IUPAC

NOMENCLATURE
 O
COOH
C O

Br CHO
OH

CH3
O
CH3 C C O C2H5
C
O N
Br
NO2
Introduction
Science of organic compounds is about 200 year old.

Chemical Substance

Organic Substances Inorganic Substances

These were obtained These were obtained from any
from living organism. other sources except living
Ex. Fat, Carbohydrates, organisms.
Protein etc. Ex. NaCl
Vital Force Theory (Vitalism) : By Berzelius in 1815

He suggested, a mysterious force (Vital force) in living organisms is

responsible for formation of organic compounds and organic compounds
cannot be synthesized in lab.

German scientist Wohler in 1828, synthesized an organic compound (Urea)

from inorganic compound in lab and Vitalism was disregarded.

NH4CNO NH2 C NH2
Rearrangement
O
Ammonium cyanate Urea
Kolbe synthesised acetic acid in 1845 and Berthelot synthesised methane in 1856.

NH 4 CNO ⎯⎯⎯⎯⎯
Rearrangement
→ NH 2 − C − NH 2
O
Features of carbon
(1) Tetravalency
Carbon has 4 electrons in outer shell so to complete its octet, carbon forms 4
covalent bonds. Carbon can form four bond in the following pattern

C C C C C C C C C
H

Li Be B C N O F

Na Mg Al Si P S Cl

Br

I
Covalent bond is of two types
(a) Sigma bond ()
The covalent bond formed between 2 atoms by the sharing of one electron
from each side.
(b) Pi () bond
Any other bond with  bond is  bond.
Single bond ( )   bond
Double bond ( )    bond
Triple bond ( )    bond
Illustration 1:
Calculate number of  and  bond in following compounds.
(A) Ethane (B) Ethene (C) Ethyne
(D) Benzene (E) Toluene (F) C2(CN)4
(2) Catenation
Ability of self linking to form chain is known as catenation. Carbon has got
the highest degree of catenation in the periodic table.

Very large number of organic compounds are known due to catenation

property of the carbon.
Condition for Catenation
1. Valency > 1

2. BDE should be high

(3) Homo atomic pi bond
(4) Carbon & not Silicon
(5) Reason for special features of carbon –
Reason for special features of carbon is position of the carbon in the
periodic table
Some Important terms
(i) Molecular formula
A formula that represents exact ratio of atoms in any compound is
known as molecular formula.
Ex. Molecular formula of acetic acid is C2H4O2 and that of glucose is
C6H12O6

(ii) Empirical formula

A formula that represents simplest ratio of atoms for a compound is
known as empirical formula.
Ex. empirical formula for both acetic acid and glucose is CH2O.
Illustration :
Consider the following
(I) CH3 – CH2 – OH
(II) CH3 – CH2 – CH2 – OH
(III) CH3 – CH2 – CH2 – CH2 – OH

(1) I & II are homologue (2) II & III are homologue

(3) I & III are homologue (4) All are correct

(iii) Homologous series
Homologous series may be defined as a series of similarly constituted
compounds in which the members possess the same functional group, have
similar chemical characteristics and have a regular gradation in their
physical properties. Two homologous differ by( – CH2 – ) unit.

Illustration :
Which one is not correct for a homologous series ?
(1) All members have a same general formula
(2) All members have same chemical properties
(3) All members have same physical properties
(4) All members have same functional group
Characteristics of homologous Series
Same functional group
Different molecular formula so different molecular weight
Same general formula but different empirical formula
Similar chemical properties
Different physical properties
Two consecutive homologues differ by one – CH2 – unit
Illustration :
Select the sets of homologues
(1) CH4, C2H6 & C3H8

(2) CH3 CH2 COOH & CH3 CH2 CH2 COOH

(3) CH2 OH CH2 CH2 OH

(4) OH CH2– OH
(5) OH & CH2– OH

O O
(6) CH3 C H & CH3 C CH3
There are three ways of representing of organic compounds
(i) Complete structural formula
Also Known as expanded from.
All the atoms and all the bonds are shown properly.
Lone pair of electrons on heteroatoms (O, N, S, halogens) may or may not
be shown.
(ii) Condensed structural formula
This is abbreviated from.
Hear the bonds are omitted.

(iii) Bond line formula

Carbon and hydrogen atoms bonded to carbon are not shown.
Carbon-carbon bonds are drawn in a zig-zag fashion.
Other hetero atoms (O, Cl, N, S etc.) are shown.
Example : n–Pantane

Expanded form Condensed form Bond line formula

Illustration :
Write expanded form of the following condensed forms
(a) CH3CH2COCH2CH3 (b) H3CCH CH(CH2)3CH3
 Degree of Carbon and Hydrogen
There are four types of carbon atoms
A primary (1°) carbon atom is bonded to one other carbon atom.
A secondary (2°) carbon atom is bonded to two other carbon atoms.
A tertiary (3°) carbon atom is bonded to three other carbon atoms.
A quaternary (4°) carbon atom is bonded to four other carbon atoms.
Degree of hydrogen is decided by the carbon to which hydrogen is attached
e.g. hydrogen atom bonded to primary carbon atom is primary hydrogen.
(i) n-butane (ii) Isobutane

CH3 CH2 CH2 CH3 CH3 CH CH3

CH3
(i) Isooctane (Commercial name)

Number of 1oC=
CH3 Number of 1oH=
Number of 2oC=
CH3 CH CH2 C CH3
Number of 2oH=
CH3 CH3 Number of 3oC=
Number of 3oH=
Number of 4oC=
(ii) Mesitylene

Number of 1oC=
Number of 2oC=
Number of 3oC=
Number of 1oH=
Number of 2oH=
Number of 3oH=

Note: Carbon of CH4 is known as super primary carbon or

simply primary carbon.
Classification of Organic Compounds Saturated Ex. CH4, C2H6, C4H10
Acyclic/Aliphatic Compounds
Organic Unsaturated Ex. H2C CH2, HC CH
Compounds Closed Chain/Cyclic Compounds

Homocyclic Compounds Heterocyclic Compounds

Alicyclic Compounds Aromatic Compounds

Alicyclic Compounds Aromatic compounds , ,

O N N O
, ,
Benzenoid Aromatic Compounds Non- Benzenoid Aromatic Compounds
NH2 OH O

, , ,
Aliphatic Compounds : Open chain compounds (branched or unbranched)
with no ring. These may be saturated or unsaturated.
Ex : CH4, C2H6, C4H10 H2C CH2, HC CH
Alicyclic Compounds : One or more carbon ring, saturated or unsaturated.
No aromatic character, may have aliphatic side chain

Ex :

Homocyclic Compounds : Cyclic compounds with same atoms

Ex : (cyclohexane)
Hetrocyclic Compounds : Ring with more than one type of atoms
Ex :
O
(oxane)

Aromatic Compounds : One or more cycle, follow Huckle's Rule. May be

benzenoid or nonbenzenoid.
Benzenoid Compounds : Aromatic compounds with atleast one benzene ring

Ex : NH2 OH

Nonbenzenoid Compounds : Aromatic compounds without benzene ring.

Ex : O
Quasi Aromatic Compounds :
Ionic in nature with counter ion and follow Huckle's Rule.

O– + –
+
Br– Na+
Hybridisation:
n (steric Number) Hybridistion
2 sp
3 sp2
4 sp3
n = n1 + n2
n1 = number of bond pairs ( bonds only)
n2 = number of lone pairs

C C C C
sp3 sp2 sp sp
Illustration :
H H H

(1) H C H (2) H C C H

H H H

H H
(3) H C C H (4) C C
H H
Illustration :
O
(1) CH3 - CH2 - O - CH3 (2) H H

N
(3) H H (4) CH3 - C C CH CH2
H
 Organic compounds and functional groups
Number of known organic compounds is very high so to make study easy these
compounds are placed into classes or families based on their structural
features. For example:
Alkane Alkene Alkyne
(CnH2n+2) (CnH2n) (CnH2n-2)
n = 2,3,4…..
n=1,2,3,4….. n=2,3,4…..
———
n = 1 : CH4 ———
n=2 : H 3C CH3 H2C CH2 HC CH
n=3 : H 3C CH2 CH3 H3C CH CH2 H3C C CH

Note : Alkane has no Functional group

IUPAC system of nomenclature
The IUPAC name of any organic compound may have five parts in the
following sequence.
2o Prefix + 1o Prefix + Word root + 1o Suffix + 2o Suffix
2o Prefix + 1o Prefix + Word root + 1o Suffix + 2o Suffix
Word root
It is the basic unit of the name. It denotes the number of carbon atoms present
in the parent chain (the longest possible continuous chain of carbon atoms
including maximum number of functional groups, multiple bonds and side
chains.
 Number of Number of Number of Word root
Word root
carbon Word root Carbon Carbon (Alk)
(Alk)
atoms in (Alk) atoms in atoms in
parent chain parent chain parent chain
1 Meth 9 Non 20 Icos
2 Eth 10 Dec 30 Triacont
3 Prop 11 Undec 40 Tetracont
4 But 12 Dodec 50 Pentacont
5 Pent 13 Tridec 60 Hexacont
6 Hex 14 Tetradec 70 Heptacont
7 Hept 15 Pentadec 80 Octacont
8 Oct 16 Hexadeca 100 Cent & Hect
Primary Suffix It represents saturation and unsaturation.
Type of carbon chain Primary suffix General Name
(a) Saturated -ane Alkane
(b) Unsaturated with one double bond -ene Alkene
(c) Unsaturated with one triple bond -yne Alkyne
If the parent carbon chain contains two, three or more double or triple bonds,
numerical prefix such as di (for two), tri (for three), tetra (for four) etc. are
added to the primary suffix. For example
Type of carbon chain Primary suffix General name
(a) Unsaturated with two double bonds diene Alkadiene
(b) Unsaturated with two triple bonds diyne Alkadiyne
(c) Both double and triple bonds enyne Alkenyne
Secondary Prefix It represents substituent or side chain.

Substituent Secondary
Substituent Group Secondary Prefix
Group Prefix
–F Fluoro –N2+ Diazo
–Cl Chloro –R Alkyl
–Br Bromo –C6H5 Phenyl
–I Iodo –OR Alkoxy
–NO2 Nitro –OPh Phenoxy
–NO Nitroso
 −𝐇
Alkyl Group : 𝐀𝐥𝐤𝐚𝐧𝐞 𝐂𝐧 𝐇𝟐𝐧+𝟐 𝐀𝐥𝐤𝐲𝐥 ( 𝐂𝐧 𝐇𝟐𝐧+𝟏 )
−[𝐇ሿ
𝐄𝐱. 𝐂𝐇𝟒 − 𝐂𝐇𝟑 (𝐌𝐞𝐭𝐡𝐲𝐥)

−[𝐇ሿ
𝐂𝐇𝟑 − 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐇𝟑 (𝐄𝐭𝐡𝐲𝐥)

CH3 CH2 CH3

(propane)
Cycloalkyl Groups

CH2 CH

–H
CH2 CH2 CH2 CH2
Cyclo propane Cyclo propyl

CH2 CH2 CH2 CH

–H

CH2 CH2 CH2 CH2

Cyclo butane Cyclo butyl
Alkenyl Groups
–H
Alkene (CnH2n) Alkenyl (CnH2n-1)

–[H]
Ex. 𝐇𝟐 𝐂 𝐂𝐇𝟐 − 𝐇𝐂 𝐂𝐇𝟐
Ethene Ethenyl

Alkynyl Groups
–H
Alkyne (CnH2n-2) Alkynyl (CnH2n-3)

–[H]
Ex. HC CH C CH
Ethyne Ethynyl
Phenyl Group

–H
Or C6H5 –
C6 H5 −

Phenyl (Ph)

Alkoxy Groups

-OCH3 : Methoxy
-OC2H5 : Ethoxy
-OPh : Phenoxy
Cyclo Alkoxy Groups

O : Cyclopropoxy

O : Cyclobutoxy

Methylene and Alkylidine Groups

CH2 CH–R

Methylene Akylidine (common name)

 Secondary suffix (2ºS)
It represents main functional group.
Functional group is given the least possible locant.
Functional group

Chain Terminating Non Chain Terminating

Functional groups with 1ºC Functional groups without
Ex. –COOH 1ºC or without Carbon
–COOR Ex. –OH
–COCl –SO3H
–CHO –NH2
–CN –CO– (ketone)
etc. –NC etc.
Priority Series of Functional Groups
Functional Functional group Name as side
Sr. Formula
2º Suffix
group chain
1 Carboxylic acid –COOH oic acid (carboxylic acid) Carboxy
2 Sulphonic acid –SO3H sulphonic acid Sulpho
3 Anhydride C O C oic anhydride ……
O O (carboxylic anhydride)

4 Ester C O R oate (carboxylate) alkoxy carbonyl

O or alkanoyl oxy
5 Acyl halide C X oyl halide (carbonyl halo carbonyl
halide)
O
6 Amide C NH2 amide (carboxamide) carbamoyl
O
7 Cyanide C H –nitrile (carbonitrile) cyano
8 Iso cyanide NC –isonitrile isocyano
9 Aldehyde C H -al (carbaldehyde) formyl / oxo
O
10 Ketone C one oxo
O
11 Alcohol OH –ol hydroxy
12 Thio alcohol SH – thiol mercapto
13 Amine N –amine amino
Priority for Selection of Wordroot Rule (X)
(1) Maximum principal functional group
(2) Maximum unsaturation(C C ,C C )
(3) Longest carbon chain
(4) Maximum substituents

Assigning of Locants Rule (Y)

(1) Lowest locant (2ºS > 1ºS > 2ºP)
(2) Alphabetical order
 Lowest set of Locant rule & Alphabetical Order
Single Entity  Lowest locant
Multiple Entities  Make set of locants and compare

Cl Cl Cl Cl Cl Cl Cl Cl

Br Br Cl Br Cl Br

( 2,3,6 ) ( 2,5,6 ) ( 2,3,5,6 ) ( 2,3,5,6 )

NOTE: The smallest sum of locants may lead to wrong results.

DPP–1

(1) 0

Pentane

(2) 0

But-1-ene

(3) 0

But-2-ene
(4)
0

But-1-yne

(5) 0 0 0 0

Pent-1,3-diene Pent-2,4-diene
Penta-1,3-diene
(6) 0
0
0
0

Pent-1-en-4-yne Pent-4-en-1-yne

(7) 0 0

Hex-1-en-3-yne
(8) 0
0

Pent-1-en-4-yne

(9) 0
0

0 0
0

0 0

Hepta-3,6-dien-1-yne Hepta-1,4-dien-6-yne
(10) 0
Prop-1-ene
Propene

0 0
0 0

(11)
0 0

But-1-en-3-yne But-3-en-1-yne
Butenyne
(12)

Cyclobutene Cyclobut-1-ene

(13)

Cyclohexene Cyclohex-1-ene

(14)

Cyclohex-1,3-diene Cyclohex-1,5-diene Cyclohex-1,2-diene

Cyclohexa-1,3-diene
(15)

Cyclohexa-1,4-diene Cyclohexa-1,3-diene

(16)

Cyclohexa-1,3,5-triene Benzene

( Hypothetical Benzene )
 Br Br

(1)
Cl Cl
2-Bromo-5-chloroheptane 6-Bromo-3-chloroheptane

Cl Br Cl Br
(2)
2-Bromo-6-chloroheptane 6-Bromo-2-chloroheptane
 Cl Cl

(3)
Br Br
5-Bromo-2-chloroheptane 3-Bromo-6-chloroheptane

Cl Cl Cl
(4)
2,4,6-Trichloroheptane
 Cl Cl
(5)
Br Br
5-Bromo-6-chlorohept-1-ene

Br Br

(6)
4-Bromonona-1,8-diene 6-Bromonona-1,8-diene
(7)
Br Br Br Br

3,7-Dibromonona-1,8-diene 3,7-Dibromonon-1,8-diene

Br
Cl Cl
(8) (9)
Cl

1-Bromo-3-chlorocyclo hexane 1,1-Dichlorocyclo hexane

 Cl Cl Cl Cl

(10)
Br Br
3-Bromo-1,1-dichlorocyclohexane 1-Bromo-3,3-dichlorocyclohexane
NOTE: (1) Numbers are separated from each other by commas(,).
(2) Numbers are separated from words by hyphens and there is
no break between name of substituents and word root.
Cl Cl
Br Br
(12)

I I
2-bromo-1-chloro-3-iodocyclohexane
 Br Br Br

(13)

3-Bromocyclohexene

Br Br

(14)

Cl Cl
3-Bromo-6-chlorocyclohexene
 Br Br
(15)
Cl Cl
4-Bromo-5-chlorocyclohexene 5-Bromo-4-chlorocyclohexene

Cl Cl
Br Br
(16)

Br Br
4,6-Dibromo-3-chlorocyclohexene 3,5-Dibromo-6-chlorocyclohexene
 Br Br Br
Cl Cl Cl
(17)

Br Br Br
3,6-Dibromo-1-chlorocyclohexene
 Home Work

(1) (2)

2,5-Dimethylheptane 2,6-Dimethylheptane

(3) (4)

2,5-Dimethylheptane 2,4,6-Trimethylheptane
(5) (6)

5,6-Dimethylhept-1-ene 3,6-Dimethylnon-1,8-diene

(8)
(7)

3,7-Dimethylnona-1,8-diene 1,3-Dimethylcyclohexane
(9) (10)

1,1-Dimethylcyclohexane 1,3,5-Trimethylcyclohexane

(11) (12)

1,1,3-Trimethylcyclohexane 1,2,3-Trimethylcyclohexane
(13) (14)

3-Methylcyclohexene 3,6-Dimethylcyclohexene

(15) (16)

4,5-Dimethylcyclohexene 3,4,6-Trimethylcyclohexene
(17) (18)

1,3,6-Trimethylcyclohexene 3,6-Diethyl-2-methyloctane

(19) (20)

Methylcyclopropane Ethylcyclopropane
(21) (22)

Propylcyclopropane 2-Cyclopropylbutane

(23) (24)

1-Cyclopropyl-2-methyl-propane 1-Methyl-2-propylcyclopropane
 (26)
(25)

2-Cyclopropyl-3-methylbutane 1,1-Diethylcyclopropane
 CH3 CH2– CH3
(1) (2)

Methylcyclopropane Ethylcyclopropane

H3C CH2 CH3 CH2 CH CH2 CH2 CH3

CH CH3
(3) (4)

2-Cyclopropylbutane 3-Cyclopentylhexane
 Br
(5) CH2 CH2 CH3 (6) CH2 CH CH3

Propylcyclopropane 2-Bromo-1-cyclopropylpropane

(7) CH2 CH2 CH3 (8) CH3 CH2 CH CH2 CH2 CH3

Br
1-Bromo-2-propylcyclopropane 1'-Ethyl butylcyclohexane
Br Br
Cyclic + Acyclic System

(1) Follow the rule (X)

(2) If all features same  cyclic part would be the main chain
(8) (9)

1-Ethylcyclohexene 3,3-Dimethylcyclohexene

(10)

Cyclohexylethene
(11) CH2 (12)

Dicyclopropylmethane 1,2-Dicyclopropylethane

(13) (14) C

1-Cyclopentyl-2-cyclopropylethane Tetracyclopropylmethane
NOTE: If more than one alicyclic ring is attached to a single chain then the
compound is named as a derivative of alkane and the ring are treated as a
substituent group.
(15) (16)

Methylbenzene (Toluene) Ethylbenzene

(17) (18)

Propylbenzene Cyclohexylbenzene
(19) CH (20) Br

Triphenylmethane 2-Bromo-1-phenylpropane

Br

(21)

2'-Bromobutyl cyclopentane
Alphabetisation
In constructing the name, substituents are cited in alphabetical order, e.g. an
ethyl group proceeds a methyl group.
Numerical prefixes (di-, tri-tetra- etc.) are ignored unless there is a complex
side chain.
Prefixes such as sec, tert- (or their abbereviations) are ignored.
The prefixes iso, neo and cyclo are included (note they are used without
hyphens and are part of the substituent name)
For systems named with complex substituents, the following additional
guideline applies.
In alphabetising complex substituents, any terms used in the brackets are
included.
For example (1,1-dimethylethyl) is alphabetised as “d”
This is because the term in brackets is the name of whole complex substituent
and not several individual substituents.

4-(1,1-dimethylethyl)-5-ethylnonane
not
5-ethyl-4-(1,1-dimethylethyl)nonane
Alcohol Alcohol

1º R CH2 OH OH

2º R CH OH
Non chain terminating
R

3º R C OH 2ºS ol
R
Alcohol Non chain terminating

OH

(1) OH (2)

Hexane-1-ol Pentan-2-ol
Hexan-1-ol
OH
(3) (4)
OH OH
Pentan-2-ol Butan-2,3-diol
Butane-2,3-diol
 OH OH
(5) Butane-1-2,3-triol
OH

(6) CH2 CH CH2

Propane-1,2,3-triol
OH OH OH
(Glycerol)

OH

(7) OH Cyclopentane-1,2-diol
 OH OH
Br Br
(8)
Br Br

5,6-Dibromocyclohex-2-enol

OH OH
OH OH
(9)

Br Br
5-Bromocyclohex-3-ene-1,2-diol
 OH Cl OH

(10) (11)

Br
Phenol 3-Bromo-5-chlorophenol

OH OH

(12) (13)
CH CH2 3-Butylpent-4-en-2-ol
3-Ethenylphenol
 Carboxylic Acid
O Br
C O H (1)
COOH

4-Bromoheptane-1-oic acid

Chain terminating
Br

oic acid COOH

2º S
carboxylic acid 4-Bromoheptanoic acid
 COOH COOH

(2)
Br Br
3-Bromo-2-methylheptanoic acid

COOH
(3)
2-Propylpentanoic acid

HOOC COOH HOOC COOH

(4)

2-Ethyl-4-methylpentanedioic acid
 COOH COOH (OMS GAP)
(5) (6) CH2
COOH COOH
Ethanedioic acid Propanedioic acid
(Oxalic Acid) (Malonic Acid)
CH2 COOH CH2 COOH
(7) (8) CH2
CH2 COOH CH2 COOH
Butanedioic acid Pentanedioic acid
(Succinic Acid) (Glutaric Acid)

CH2 CH2 COOH CH2 CH2 COOH

(9) (10) CH2
CH2 CH2 COOH CH2 CH2 COOH
Hexanedioic acid Heptanedioic acid
(Adipic Acid) (Pimelic Acid)
(11) CH3 CH COOH (12) CH2 COOH

2-Cyclopropylpropanoic acid Cycloprophylethanoic acid

CH2 COOH
COOH

(13) (14)

Cyclopropanecarboxylic acid
Phenyclethanoic acid
 COOH COOH

(15) (16)

Cyclohexanecarboxylic acid Benzenecarboxylic acid

COOH

(17)
COOH

Benzene-1,3-dicarboxylic acid
 HOOC COOH HOOC COOH

(18)
COOH COOH
Cyclohexane-1,1,3-tricarboxylic acid

COOH COOH

CH2 CH CH2 CH2 CH CH2

(19)
COOH COOH COOH COOH
Propane-1,2,3-tricarboxylic acid
 HOOC COOH COOH HOOC COOH COOH
(20)
COOH COOH
Nonane-2,3,6,8-tetracarboxylic acid

(21) HOOC COOH COOH HOOC COOH COOH

CH2 CH2
COOH COOH
7-Carboxymethylnonane-2,4,8-tetracarboxylic acid
(21) HC COOH

HC COOH
Butenedioic acid
Q Select the correct statements
(A) SO3 is anhydride of H2SO4 (B) Na2O is anhydride of NaOH

(C) N2O5 is anhydride of HNO3 (D) (CH3CO)2 is anhydride of CH3COOH

 Acid anhydride
O O
C O C OR (CO)2O

Chain terminating

oic anhydride
2º S
carboxylic anhydride
 (1)
O
O
CH3 C O H
CH3 C
O
O CH3 C
CH3 C O H O
OR
Ethanoic acid
(Acetic acid) CH3 C O C CH3

O O

Ethanoic anhydride
(Acetic anhydride)
 (2)
O
O
CH3 CH2 C O H
CH3 CH2 C
O
O CH3 CH2 C
CH3 CH2 C O H O
OR
Propanoic acid
CH3 CH2 C O C CH2 CH3

O O

Propanoic anhydride
(3) H C O C H

O O

Methanoic anhydride

H C OH HO C H

O O

Methanoic acid
 (4)
O
O
CH3 C O H
Propanoic acid CH3 CH2 C
O
O CH3 C
CH3 C O H O
OR
Ethanoic acid
CH3 C O C CH2 CH3

O O

Ethanoicpropanoic anhydride
(5) C O C

O O
Cyclopropanecarboxylic anhydride

C O H + H O C

O O

Cyclopropanecarboxylic acid
(6) C O C

O O
Cyclobutanecarboxyliccyclopropanecarboxylic anhydride

C O H + H O C

O O

Cyclopropanecarboxylic acid Cyclobutanecarboxylic acid

(7) C O C

O O
Benzenecarboxylic anhydride

C O H + H O C

O O

Benzenecarboxylic acid
(8) CH3 CH2 CH3 C O C CH2 CH3

O O
Butanoicpropanoic anhydride

CH3 CH2 CH3 C OH + HO C CH2 CH3

O O
Butanoic acid propanoic acid
 O
O
C
OH
(9) O
OH
C
O
O

Cyclohexane-1,2-dicarboxylic acid Cyclohexane-1,2-dicarboxylic anhydride

 O
O
C
OH
(10) O
OH
C
O
O
Benzene-1,2-dicarboxylic acid Benzene-1,2-dicarboxylic anhydride
 O
O
(11) C
OH
O
OH
C
O
O
Butanedioic acid Butanedioic anhydride
 O O
(12) OH
O
OH

O O

Octa-3,4-dienoic acid Octa-3,4-dienoic anhydride

 Cyanide

CN

Chain Terminating

Nitrile
2º S
Carbonitrile
(1) CN (2) NC CN
Pentanenitrile Pentane-1,5-dinitrile
Pentanedinitrile

CH2 CN CN

(3) (4)
2-Cyclopropylethanenitrile Cyclopropanecarbonitrile
Cyclopropylethanenitrile
 CN CN

(5) (6)

Cyclohexanecarbonitrile Benzenecarbonitrile

(7) CH2 CH CH2

CN CN CN
Propane-1,2,3-tricarbonitrile
 Aldehyde
O
C H

Chain Terminating

al
2º S
Carbaldehyde
 CHO
(1) (2) CHO
CHO
Butanal Hexanedial

CHO
CHO
(3) (4)

Cyclopropanecarbaldehyde Benzenecarbaldehyde
 CHO CH2 CHO

(5) CH2 CH CH2

(6)
CHO CHO
2-Cyclopropylethanal
Propane-1,2,3-tricarbaldehyde
Cyclopropylethanal

OHC CHO CHO

(7) (8)
CHO
CHO Ethanedial
Cyclohexane-1,1,3-tricarbaldehyde
 Acid halide
O
O O
C X
C Cl C Br
oylchloride oylbromide
carbonylchloride carbonylbromide
Chain Terminating
O O

Oyl halide C I C F
2º S oyliodide oylflouride
Carbonyl halide carbonyliodide carbonylflouride
 O
Cl Cl
(1) C (2) C C
Cl
O O
Butanoylchloride Pentandioylchloride

O
O
C Cl
C Cl

(3) (4)

Cyclopropanecarbonylchloride Benzenecarbonylchloride
 O O

Cl C C Cl

Cyclohexane-1,3,5-tricarbonyl chloride
(5)
C Cl
O

COCl

(6) Cyclohexane-1,3-dicarbonyl chloride

COCl
Amide Chain Terminating Amide
O
H
1º C N Chain Terminating
H

O
H amide
2º C N 2º S
R
carboxamide
O
R
3º C N
R'
 O
H2N NH2
C (2) C C
(1)
NH2 O O
Butanamide Pentanediamide

O
O
(4) C
(3) C
N
NH
N-methylbutanamide N-ethyl-N-methylbutanamide
 O O

(5) CH3 CH CH2 C NH2 (6) CH3 CH CH C NH2

Br CH3 Br
2-Brombutanamide 2-Bromo-3-methylbutanamide
 H3C CH3 O

(7) CH3 C C C NH2

2,3-Dimethyl-3-cyclopropyl-2-phenylbutanamide

(8) CH3 CH CH C NH2

CH3 CH2

CH3
2-Ethyl-3-methylbutanamide
(9) H2N NH2
C C
C NH2
O O
O
Propane-1,2,3-tricarboxamide

(10) C NH2

Cyclopropancarboxamide
 O
C NH2

(11)

Benzenecarboxamide

O
C
(12) N
Br

4–Bromo–N–cyclohexyl–N–phenylhexanamide
 O

(13) C
N

N–cyclopentyl–N–cyclopropylcyclohexanecarboxamide
O
(14) H C NH2
Methanamide

(15) CH3 C NH2

Ethanamide