Lecture Notes 2

Functional groups in
Organic Chemistry
CHEM120
 Functional groups
• Groups of atoms that are responsible for chemical behaviour of
the molecule.
• Similar functional groups have similar characteristics.
Family Name Functional Examples Name Name ending
groups
     
 
Alkane ethane
Carbon-carbon -ane
single bond

   
   
Alkene ethene -ene

   
 
Alkyne ethyne -yne
 
   
 
Arene benzene  none

   
 
Alcohol ethanol  -ol
2
Family Name Functional Examples Name Name ending
groups
     
 
Amine Ethylamine
1⁰ 2⁰ -amine
3⁰
   
   
Nitrile ethanenitrile -nitrile

Carbonyl groups
Not in isolation
Always in conjunction with other functional
groups.
Carbon double bonded to oxygen
Depends on atoms attached to carbonyl
CARBONYL
carbon.
Family Name Functional Examples Name Name ending
groups
     
 
Aldehyde ethanal
-al

   
   
ketone propanone -one

   
 
Carboxylic acid Ethanoic acid -oic acid
 
   
 
Amide ethanamide  -amide

   
 
esters Methyl- -oate
ethanoate 
 Identify the functional groups present in the
following compounds

Banana oil

100 % nylon 5
 Organic Nomenclature /naming
• Three parts to a compound name:
Prefix-Parent-Suffix

Prefix : Tells what groups (substituents) are

attached to the chain.
Parent : Tells how many carbons are in the
longest continuous chain.
Suffix : Tells what type of compound it is.
(Alkanes, alkenes, alkynes, alcohol, aldehyde, etc.)

IUPAC: International Union of Pure and Applied

Chemistry
 To Name a Compound…
IUPAC: International Union of Pure and Applied
Chemistry

IUPAC systematic naming

1. Find the longest carbon chain in the molecule

2. Number the chain from the end nearest the first

substituent encountered.

Substituents : group(s) of atoms not part of the longest

chain
 Preparation of Aldehyde and Ketones
Ozonolysis Reaction.
NB!! carbonyl group takes the lowest position number possible.

• Reaction of alkenes with ozone (O3)

propanal Butan-2-one

• Aldehydes Ketones
Carbonyl not specified position specified
Preparation of acyl halides
Ozonolysis Reaction.
 Practice 5
i. When (E)-3-chloro-hex-3-ene is reacted with ozone in dimethyl
sulfide, it gives two carbonyl compounds. Draw the structures of
products and give their IUPAC names.

ii. Which products will be formed during the ozonolysis of 3,5-

dibromo-4-methyl-oct-3-ene?
 Exercise K
i. When (E)-5-bromo-hept-3-ene is reacted with ozone in dimethyl
sulfide, it gives two aldehydes. Draw the structures of aldehydes
and give their IUPAC names.

ii. When compound A, with molecular formula C5H8 is treated with

1 mole of H2, in the presence of Li in NH2 it gives compound B.

When B reacts with ozone it gives ethanal and compound C.
Identify compounds A, B and C. Also specify the configuration of
compound B.
 Oxidation of alcohols.
Preparation of Ketones and Aldehydes

1° or 2° alcohols are converted to ketones and aldehydes

Two types of oxidising agents

 Strong oxidizing (CrO3 or K2Cr2O7 in H2SO4(aq)), oxidizes

1° alcohols to carboxylic acid and 2° alcohols to ketones

 Weak oxidizing agent (PCC), oxidizes

1° alcohols to aldehydes and 2° alcohols to ketones

 Exercise L
Give the products of the following reactions
a) Reaction of propanol with acidified potassium dichromate solution
b) Reaction of 3-cyanopent-2-ol with PCC
c) Reaction of 4-methylpent-3-ol with acidified potassium dichromate
solution
d) Reaction of butanol with PCC
e) Reaction of 2-methylbutan-2-ol with acidified potassium dichromate
solution
 Exercise M
i. When compound A, with molecular formula C6H10 is treated with

1 mole of H2, in the presence of Lindlar catalyst it gives

compound B. When B reacts with ozone it gives compound C
and D. When compound D is reacted with PCC, it gives ethanol.
Identify compounds A, B, C and D. Also specify the configuration
of compound B
 Reduction of carbonyl compounds.
Preparation of alcohols
• Ketones and aldehydes can be converted to alcohols using a
reducing agent (NaBH4)

Sodium borohydride
 Exercise M

Give the products of the following reactions

a) Reaction of 2-butanone with sodium borohydride

b) Reaction of 3-cyanopentanal with NaBH4

c) Reaction of 4-methylpent-3-one with a reducing agent

d) Reaction of 2-methylbutan-2-ol with acidified potassium
dichromate solution
 Carboxylic Acids and its derivatives
Carboxylic acid (-oic acid)

3-Chloro-4-fluoropentanoic acid

Amides (-amide)

3-Chloro-4-fluoropentamide

N-methyl-3-Chloro-4-fluoropentamide
 Carboxylic Acids and its derivatives
Carboxylic esters (-oate)

Formed from carboxylic acids and alcohols process called

esterification reaction.

Butan-1-ol Propanoic acid Butyl propanoate

Ethyl butanoate Methyl propionate

 Exercise N
• Write a correct IUPAC name or line structure of the following
molecules.
a) N-propyl-5-Iodopentanamide
b) N,N-dimethyl-2-ethyl-5-methylheptanamide
c) 4-cyano-3-oxopentanoic acid
d) Methyl butanoate
e) Butyl 4-bromo-3-methyl-2-oxohexanoate
f) butanenitrile
 Multifunctional Compounds
Compounds with more than one functional groups!

IUPAC rules for functional group priority When the following functional groups
are substituents.
Highest
Functional Group Name -OH (hydroxy) and -NH2
-COOH Carboxylic acid (amino), -CN (cyano).
-COOR Ester
-CONH2 Amide
-RCN Nitrile
-CHO Aldehyde
RCOR Ketone
-OH Alcohol
-NH2 Amine

CnH2n-2 Alkyne

CnH2n Alkene
Lowest
CH Alkane
 Exercise O
Name the following compounds When a nitrile is a substituent = cyano

……………………………………..……………
……………………………………..………………

……………………………………..………………
……………………………………..………………
 Exercise P
Name the following compounds

…………………………………….. ……………………………………..………………..
………………………..

……………………………………..………………………. ……………………………………..……………………….
Acetylide ion formation.
 Exercise Q
• When compound A, with molecular formula C3H4 reacts with

compound B (C3H7Br) in the presence of NaNH2 it give compound C

(C6H8). Compound C reacts with 1 mole H2 in the presence of Pd/C to

generate compound D. A treatment of compound D with ozone
produces butanal and compound E. A reaction of compound E with

NaBH4 gives compound F. When compound F reacts with

3-cyanobutanoic acid in the presence of an acid it gives
ethyl 3-cyanobutanoate.
• Identify compounds A-F