Organic chemistry

Faculty of Allied Medical Sciences

(MGOC-101)

Supervision:Prof.Dr.Shehata El-Sewedy

Dr. Fatma Ahmed

Outcomes By the end of this lecture, the

students will be able to1-Recognize physical properties for alcohol

2-Known nomenclature of aliphatic and aromaticalcohol

3 -learn preparation of aliphatic and aromatic alcohol

4 -known reaction of aliphatic and aromatic alcohol

5-Differentiate between aliphatic and aromatic alcohol

6 -Understand the order of acidity

Alcohol

as function group of alcoholROH

OH

R O

H

H O

R

Hydrogen bond

Physical propertiesAlcohol soluble in polar solvent (H2O)Alcohol have high boiling point due to have intermolecular hydrogen bond

So alcohol its boiling point higher than corresponding alkane, ether which have the same number of carbon

ROH> R-H> R-O-RAlcohol Alkane ether

Alcohol

R-CH2OH CHOH

R

R COH

R

R

R

1 Primary alcohol 2 secandary alcohol 3 Primary alcoholAlcohol

Mono hydric Dihydric Trihydric R-OH

ex: CH3OH Methyl alcohol

CH2OH

CH2OH

Ethylene glycol

CH2OH

CHOH

CH2OH

Glycerol

As number of OH group increase hydrogen bond increase, boiling point increase & viscosity increase.

Nomenclature1-Common nameAlkyl name+alcohol

CH3OH

Methyl alcohol

CH3CH

CH3

OH

iso-Propyl alcohol

CH3CHCH2CH3

OH

sec-Butyl alcohol

CH3C

CH3

OH

CH3

3 -Butyl alcohol

2-IUPAC1-Select the long continuous chain have OH as parent name (alkane

-e+ol alkanol)2-Number from side near to OH group to give lowest number (position+alkanol)3-Substitution its position& name write4-Priority in numbering of groups-COOH>-CHO>-CO->-OH>alkene>alkyne>R

EX:

CH3CHCH2CHCHCH3

OH

CH3

CH3

1 2 3 4 5 6

4,5-Dimethyl-2-hexanol

H2C CH

CH2

OH

2-Propen-1-ol

CH3CH2C C CH2CH2OH123456

3-Hexyn-1-ol

Preparation of alcohol1-Reduction of carbonyl group

C O

R

R

H2/ Ptor LiAlH4or NaBH4

CH OH

R

R

EX:

CH3CH

O

Acetaldehyde

H2/ PtCH3CH2

OH

ethanol

CH3CCH3

ONaBH4 CH3CHCH3

OH

Acetone iso-propyl alcohol

2-By Grignard reagent

R-X Mg RMgX Alkyl magnesium halide (Grignard reagent)

RMgX + C

O

x y

x=y=H,C2H5,CH3,......

C

OMgX

x yR

HOHC

OH

x yR

Alcohol

+ MgXOH

EX:

CH3CH2MgBr + C

O

HH

Ethyl magnesium bromide formaldehyde

CH3CH2CH2OMgBrHOH

CH3CH2CH2OH

n-Propyl alcohol

1 alcohol

CH3CH2MgBr + C

O

CH3H

Ethyl magnesium bromide acetaldehyde

CH3CH2CHOMgBrHOH

CH3CH2CHOH

sec-Butyl alcohol

2 alcohol

CH3CH3

CH3CH2MgBr + C

O

CH3H3C

Ethyl magnesium bromide Acetone

CH3CH2COMgBrHOH

CH3CH2COH

3 -pentyl alcohol

3 alcohol

CH3CH3

CH3 CH3

N.Bformaldehyde 1 alcohol

Any aldehyde except formaldehyde

2 alcohol

Acetone 3 alcohol

Grignard reagent +

Grignard reagent +

Grignard reagent +

3-Oxymercyrcation-Demercurcation of alkene

C C

B

A C

D

+ Hg

OAc

OAc

HOH

AcOHC CB

A C

D

OH HgOAcoxymercuration

NaBH4demercuration

C CB

A C

D

OH H

Alcohol

EX:

CH3CH CH2Propene

Hg

OAc

OAc

HOH-AcOH

CH3CHCH2

OH HgOAc

NaBH4 CH3CHCH3

OH

iso-Propyl alcohol

Reaction of alcohol1-Oxidation of alcohol

CH3CH2OHK2Cr2O7

H2SO4CH3CH

O

Acetaldehyde

CH3CHCH3

OH

K2Cr2O7

H2SO4

CH3CCH3

O

Acetone

CH3CCH3

OH

K2Cr2O7

H2SO4

CH3

No reaction

1 alcohol

2 alcohol

3 alcohol

2-Esterification

R C

O

OH + HOR/ HR C

O

OR/

Ester

+ H2O

EX:

H3C C

O

OH +H

H3C C

O

OCH2CH3

ethyl acetate

+ H2OHOCH2CH3

Acetic acid ethanol

OH OH OH

OH

OH

OH

2,4-Dinitrophenol Salicylic acid Catechol Resorcinol

NO2

NO2

COOH1

23

456

OH OH

Br

OH

CH3

OH

CH3

Phenol m-Bromophenol o-Cresol m-Cresol

Nomenclature

Preparation of phenolsFrom halobenzene

Cl ONa OH

Chlorobenzene Sod.phenoxide Phenol

NaOH H

Reactions of phenolsEther formation

OH ONa OR

Phenol Sod.phenoxide

NaOH R + NaX

Ether

X

OH ONa OCH3

Phenol Sod.phenoxide

NaOH H3C + NaCl

Anisol

Cl

Ex.

The order of acidity

RCOOH ˃ Ar-OH ˃ HOH ˃ R-OH

Phenol is more acidic than alcohols because:-OH O O

Phenol

O

OO

Phenoxide ion (phenolate)stabilized by resonance

R-O-H R O + H

Alcohol Alkoxide ion unstable

Quiz time

Complete:NaOH + HOHPhenol ...............

OCH3

NaOH + NaClPhenol ............... ................

CH3CH

O

H2/ Pt.................

CH3CCH3

OH

K2Cr2O7

H2SO4

CH3

.................

CH3CH CH2

Hg

OAc

OAc

HOH

NaBH4.................. ...................

Arrange for the order of acidity:

R-OH - RCOOH - HOH - Ar-OH Convert:

Acetone 3 -pentyl alcohol

Phenol Anisol

PhenolChlorobenzene

Student Question

CH3CHCH2CHCHCH3

OH

CH3

CH3

H2C CH

CH2

OH

CH3CH2C C CH2CH2OH

.............................. ........................... ...............................................

Write the nomenclature for the following compounds

iso-Propyl alcohol sec-Butyl alcohol 3 -Butyl alcohol

Write the chemical formula for the following compounds?

Assignments(1)Group A and Group B

Samar Mostafa- Omnia Mosaad -Esraa Kamel- Reem khaled -

Shrouk Essam

Applications of glycerol

Ahmad Rada Kamel – Ahmad Mohamad Abd El Salam- Ahmad El Said- Ahmad Alaa

Oxidation of Alcohols

Sara Lotfy- Shimaa Saied – Esraa Sameh-Ahmad Shadra-Ibrahim El-Habet- Ibrahim El Said

Uses of Amines

Aya Ibrahim – Shreen Hassan – Mohamad Ahmad Torky- Mohamad Montaser- Doaa Sabri

Effect of Acetophenone on health

Someya Mostafa – Maram Ahmad – Esraa Mahmoud

Nucleophilic reaction

Youssef AboBakr – Mina Melad – Omar Gamal Kamal

Electrophilic reaction

Assignments(2)Group A and Group B

Hanan Ahmad Zaid -Alfa Magdi - Alaa Kamal Anani – Asmaa Mohamad El-Awadi- Sara Ali Abd El-Latif- Alaa Emad El Din – Eisha Youssef

Applications of acetone

Hagar Saeed – Shrouk Abd El-Aziz – Mona Ashraf Ramadan – Nahed Atia –Mai Mahmoud-Haidy Mahmoud – Walaa Ebada

Uses of Anisole

Khaled Eid- Sameh Raafat- Bishoy Shanoda-Sobhy Sabry-Ahmad Saeed Shehata-Abd El Rahman Abd El Aziz-Ahmad Zian-Mohamad Waheed

Applications of Salicylic acid in industry

Aya Ibrahim – Shreen Hassan – Mohamad Ahmad Torky- Mohamad Montaser- Doaa Sabri-Asmaa Gamal-Mahmoud Ezzat-Shady –Rewan Mohamad-Ahmad-Taha Mohamad Nasri - Eisha Ali

Effect of Formaldehyde on health

Assignments(3)Group A and Group B

Hend Nazmy – Heba Waheed – Hagar Eman Gamal - Adel

Intermolecular Hydrogen bond

Mostafa Ahmad Shata – Abd El Rahman Ali-Mohamad Magdi- Motasem Abd El-Aal

Acidity of Alcohols

Mohamad Mahmoud Awad-Marwa Ahmad-Sara Emad –Mariam Hamdy

Applications of Benzoic acid

Marina Maged-Nourhan Emad-Engy Roshdy-Madonna Micheal-JosianIsaq-Merna Farag Allah-Christin Magdi-Verona Romani-Makarious Maher-Mena Malak

Organic compounds in food

Assignments(4)Group A and Group B

Eman Gamal- Mona Ashraf Kamal- Fahd Abd El Salam-Mohamad Montaser-Wasal Mohamad

Effect of Phenol on health

Kholod El-Said – Riham Hassan – Esraa Hafez-Asmaa Basha –Asmaa Mohamad Hassan-Dina Nassem

Cancer

Ibrahim Abd El Aatti-John Micheal-Bishoy Sadeek

Uses of Toluene

Mariam Thrwat- Kyrillos Rafaat – Mina Kabeel-Fadi Abd El Salam

InfraRed spectroscopy

Recommended textbooks:1-Raymond Chang. Chemistry: An introduction to organic chemistry. 10th ed. 2009 2008

2-Zumdehl. Organic Chemistry; study guide and solution manual. 2008