initial product from
the addition of water gives an enol (a compound having a hydroxyl substituent attached to a
double-bond). This is followed by an immediate rearrangement of the enol to give a more
stable keto tautomer.

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Tautomers are defined as rapidly interconvertable constitutional isomers, usually
distinguished by a different bonding location for a labile hydrogen atom and a differently
located double bond. The equilibrium between tautomers is not only rapid under normal
conditions, but it often strongly favors one of the isomers (acetone, for example, is 99.999%
keto tautomer). Addition of water follows the Markovnikov’s rule for terminal alkynes while
addition of water to internal alkynes is not regioselective. Also, if the triple-bond is not
symmetrically located (i.e. if R and R1 are not the same) dtwo isomeric ketones will be
formed. Therefore, apart from acetelyne which can be hydrates in to acetaldehyde, terminal
alkynes are hydrated into ketones. Also, terminal and symerical alkynes give only one
product while other alkynes give a mixture of products.

iii. Halogenations of the alkyne

Alkynes react with halogens also in two steps. First forming the dihalide and next the
tetrahalide. The reaction with chlorine is explosive in the presence of sunlight and without a
catalyst. Reaction with bromine is less explosive. The reaction is carried out in the presence
metallic halide as catalyst. Reactivity follows the order Cl2 > Br2 > I2.

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iv. Catalytic Hydrogenation
Hydrogen adds across carbon-carbon triple bonds at room temperature in the presence of
platinum or palladium catalyst both of which must be finely divided. Nickel catalyst can also
be used only at high temperature. (250 – 3000C). The reaction proceeds via alkene formation.

RC ≡ CR + H2 Pt or Pd or Ni
RCH= CHR

RCH = CHR + H2 Pt or Pd or Ni
RCH2 CH2R

Overall reaction
RC ≡ CR + 2H2 Pt or Pd or Ni
RCH2= CH2R

C2H5 C ≡ CC3H7 + 2H2 Pt or Pd or Ni

C2H5 CH2 CH2 C3H7
In order for the reduction to stop at alkene, a less effective catalyst such as Lindlar’s
catalyst is used. Lindlar’s catalyst is specifically used to prepare cis – alkenes

Trans- alkenes are prepared by reducing the alkynes in the presence lithium or sodium
metal in liquid ammonia (or ethylamine) at low temperatures.

v. Polymerization

Alkynes can undergo linear and cyclic polymerization under suitable conditions. Linear
polymerization can be achieved when ethyne dimerises in the presence of acidified solution
of copper (I) chloride in ammonia as catalyst to give but- 1-en-3-yne.

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For cyclic polymerization high temperatures and the presence of a catalyst is required. This
can be achieved by passing ethyne through a heated tube at 4000C to give benzene.

At the same reacting condition propyne gives 1,3,5-methylbenzene.

3. COMBUSTION
Ethyne burns in air with a luminous, very sooty flame and an enormous release of
heat (30000C). The sooty flame is as a result of it very high level of unsaturation (high
carbon content). The large release of heat as it burns makes it useful in oxyacetylene
flame for welding and cutting metals.

TEST FOR ALKYNES

1. Unsaturated hydrocarbon (alkene and alkyne) decolourises the brownish colour of
bromine in a mixture of bromine and CCl 4. Also, the purple colour of KMnO4 is
discharged by reacting with unsaturated hydrocarbon (alkene and alkyne). In the
reaction bromine and hydroxyl are added respectively to the double bond.
2. Alkynes with acidic hydrogen forms alkynides with ammoniacal solution of copper
(I) chloride (red precipitate) and silver nitrate solution (white precipitate). The
reaction is used distinguish terminal alkyne from internal alkynes. Internal alkynes
that do not undergo the reaction
USES OF ALKYNES
1. Alkynes are used as synthetic routes to other chemical reagents such as alkanes,
alkenes, haloalkanes, alcohol, aldhydes, ketones, etc
2. Ethyne is used in oxyacetylene flame for welding and cutting metals.

REVIEW QUESTIONS
1. Draw and name all possible structural isomers with the formula C8H14

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2. Draw the Structures of the following

i. 5-chloro-2-hexyne.
ii. 4-methylpent-2 - yne
iii. 3-methylbut-1-yne
iv. 4,5-dimethylhex -2-yne

3. Suggest IUPAC name for the following alkyne

i. CH3CH2C≡CHCH3
ii.CH≡CCH2CH2CHBr2
iii. CH3CH2CH2 C (CH3)2C≡CCH3

3. Explain how one can distinguish between saturated and unsaturated hydrocarbon
in the laboratory, subsequently show how one can distinguish between the
terminal and internal alkynes

5. Compound (CH), gives a precipitate with Ag(NO3)2; decolourizes bromine water

and yield propanoic acid with hot KMnO4. Hydrogenation of CH gives C4H8, further
hydrogenation yeildsC4H10. Write the structure and suggest IUPAC name of CH.

6a. Suggest mechanism for the dehydration of CH3CHOHCH3

b. Give the structural formulas of the major prodcuts formed from the reaction of 2,3-
dimethyl-2-pentene by;
i. Bromination ii. Hydrobromination iii. Hydration
iv. Combustion v. Hydrogenation

7. Give the structural formulas for the alkenes formed on dehydrobromination of the
following bromoalkanes;
i.1 – bromobutane
ii. 2 – bromobutane
iii. 3 – bromobutane
iv. 2 – bromo -2- methylpentane
v. 3 – bromo -2- melthylpentane
vi. 3 – bromo -2, 3- dimethylpentane

8. Suggest how 3, 4-dimethyl -1-pentyne can be prepared from an appropriate organic

compound

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