Lecture 3

1
2) Unsaturated Hydrocarbons

A)Alkenes CnH2n

2
Nomenclature:

1) Choose the longest chain containing the

both carbon atoms of the double bond. 
2) Make numbering from the end that gives
the double bond the least number.
3) Locate the number and name of
substituent.
the priority of functional groups are:
= or > X > alkyl 3
Examples:
1 3-methyl-1-butene
3
2 4

CH2=CH2 Ethylene Ethene

4-If more than one double bond is present the

compound is named as a diene, triene and each
double bond is given its number.
4
 4-methyl-1,4-hexdiene

4 5 Br

5-bromo-1,3-cyclohexadiene
3
2 1
5
Alkenyl radicals Trivial IUPAC

CH2=CH- Vinyl Ethenyl

CH2=CH-CH2- Allyl 2-propenyl

CH3-CH=CH- 1-propenyl

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 CH3 CH2 CH2 CH CH2 CH2 CH2 CH CH3
CH CH3
CH2

The 9-carbon chain is not the parent as

it does not include the double bond
the parent is: 1-octene (not 7-octene)

7-Methyl-3-propyl-1-octene
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 Preparation of Alkenes:
The introduction of carbon-
carbon double bond involves
the elimination of atoms or
groups from 2 adjacent
carbons (i.e.:1,2-elimination)

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 1,2-elimination

Y
β

C C C C + X-Y
α
X
new pi bond XY eliminated
X and Yare eliminated

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When there is more than one beta carbon
atom, more than one beta-elimination
product is possible. Example:
CH3 CH3 CH2
CH3-CH2-C-CH3 CH3-CH2-C=CH2 + CH3-CH2-C-CH3

30%
G these 2 products are the same

+
CH3
70%
CH3-CH=C-CH3

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1. Dehydration of Alcohols:

A. formation of carbocation

protonation: using acid as H2SO4-1

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 H-HSO4
+
OH OH2
-
protonation
CH3-CH2-CH-CH3 CH3-CH2-CH-CH3 + HSO4
heat Oxonium ion

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2- Dehydration:

+
OH2
- H2O +
CH3-CH2-CH-CH3 CH3-CH2-CH-CH3

Oxonium ion heat 2ry carbocation

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 Saytzeff’s rule: (poor get poorer)

States that: “the carbon with the least

number of hydrogens will lose the
proton.”
Elimination occurs to give the more
stable alkene = The more substituted

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3-Deprotonation: according to Saytsef rule: poor gets poorer:

+ -
CH3-CH-CH-CH2 + HSO4 CH3-CH=CH-CH3 + CH3-CH2CH=CH2
H H major minor

+ H2SO4

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 2- dehydrohalogenation (-HX) OF RX : (E2)

Br Br

C C C C C C

H H
Base + Br- + H-B
Base

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2- dehydrohalogenation (-HX) OF RX : (E2)

alc. KOH, alc. NaOH

or
potassium ethoxide CH3CH2O- K+
or
NaOEt
CH3-CH-CH3

Br

CH3-CH=CH2

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2- Reagent :
Is a base to abstract H as a proton . Such as: alcoholic KOH,
Alcoholic NaOH, NaOC2H5 (In ethanol),

(all are strong bases in alcohol)

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3- we apply saytzeff’s rule (poor gets poorer)
CH3CH2O- K+
e.g. CH3-CH-CH2-CH3 CH3CH=CHCH3 +CH2=CHCH2CH3
Br major minor

4-The order of reactivity of alkyl halides toward E reactions is

R-I>R-Br>R-Cl>R-F.
the order of reactivity of alkyl halides towards E reaction is-5

3°RX>2°RX>1°RX
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3- debromination of vicinal dihalides:
Br
Vicinal -C-C- geminal CH3-C-CH3
Br Br Br

Zn/acetic acid
C=C
e.g. -C-C-
Br Br

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 H3C CH3

CH3
H3C
H3C

H3C

23
H3C

H3C

3,3-dimethylcyclopentene 24
 Physical Properties:

Alkenes are non-polar, slightly

more soluble in H2O than
corresponding alkanes.

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 Reactions:
1. Reactions at the C=C bond.
2. Reactions at certain positions having
special relationship to the double bond
(Allylic halogenation).
Vinylic
carbon Allylic carbon
C═C-C-
(free radical
H substitution)
(Addition,
reduction,
oxidation)
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