ABDULRAHMAN AL-SUMAIT UNIVERSITY

DEPARTMENT: SCIENCE DEPARTMENT

COURSE TITLE: ORGANIC CHEMISTR- 1

COURSE CODE: CH 112

COURSE INSTRUCTOR: SALIM A. SALIM

GROUP NUMBER: 02

TYPE OF ASSIGNMENT: GROUP ASSIGNMENT

ACADEMIC SEMISTER: FIRST SEMISTER

No STUDENT NAMES REGISTRATION NUMBER

1 TWAHIR KHAMIS ALI 19/PC/004
2 WAHIDA NASSOR HAMAD 19/BC/003
3 HIDAYA SHAABAN BAKAR 19/BC/023
4 SULEIMAN YUSSUF KHAMIS 19/BC/024
5 SAFINIYA SOUD MOH’D 19/BC/049
6 ISSA KHALFAN RASHID 19/BC/022
7
8

QUESTION: Discuss the cycloalkanes

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 CYLOALKANES

Many organic compounds are cyclic. They contain a ring of atoms. The

Carbohydrates we eat are cyclic, the nucleotides that makes up our DNA and RNA

are cyclic and the antibiotics we us to treat diseases are cyclic.

Cycloakanes are alkanes that contain rings of carbon atoms. Simple cycloalkanes

are named like acyclic(non cyclic) alkanes, with the prefix cyclo- indicating the

presence of ring. Example cycloalkanes. Line angle formulas are often used for

drawing the rings of cycloalkanes.

GENERAL MOLECULAR FORMULAR OF CYCLOALKANES

Simple Cycloalkanes are ring of CH2 groups (methylene group). Each one has

exactly twice as many Hydrogen H atoms as Carbon atoms, giving the General

Molecular Formula (GMF) CnH2n .This GF has two fewer H atoms than the (2n+2)

for molecular formula for acyclic alkanes because the rings has no end and no

Hydrogen are needed to cap off the ends of the chain.

PREPARATION OF CYCLOALKANES

Following methods are commonly used for the preparation of cycloalkanes.

(a) From dihalogen compounds : α-ω elimination from dihalides having halogen
atoms on two ends of carbon chain (α-ω dihalides) with Na or Zn dust gives rise to
the formation of cycloalkanes. The method can be regarded as intramolecular

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Wurtz reaction and is called Freund reaction. This can be used to prepare
cycloalkanes from three to six carbon atoms.

(b) By Clemmensen reduction : The reduction of cyclic ketones by Zn-Hg/HCI

gives cycloalkanes.

  

c) From alkenes : Alkenes on treating with CH2I2 in presence of Zn-Cu couple or

by diazomethane (CH2N2) in presence of U.V. light gives derivatives of
cycloalkanes.

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(d) By Dieckmann cylisation: Esters of dicarboxylic acids on heating in presence
of sodium ethoxide undergo intramolecular Claisen condensation to gives cyclic β-
keto esters. These β-keto esters on hydrolysis and subsequent heating gives cyclic
ketones which are reduced by Zn-Hg/HCI to give cycloalkanes.

(e) From aromatic compounds: Six membered cyclo compounds can be easily

obtained by the catalytic reduction of benzene and its derivatives.

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NOMENCLATUTE OF CYCLOALKANES

Cyloalkanes are named much like linear chain alkanes.Subtituent cycloalkanes use
use the cycloalkanes for the base name, with the alkyle groups named as
subsituent.

 If there is just one subsituent, no numbering is needed. Examples

CH3
CH3 H3C
CH3

Methylcyclopentane t-dimethylcyclohexane

 If there are two or more substituent on the ring, the ring carbon are
numbered to give the lowest possible numbers. The numbering begin with
one the substituted ring carbons and continue in the direction that gives the
lowest numbers to the other substituent. In the name, the substituents are
listed in alphabetical order, and always begin with one that is alphabetically
first. Examples
CH3 CH3
H3C

H3C CH3

1-ethyl-2-methylcyclobutane 1,1,3-trimethylcyclopentane

CH3

H3C
CH3

CH3

1,1-diethyl-4-isopropylcyclohexane

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  When acyclic portion of the molecule contains more carbon atoms, the
cyclic portion(when it contain an important group) the cyclic portion is some
time named as cycloalkyl subsituent.

HC

CH3

H3C
4-cyclopropyl-3-methyloctane 5-cyclobutyl-1-pentyne

Cyclopentylcyclohexane

PHYSICAL PROPERTIES OF CYCLOALKANES

Most cycloalkanes resemble the (non cyclic), open- chain in their physical
properties and their chemistry. Cycloalkanes are alkanes in the form of a ring
which show various physical properties such as follow:

 The first four members of cycloalkanes are existing in liquid in gaseous

form, the next four members exit in liquid form and the longest chains
remain exit in solid form.
 Solubility: Cycloalkanes are nonpolar and hydrophobic so they dissolved in
nonpolar solvent such as toluene, ether and others. Cycloalkanes are good
lubricants and ------- for metals and keep water from ---- the metals surface
and causing corrosion. Density; Cyloalakanes are less dense than water so
form mixture known as sublimation.
 Boiling point: Boiling point of cycloalkanes increases smoothly with
increasing number of carbon atoms and the increasing molecular weight, this
result large surface area and create intermolecular vand Waals attraction to

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 increase. So molecules of Cycloalkanes collide more each other and also
temperature increasing and at the end the boiling point increasing.
 Melting point of Cycloalkanes; is also equal to the boiling point means that
the melting point of Cycloalkanes increasing when the number of carbon
increasing. But also branching Cycloalkanes affect melting point means that
have large melting point compared to UN branched cycloalkanes which have
the same number of Carbon.

CHEMICAL PROPERTIES OF CYCLOALKANES

Addition reaction

Cycloalkanes with small rings tend to undergo addition reactions, the result of
which is to rupture the cyclic system and form linear chain and their derivatives. In
the absence of UV light, cyclopropane can undergo addition reactions in which the
ring is broken. For example, with bromine, cyclopropane gives
1,3-dibromopropane. Examples;

This can still happen in the presence of light - but you will get substitution
reactions as well.

The ring is broken because cyclopropane suffers badly from ring strain. The bond
angles in the ring are 60° rather than the normal value of about 109.5° when the
carbon makes four single bonds.

The overlap between the atomic orbitals in forming the carbon-carbon bonds is less
good than it is normally, and there is considerable repulsion between the bonding
pairs. The system becomes more stable if the ring is broken.

Free Radical Substitution Reaction

Cyclopentanes, cyclohexanes, and the remaining higher cycloalkanes undergo

Subtitution reaction like open chain alkanes. However they are not broken open
during the reaction. This shows their stability. Examples

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+ Br 2 Sr ,300 + HBr
→

Oxidation Reaction

The cycloalkanes are not oxidized either by Potassium permanganate (--the

alkanes). Even the relatively reactive cycloalkanes (cycloalkanes & cyclobutanes)
are resistant to oxidation by these reagents. However under extreme conditions the
rings can be broken open to give a dicarboxylic acid. This involves the air-
oxidation of cycloalkanes over a Cobalt catalyst.

Examples

Nitration reaction

Five and six member cycloalkanes can be nitrated to give Nitroalkanes. Examples;
O
+
+ HNO3 400 ℃ N
-
→
O

Common Uses
Some uses are given below-

 In the medical applications, cycloalkanes are used as an organic solvent in

the production of drugs
 These are utilized in the manufacture of hair products as well as in the food
industries
 The cycloalkane called cyclopropane is used as an anesthetic agent in
medical field
 Carboplatin which is derived from the cyclobutane is used to treat cancers
 They are also employed in the petroleum industries.
 Some of the classes of cycloalkanes are used for pigmentation purposes and
also used as fragrances in perfume manufacturing sector.
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  Some of these saturated hydrocarbons are found in the tissues of plants and
animals as steroids.

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