Lecture 22-24

*Important memorize*

Double and triple bonds in organic compounds produce?

variety of structures with di ering properties

Number of ways to arrange carbon and other atoms?

1- Branched chains

2- Ring structures

3- Linear chains

Di erences Between Organic and Inorganic Compounds:

 Families of Organic Compounds:

Hydrocarbons Substitute
hydrocarbons
Properties:

1- only carbon and hydrogen

one or more hydrogen atoms is replaced
2- Nonpolar by another atom or group of atoms

3- Not soluble in water

4- Are soluble in nonpolar organic solvent

Toluene Pentane

5- chains or rings of carbon atoms with su cient

hydrogen atoms
6- low mp and bp
7- Less dense than water
8- As length increases, (mp, bp, density) increases
9- Van Der Waals attraction
10- can be oxidised (by burning) through combustion

11- react with a halogen( Cl , Br) through halogenation reaction

Families :

Aliphatic
Aromatic

Alkanes Cycloalkanes Alkenes Alkynes

Ethane Ethene Ethyne

 Formulas Used in Organic Chemistry:

Molecular Structural Condensed Line

formula formula formula formula

•kinds & numbers •each atom & bond

•sequential order •carbon atoms
at line intersect

The Tetrahedral Carbon Atom:

.‫ بسبب انها تكون اربع روابط وجميعها فردية‬١٠٩.٥ ‫ وتكون الزاوية‬tetrahedral ‫ تعطي شكل‬alkanes ‫*دائما‬
ً

Lewis dot structure Tetrahedral Tetrahedral with Tetrahedral Ball and stick
dashes and wedges stick drawing

Di erences between Alkane, Alkyl and isomers:

Alkanes Isomers
Alkyl •Many carbon compounds exist in
the form of isomers
•Melting and boiling points increase
•Alkane with one hydrogen
with increasing molecular weight •compounds with the same molecular
atom removed
formula but di erent structures
•The majority of the reaction of
alkanes are combustion
•named by replacing the -ane Such as: Butane and Methylpropane

of the alkane name with -yl

•Isomers with the same molecular formula
Complete Incomplete and have di erent physical properties

produces Carbon produces Carbon

dioxide and water monoxide and water •Melting and boiling points decrease
with increasing branching
 Cycloalkanes

have two less Naming :

Structures: Isomers in
hydrogens than
cycloalkane:
the corresponding
chain alkane
-are stereoisomers whose
Add cyclo- before the name Structural: substituents di er in atom
of the corresponding alkane arrangement
Place substituents in
Condensed:
alphabetical order

use the lowest possible Line: (Cis) : Two groups on the

set of numbers for substituents same side

(Trans) : Two groups on

the the opposite side

Halogenation

reaction results from

Products of this ONLY occurs in the Converts unreactive
replacement of one can occur at all
reaction are: presence of heat alkanes into
group for another positions to give
and/or light (UV) starting material
a mixture of
• Alkyl halide or
monosubstituted
haloalkane
products
• Hydrogen halide

What is Halogenated hydrocarbons? hydrocarbons containing two or more halogen atoms.

What are they used for? 1-used in medicine as anesthetics, such as:
chloroethane, chloromethane

2- as insecticides, such as:

DDT, chlordane, and lindane.
Lecture 25-27
Alkenes and alkynes can be converted to alkanes:

Add catalyst (H2)

Add catalyst (2H2)

Who has the highest melting and boiling points ? 1- Alkyne ; because it needs
more energy to break down.
2-Alkene
3-Alkane

Alkenes are abundant in nature

2 double bonds 3 double bonds

Myrcene

Geraniol

Farnesol
D- Limonene
 1- addition
Alkene reactions: 2- oxidation

Addition reaction to alkene:

Hydrogenation: Halogenation: Hydrohalogenation: Hydration:

It is a reduction reaction
-addition of hydrogen -addition of water
-addition of H2 -addition of halogen halide (HCl , HBr) -need strong acid
-need catalyst (pt, pd, ni) (Br2, Cl2) -no catalyst catalyst (H+)
-both hydrogen is in the -no catalyst -produce alkyl halide -produce alcohol
same side (cis) -produce alkyl dihalide *unsymmetrical; *unsymmetrical;
-heat/pressure may be -result in a colourless immediately follow immediately follow
required solution markovnikov rule markovnikov rule
-produce alkane

Addition reaction to alkyne:

Hydrogenation: Halogenation: Hydrohalogenation: Hydration:

-addition of 2H2 -addition of halogen -addition of (HBr,HCl) -addition of water

-if catalyst (pt, pd, ni) is -no catalyst -no catalyst -has an initial product
used : product is alkane -product trans-alkene -product is alkene (Enol) which isn’t stable
-when lindlar’s catalyst -if added (2halogen) -if added (2HBr, 2HCl) -need strong acid
is used : product is cis- product will be alkane. product will be alkane. catalyst
alkene , it cannot give -OH will break down to
product alkane. be stable
- nal product is either
aldehyde or ketone
Lecture 28-30
Important to memorize *
 Benzene:

The real benzene molecule: based on overlapping of P orbitals

perpendicular to
the plane of the
carbon ring

How to de ne an Aromaticity ?

Which hydrocarbons cause cancer ? Polynuclear aromatic hydrocarbons (PAH)

For example:

How to di erentiate between benzene

being substitute or parent group?
 Benzene reactions: substitution reactions*

1- Halogenation: Br2 , Cl2 will substitute one H

Catalyst : Fe , FeBr3 , FeCl3

2- Nitration : NO2 will substitute one H But how?

Make HNO3 react with catalyst H2SO4
-water is product

3- Sulfonation: SO3H will substitute one H But how?

Make SO3 react with catalyst H2SO4
-water is product

4- Alkylation: Alkyl will substitute one H

And the halogen will go with the
hydrogen that left the ring

Catalyst : AlCl3

5- Alcylation:
Acyl group will substitute one H
And the halogen will go with the hydrogen that
left the ring
Catalyst : AlCl3

Oxidation: Reduction:

Catalyst: Zn(Hg) Zinc Amalgam

Lecture 31-33
 Isomers:

Stereoisomers:
Structural
isomer:

It has in uence on the chemical properties

Conformers:
Con gurations
isomers:

Enantiomers: Diastereomers:

-it doesn’t have a mirror image

-it doesn’t have handednes
-it has a mirror image -superimposable
-it has handednes -Achira
-nonsuperimposable -symmetri
-chira -has a plane of symmetr
-Asymmetri -one has same con guration ,
-chiral Carbon is called: other has opposite.
1-stereognic cente
2-stereocente
3-has tetrahedral geometr
-they have same & different properties

Same physical properties 1-different biological- physiological

properties.

2-different optical activity & rotation.

Both enantiomers have the same specific
rotation but in opposite directions.
 Fisher rule: Can I know how many
stereoisomers of any
molecular? 🤔

Sure! Just use this equation !

Meso compounds:

It must have more the It has a plane of It is Achiral Mirror and image Different m.p
one chiral center symmetry! molecule! are superimposable!
Lecture 34-36
 Alcohol general formula: R-OH

Functional group: Hydroxyl group

Physical properties

Polarity B.p
Very polar High boiling
point
Because of hydrogen bond
between water and alcohol Because of hydrogen bond
between different alcohol

Alcohol classi cation:

Medically Important Alcohols:

Methanol Ethanol Propanol Ethanediol

Colorless and odorless liqui Colorless and odorless liqui Colorless and odorless liqui -Antifreeze

-Solvent -Solvent -Industrial solvent

-sweet taste👅 ,
-In alcoholic beverages -rubbing alcohol but poisonous
-Toxic!!!! Cause blindnes
-Used as fuel -Toxic
-Drived from fermentation of -Lower freezing
-Astringent point
carbohydrates
-Disinfectant
-Raises boiling point
 Alcohol reactions:

Preparation Oxidation
Dehydration It is a Dehydrogenation reaction.

is a type of elimination reaction

Hydrogenation 1- Primary alcohol ——-> aldehyde

Hydration
Addition and reduction reaction.
•primary alcohol———> carboxylic acid

2- Secondary alcohol ——-> ketone

3- tertiary alcohol.. no oxidation!!!

Major product
Minor product
 Phenol: Ar -OH

Differences
Physical Similarities
with alcohol:
properties: with alcohol:
•alcohol + phenol can be converted
-pola to alkoxide RO- (conjugated
-water soluble •functional group (OH)
•have pleasant scent base) by adding 2k or NaH
-component of fragrance
-phenyl cation is unstable; •phenol can be converted to
breaking C-OH is dif cult phenoxide ion by adding
NaOH or KOH

Ether: R-O-R

Physical Reactions:
properties:
-pola
-low boiling point; because there
is no H bon Preparation of Preparation of Williamson
symmetrical ethers unsymmetrical ether synthesis
-iner
-volatil
-do not react with reducing
agent, and base
-easily oxidized in ai
-Flammable
-anesthetics; halogenated ethe
-Accumulate in the lipid
material of nerve cell

Thiol: R- SH

Physical properties: thiol-disul de :

Thiols, as many other sulfur containing when oxidation it becomes disul de bridge in
compounds can have nauseating aroma protein structure

Onions and garli striped skunk

Lecture 37- 39
 1- carboxylic aci ‫ﺗﺮﺗﯿﺐ اﻟﻤﺮﻛﺒﺎت ﺣﺴﺐ اﻻﻛﺜﺮ اﻟﻰ اﻻﻗﻞ‬
2- alcohol :‫درﺟﺔ ﻟﻠﻐﻠﯿﺎن‬
3- keton
4-aldehyde
5- este
6-ethe
7- amin
8- alkane

Carbonyl group:

Physical properties: Uses:

•Pola
•in fragrance
•can’t form hydrogen bond •in medicine
between each other; low b. •in agricultural chemical
•in food chemicals
•water bond hydrogen bond
with them; high solubilit

•exist mainly in keto form

How to distinguish between aldehyde and ketone?

Tollen’s Tes Benedict’s Tes

 Aldehyde:

Uses:
Reactions:
•Methanal (formaldehyde) - gas
used in aqueous solution as
formali Preparation: Oxidation: Reduction: Addition:
-product is
• Ethanal (acetaldehyde) - primary alcohol
causing hangover symptoms -using
hydrogenatio
-or using reducing
reagents:

LiAlH4 NaBH4

Ketone:

Reactions:
Uses: Can it be oxidized?!
• Propanone (Acetone) :
1-Miscible with wate Addition
2– Flammabl Preparation: Reduction:
3-very versaile solvents
-product is
(also butanone ) secondary alcohol
-using hydrogenatio
-or using reducing
reagents
Lecture 40-44
 Carboxylic Acids :

Physical properties: Names: Important uses:

•Veryyy polar!! why? Because -citric acid in citrus fruit

of two functional group
-lactic acid is produced by
•low molar mass: bacteria
-water soluble
-sour tast -tartaric acid is used in
-unpleasant aroma baking powde

•high molar mass -malic acid in 🍏

-high boiling point
-in fatty aci -fatty acid in animal&plant
source
•weak acid with dissociation
less than 5%

Reactions:

Preparation: Dissolving in water: Neutralization

reaction:

Carboxylic acid salt uses:

•soup -> sodium stearat
•preservative

•Anti-funga
•control pH
 Ester:

Ester with pleasant aroma: •Banana 🍌 oil :

•pineapple 🍍 aroma:

•raspberry 🫐 aroma:

Ester Reactions:

Preparation: Hydrolysis ( hydration) Reduction:

Acid hydrolysis: Base hydrolysis:

Acid chloride reactions:

Preparation: Reaction with Nucleophiles:

1- Acid chloride + H2O -> carboxylic aci

2-Acid chloride +Alcohol -> Este

3- Acid chloride + 2NH3 -> amid

 Acid Anhydrides :

Aspirin synthesis:
Preparation: Substitution with Nucleophiles:

1- Acid Anhydride + H2O ->

2 carboxylic acid

2-Acid Anhydride +Alcohol -> Ester +

carboxylic aci

3- Acid Anhydride + NH3 -> Amide+

carboxylic acid

Amide:

Structure: Physical properties: Preparation:

•solid; high b.

•weak aci

•water solubl

•strong bond between N-H one

amide to C=O another amide.

Amine:

Structure: Physical properties: Reactions:

•weak base

•tertiary amines don’t form

hydrogen point; boils lower than 1, 2

•all amines up to 6carbon are water

soluble.