Department of Chemistry

Faculty of Science
Cairo University

Basic Organic Chemistry 3

(CHEMISTRY OF BIFUNCTIONAL AND ALICYCLIC COMPOUNDS

Chem 244

2nd semester 2021-2022

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1. Course title and Code: Basic Organic Chemistry 3 (Chem 244)

2. Credit hours: 3h (2 Theoretical hours + 1 Practical hour)

3. Program(s) in which the course is offered: Bachelor of Science

4. Name of the faculty member responsible for the course:

Prof Dr. Nabila abdelshafy

5. Level/ Year at which this course is offered: 4th Level/ 2nd Year
6. Pre-requests for this course: Chem 241.
7. Co-requests for this course: No Co-requisites
8. Location: Department of Chemistry - Faculty of Science-Cairo University

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References
• A course note authorized by the department is available for the
students
• Note Title: “Bifunctional and Alicyclic compounds-Department of
Chemistry ‘’
Textbooks
I. Organic Chemistry, T.W.G Solomons 2005
II. Organic Chemistry, P.Y Bruice, 2004
III. Organic Chemistry, R.V Hoffman, 2004

Recommended books
I. Organic Chemistry, Bailey and Bailey, 1985
II. Organic Chemistry, Morrison and Boyd, 1992

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 Assessment
Assessment Credit (%)

Mid -Term Exam (MCQs) 10%

Practical Exam 30%

Final theory Exam 60%

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How to memorize
organic reactions ?

 Use reaction maps for

synthesis problems

(reaction maps allow you to see all

of the functional groups and the

reactions that occur to produce

them.

 You can use the reaction maps

to string together reactions to

get from one compound to the

final compound.)
Contents
Chapter 1 Dihydric Alcohols

Chapter 2 Hydroxy Aldehydes & Dicarbonyl compounds

Chapter 3 Halogeno carboxylic acid

Chapter 4 Hydroxy acids

Chapter 5 Keto acids

Chapter 6 Chemistry of Ethyl acetoacetate

Chapter 7 Dicarboxylic acid

Chapter 8 Amino acids and proteins

Chapter 9 Alicyclic compounds

 Organic chemistry is the study of the chemistry of carbon compounds

Classification of organic compounds

 Chapter 1

DIHYDRIC ALCOHOLS
 Definition
Dihydric alcohols are compounds containing two hydroxyl
groups.

They are classified as α, ,  …glycols according to the

relative positions of the two hydroxyl groups, e.g.,

α-glycols is the 1,2-Dihydric alcohols.

- glycols is the 1,3-Dihydric alcohols.

 Nomenclature
 The common names of the α-glycols are
derived from the corresponding alkenes, from
which they may be prepared by direct
hydroxylation.

CH2 CH2
H2C CH2
OH OH
Ethylene Ethylene glycol

CH3 CH CH2
CH3 CH CH2
OH OH
Propylene Propylene glycol
 According to the IUPAC system of nomenclature,
the class suffix is –diol and numbers are used to
indicate the positions of side-chains and the two
hydroxyl groups.

3 2 1 4 3 2 1

CH3 CH CH2 CH3 CH CH2 CH2

OH OH OH OH
Propane-1,2-diol Butane-1,3-diol
 Ethylene Glycol
 Viscous liquid, b.p. 197 oC
 Has a sweet taste
 Miscible with water

Methods of preparation:
1. By careful oxidation of ethylene with cold dilute
alkaline permanganate solution.
2. By the hydrolysis of Ethylene chlorohydrin.
Ethylene chlorohydrin, which is obtained from ethylene and
hypochlorous acid (HOCl), undergoes boiling with aqueous sodium
hydrogen carbonate (sodium bicarbonate) to yield ethylene glycol.

HOCl NaHCO3
H 2C CH2 H2C CH2 H 2C CH2
OH Cl OH OH
Ethylene
Ethylene chlorohydrin Ethylene glycol
3. By treating ethylene oxide with dilute hydrochloric acid.
reactions map

CH2 CH2
Ethylene
HOCl
[O]

CH2 CH2
H2C CH2 Conc HCl
OH Cl
O
KMnO4 Ethylene chlorohydrin
Alkaline
CH2 CH2
dil HCl
NaHCO3
OH OH

Ethylene glycol
 Chemical Reactions

The Chemical reactions of glycol are similar to those of

monohydric primary alcohols, except that the two hydroxyl
groups always react successively. Thus, it forms mono- and
di-sodium salts, mono- and di-esters, mono- and di-ethers,…

1. Ester Formation:
When glycol is treated with an organic acid in presence of an
acid catalyst, the mono- and the di-ester can be obtained.

CH2 OH CH3 COOH H+ CH2 OCOCH3 CH3 COOH H+ CH2 OCOCH3

CH2 OH - H2O CH2 OH - H2O CH2 OCOCH3

Glycol monoacetate Glycol diacetate
2. Dacron Formation:
When ethylene glycol is reacted with the dicarboxylic ester such as
dimethyl terephthalate, the poly-ester, Dacron (Terylene), is
obtained.

O O
H3CO C C OCH3 CH2 OH
+
CH2 OH
dimethyl terephthalate
-CH3OH Acid or base

O O O O
O C C OCH2CH2O -C C OCH2CH2O

poly ester (Dacron)

Dacron (polyester textile fiber)

3. Cyclic acetal and Cyclic Ketal:

Glycol condenses with aldehydes and ketones, in the presence

of acids, to yield the respective cyclic acetals or cyclic ketals.
 Dehydration reactions of
ethylene glycol

5. Dehydration using Conc. H2SO4 4. Dehydration using zinc chloride

or H3PO4
- 2 H 2O - H 2O

O
H2C CH2
CH3CHO
H2C CH2
O
Acetaldehyde
Dioxane

 Dehydration reaction is a chemical reaction that involves the loss of

water from the reacting molecule.
4. Dehydration using zinc chloride.

When glycol is heated with zinc chloride, it is

converted into acetaldehyde.

(Ethylene glycol to acetaldehyde)

5. Dehydration using concentrated sulphuric (H2SO4) or phosphoric acid
(H3PO4 ).

When glycol is heated with a little concentrated sulphuric or

phosphoric acid, dioxane is obtained.

(Ethylene glycol to Dioxane)

6. Oxidation reaction:

Glycol is oxidized with nitric acid to yield a series of

products which can be isolated.