MASTERING ORGANIC CHEMISTRY By-- S.K.

SINHA 1

The IUPAC Systematic Approach to Nomenclature

• Identify Root:-Find the parent hydrocarbon. This is based on the longest continuous carbon chain. If
there are chains of equivalent length, then select the one with the most branch points as the parent.

• Number the chain:-Number the atoms in the parent chain, beginning at the end nearer the first
branch point. If there is branching an equal distance from both ends, then consider the next branch
point.
• Identify the substituents:- Identify and number the substituents. Remember there must be as many
numbers as there as substitutents.
• Writing the name:- Write out the name as a single word, using hyphens to separate the different
prefixes and commas to separate the numbers. If two or more different substitutents are present, cite
them in alphabetical order. With identical substituents, use the prefix di-, tri-, tetra- etc. as required.
Ignore these prefixes when alphabetising.
• If a substituent has subranching (ie. its complex) then reapply the first 4 steps as if it were a
compound. Numbering must begin at the point of attachment. Now set this substituent in
parentheses.
Naming the parent chain: Here is a list of the root names for the hydrocarbon chains
C1 = meth- C2 = eth- C3 = prop- C4 = but- C5 = pent- C6 = hex- C7 = hept- C8 =
oct- C9 = non- C10 = dec- C11 = undec- C12 = dodec- C18 = octadec- C20 = icos-
IUPAC Rules for Naming Organic Molecules
To name a compound using the IUPAC system, follow the steps shown (if applicable) in the following
order.

Step 1 Determine the principle functional group in the compound. When a compound contains more than
one group in Table 1, the principle group is that which has the highest precedence. This group will be
cited as a suffix; all other groups are cited as prefixes.

Functional Suffix if Highest Prefix if Lower

Group Precedence Prededence
-(C)aOOH -oic acid -
-COOH -carboxylic acid carboxy-
-SO2OH -sulfonic acid sulfo-
-C(O)OC(O)- -oic anhydride -
-(C)OOR alkyl -oate alkoxy-oxo-
-COOR alkyl carboxylate -
-(C)OX -oyl halide halo-oxo-
-COX -carbonyl halide halocarbonyl-
-(C)ONH2 -amide amino-oxo-
-CONH2 -carboxamide aminocarbonyl-
-(C)≡N -nitrile -
-C≡N -carbonitrile cyano-
-(C)HO -al oxo-
-CHO -carbaldehyde formyl-
>(C)=O -one oxo-
-OH -ol hydroxy-
-SH -thiol sulfanyl-
-NH2 -azane (-amine) azanyl- (-amino)
>NH -azane (-imine) azanylidene-
>C=C< -ene *
-C≡C- -yne **
-X, -R, -OR - halo-, alky-l, alkoxy-
-Ar, -NO2 - aryl-, nitro-
-NO, -N3 - nitroso-, azido-
=N2, -SR - diazo-, (R)-sulfanyl-
a
(C) designates a carbon atom included in the parent hydrocarbon (part of the longest chain or ring.
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2 MASTERING ORGANIC CHEMISTRY By-- S.K.SINHA
* and ** These are always used as a suffix. If a higher priority group is present in the molecule the suffix
is changed to –en– or –yn– and is followed by the suffix of the higher priority group.
Step 2
Determine the parent hydrocarbon (principle chain or ring system system):
(a) If the principle group occurs in a chain, the principle chain is selected as
(i) the chain containing the functional group of the highest seniority as the parent.
OH

2-(propan-1-yl)pentan-1-ol

(ii) If more than one such choice is possible, select the chain with the maximum number of
multiple bonds.

2-(hexan-1-yl)buta-1,3-diene
(iii) If (i) and (ii) together are not definitive, then choose the longest chain.
(iv) If two chains of the same length are possible, choose the one with the maximum number of
substituent groups.
O H

2-(butan-1-yl)-4-methylhexanal
The parent chain here contains six carbon atoms.
(b) If the principle functional group occurs in a cyclic system, that cyclic system forms the parent.

OH

2-(octan-1-yl)cyclohexanol 2-(hexan-1-yl)cyclopentene

Step 3 Name the parent structure of and the principle group(s). Give the parent name the same name as
if it were an alkane, but replace –ane with the suffix characteristic of the functional group of the highest
priority (Table 1). Note: Multiple unsaturation in hydrocarbons is indicated by the numerical prefixes di-,
tri-, etc. In such cases, however, the ending –ane of the parent alkane is replaced with –adiene, –atriene,
etc. leaving the “a” in the root alkane name whenever the first letter of the suffix is a consonant to make
the name easier to pronounce. Thus we get alkadienes, alkatrienes, alkadiynes, etc.
Step 4 Complete the number system.
(a) Number the carbon atoms consecutively from the end of the chain nearer the functional group of the
highest priority.
1

2 3 5
6
4,5-dimethylhexan-3-one
4

O
(b) If the same number for the functional group of highest priority is obtained in both directions, the
correct IUPAC name is the one that contains the lowest substituent numbers.
1

6
2 4 2,4-dimethylhex-3-ene
3 5
The substituent numbers are 2 and 4. If we numbered from the other end, the substituent numbers
would have been 3 and 5. 2+4 is a lower numbering system than 3+5.
(c) If the first substituents occur at an equal didtance from each end of the chain, number the end
nearer a second substituent. If still the same, continue until the first point of difference.
(d) If numbering for either end gives the same set of numbers, number from the end with the substituent
that comes
6 first in alphabetical order.

2 1
5
4
3 2-chloro-5-methylhex-3-ene
Cl

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 MASTERING ORGANIC CHEMISTRY By-- S.K.SINHA 3
(e) In monosubstituted cycloalkanes and benzene derivatives. The carbon to which the substituent is
bonded is always number 1. If there is only one substituent, the locant number “1” is omitted.
However, the number one is required in polysubstituted compounds.
CH3 NO 2

OH
Cl I Br

Cyclopentanol 1-chloro-2-methylcyclohexane 2-bromo-4-iodo-1-nitrobenzene

(f) In polysubstituted cyclic compounds, the starting point and the direction of numbering are chosen to
give the lowest numbering system. The starting point is chosen according to the following factors:
(i) The principle functional group named as the suffix is always given the lowest possible number.
Because certain cyclic systems have fixed numbering systems, it is not always possible to place a
substituent on carbon number 1.
6 4
8 1
HO NO 2 CH3
5 Br OH
1 5 3
7 2
6 2
2 4 N 3
6
1
3 5
IUPAC: 3-nitrobenzen-1-ol 3-methylazabenzene 7-bromonaphthalene-2-ol 4
(3-nitrophenol accepted) (3-methylpyridine accepted ) (7-bromo-2-naphthol accepted)
Note: When one heteroatom is present in the ring the number 1 is assigned to that atom. If more than
one is present then we use the number 1 on the O, S, or N in that order of priority.
3 4 3 4
4
5 N N3
2 5 S 2 5 6 2
O O N
1
1 1
IUPAC: oxole(Furan accepted) 1,2-oxathiolane 1,3,5-triazine
(ii) Lowest numbering for multiple bonds in cyclic compounds.
4 2
Cl CH3 OH
5 3 3 1

6 2 4 6
CH3
1 5
5-chloro-3-methylcyclohexene 6-methylcyclohex-3-en-1-ol
Note: In naming cycloalkenes, the double bond is located between C1 and C2, and the “1” is
usually omitted in the name. The ring is numbered clockwise or counterclockwise to give the first
substituent the lower number. However, when functional group with a higher priority than an
alkene is present, the carbon bonded to the higher priority group becomes C1 and then multiple
bonds are considered for lowest possible numbering.
(iii) Lowest numbering for first substituent (or first point of difference).
Cl CH3 CH2CH2CH3
3 5 6 1
4 2
5 6 1 4 2
3
OH Cl CH3

4-chloro-2-methylcyclohexan-1-ol 4-chloro-2-methyl-1-(propan-1-yl)cyclohexane
(iv) If the same numbers will result from numbering in either direction, give the lowest number for
the substituent that is cited first in the name.
4 Br
CH3
3
2 3
4 2
CH2CH3 5 1
1 6
Cl O

2-ethyl-3-methylnaphthalene 3-bromo-5-chlorocyclohexanone
Step 5 Name alkyl groups, halides, and other substituents and determine their position on the chain by
the numbering system established by step 4.
Step 6 Assign the stereochemistry to chiral carbon atoms (stereocenters) and the double bond(s):

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4 MASTERING ORGANIC CHEMISTRY By-- S.K.SINHA
(a) Disubstituted alkenes may be named in two ways: (i) using terms cis- and trans- or (ii) using terms
(E) or (Z). Note: Use of (E) and (Z) stereocenters is preferred. However, the cis-trans terms are
accepted.

(E)-pent-2-ene or trans-pent-2-ene (Z)-hex-3-ene or cis-hex-3-ene

(b) Tri-
6
and tetra- substituted alkenes may only be named using the (E-Z) system.
1

5 3 (E)-2,3,5-trimethylhex-3-ene
4 2

(c) Disubstituted cycloalkanes may be named using the terms cis-trans or (R-S).
CH3
cis-1-chloro-4-methylcyclohexane
Cl
(R-S) system not applicable here
H CH3
trans-3-methylcyclopentanol
HO (1R,3R)-3-methylcyclopentanol
H
(d) Chiral carbon atoms are assigned (R) or (S) configuration.

(S)-5-methylhexan-3-ol
H OH

HO H
COO
(2S,3R)-2-amino-3-hydroxybutanoic acid
H3N H
common name: threonine

(e) When both (R-S) and (E-Z) stereodescriptors are present, they are placed in parentheses followed
by a hyphen; each stereodescriptor is immediately preceded by its associated number and they are
arranged in numerical
H OH
order.
Cl CH3

(3S,4E)-6-methylhept-4-en-3-ol (2Z,4E,6R)-6-chloro-6-methylocta-2,4-diene
Step 7 Compounds with multiple bonds and triple bonds have the following suffixes: –adiene, –
adiyne, –atriene, –atetraene, and so on. Specify the location of each multiple bond by a locant number
placed between the “a” and diene, diyne, triene, etc.

(E)-2-ethylhexa-1,4-diene
previously: (E)-2-ethyl-1,4-hexadiene
Step 8 Compounds with both double and triple bonds are called enynes. Start the numbering of enynes
from the end nearest the first multiple bond, regardless of type. When a double bond is the same distance
from one end as a triple bond from the other end, assign the double bond the lower
7
8 number.
6 4 2 1
2 4 6
7 5 3 1 3 5

(E)-hept-5-en-1-yne (E)-oct-2-en-6-yne
Step 9 Write the complete name of the compound as a single word with the correct locant numbers for
all substituents, which are listed in alphabetical order. The prefixes di, tri, tetra, etc. do not alter the
alphabetical ordering of the substituents. The stereochemistry is indicated by placing the appropriate
prefix within parentheses followed by a hyphen in front of the name.
Cl
(E)-5-chloro-3-methyl-3-en-2-one
1
6 2
5 3
4
O
O

4-ethyl-2,5-dimethylhexanal

(a) The numbers indicating locations of substituents are separated by commas.

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 MASTERING ORGANIC CHEMISTRY By-- S.K.SINHA 5
(b) The letters and numbers are joined by hyphens.
(c) When naming esters, no hyphen is placed between the name of the alkyl group derived from the
alcohol
O
and the name of the acid from which the ester was derived.
methyl butanoate
O

Step 10 A complex substituent is named by applying the above steps just as if the substituent were a
compound itself. We begin numbering the sidechain at the point of attachment to the parent hydrocarbon
giving the carbon at the point of attachment the locant of C1. We then give this substituent the suffix –yl.
We put this name in parentheses and in front of the parentheses we place the locant number on the
parent hydrocarbon.
SH
OH
Br
2-(bromomethyl)benzenethiol 4
3 2
1
2
OH
3-(4-methylcyclohexyl)propane-1,2-diol
3 1

When a complex sidechain contains a chain that is attached to the parent hydrocarbon at a position other
than at the end of the chain, the carbon of attachment is still numbered as C1 and the other part of the
chain is named as a substituent group to that chain.
2
1 3
4
1 3
2 4

(1-ethylbutyl)benzene 1-(2-ethyl-1-methylbutyl)-2-methylcyclohexane
Note: An alternate method of numbering the sidechain is to find the longest chain and begin numbering
at the end closest to its attachment to the parent hydrocarbon. The –yl ending is added to the chain
parent name and the position of the attachment is placed before the –yl ending.
1
2
3
4
5
1-(3-ethylpentan-2-yl)-2-methylcyclohexane

The table below shows some examples of IUPAC names for commonly known compounds. The IUPAC
system allows the trivial names of these compounds to be retained as official IUPAC names and, for
some, to be used in naming substituted compounds such as 4-bromobenzoic acid. The IUPAC systematic
name for this compound would be 4-bromobenzenecarboxylic acid.
OH

N
IUPAC:
Trivial (retained) azabenzene 1,2-dehydrobenzene benzenol
pyridine benzyne phenol

NH2 NH2
NH2

CH3

IUPAC: phenylazane 2-methylphenylazane naphthalene-2-ylazane

benzenamine 2-methylbenzenamine naphthalene-2-amine
Trivial (retained) aniline ortho-toluidine 2-naphthylamine
O
O O

OH
OCH3
IUPAC:
Trivial (retained)
benzenecarboxylic acid methyl 1-phenylpropan-1-one
benzoic acid benzenecarboxylate propiophenone
methyl benzoate

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6 MASTERING ORGANIC CHEMISTRY By-- S.K.SINHA

CH3 O CH CH2

C
H3C CH3
IUPAC:
Trivial (retained) methylbenzene propan-2-one (ethenyl)benzene
toluene styrene
acetone
Many other trivial names are also retained but can only be used for the unsubstituted compound. For
example, the names butanoic acid (systematic) and butyric acid (trivial retained) are both approved by the
IUPAC. However, BrCH2CH2CH2COOH must be named systematically as 4-bromobutanoic acid and
cannot be named as 4-bromobutyric acid.

Hantzsch-Widman System
Element Valence Prefix Element Valence Prefix
Silicon IV Sila Oxygen II Oxa
Sulfur II Thia Tin IV Stanna
Selenium II Selena Tellurium II Tellura
Boron III Bora Nitrogen III Aza Phosphorus III Phospha
Stems for the Hantzsch-Widman System
The stem for six-membered rings depends on the least preferred heteroatom in the ring i.e., the
heteroatom whose name directIy precedes the stem.

To determine the proper stem for six-membered rings, select the set below that contains the least
preferred heteroatom before consulting the table.

Ring size Unsaturated Saturated Ring size Unsaturated Saturated

3 irene irane 7 epine epane
4 ete etane 8 ocine ocane
5 ole olane 9 onine onane

Common nomenclature -
Common nomenclature is an older system of naming organic compounds. Instead of using the prefixes
for the carbon skeleton above, another system is used. The pattern can be seen below.
Number of Prefix as in new Common name for Common name for Common name for
carbons system alkanol aldehyde acid
1 Meth - Formaldehyde Formic acid
2 Eth - Acetaldehyde Acetic acid
3 Prop - Propionaldehyde Propionic acid
4 But - Butyraldehyde Butyric acid
5 Pent Amyl alcohol Valeraldehyde Valeric acid
6 Hex - Caproaldehyde Caproic acid
7 Hept Enanthyl alcohol Enanthaldehyde Enanthoic acid
8 Oct Capryl alcohol Caprylaldehyde Caprylic acid
9 Non - Pelargonaldehyde Pelargonic acid
10 Dec Capric alcohol Capraldehyde Capric acid

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 SINHA IIT CHEMISTRY 8

A. Common Parent Ring Systems

8 1 8 9 1
7 2 7 2
or
6 3 6 3
5 4 5 10 4
benzene
naphthalene anthracene

B. Monosubstituted Benzenes
1. Most substituents keep their designation, followed by the word “benzene”:
Cl NO2 CH2CH3

chlorobenzene nitrobenzene ethylbenzene

2. Some common substituents change the root name of the ring. IUPAC accepts these as root
E IT A
names, listed here in decreasing priority:
H I H

Y
COOH SO3H CHO OH NH2 OCH3 CH3
N

TR
SI

IS
benzoic benzene- benzaldehyde phenol aniline anisole toluene
acid sulfonic acid
M

C. Disubstituted Benzenes
1. Designation of substitution—only three possibilities:
X X X
C

Y
Y
common: ortho- meta- para-
IUPAC: 1,2- 1,3- 1,4-

2. Naming disubstituted benzenes—Priorities determine root name and substituents

Br COOH
HO

NH2 OCH3
Br 3-aminobenzoic acid CHO CH3
1,4-dibromobenzene 2-methoxybenzaldehyde 3-methylphenol

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 SINHA IIT CHEMISTRY 9

D. Polysubstituted Benzenes
CH3 COOCH2CH3
Cl O2N NO2

HN Cl OH
CH3 NO2 NH2
3,4-dichloro-N-methylaniline 2,4,6-trinitrotoluene ethyl 4-amino-3-hydroxybenzoate
(TNT)
E. Aromatic Ketones
A special group of aromatic compounds are ketones where the carbonyl is attached to at least one
benzene ring. Such compounds are named as “phenones”, the prefix depending on the size and
nature of the group on the other side of the carbonyl. These are the common examples:
O O
C CH3 C CH2CH3

acetophenone propiophenone
E IT A
O O
H I H

Y
C CH2CH2CH3 C
N

TR
SI

butyrophenone benzophenone
IS
M
C

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 SINHA IIT CHEMISTRY 14

• Characteristics of organic compounds

Homologous series
Compounds with the same functional group, differing only in the number of CH2 units in their
skeleton are said to be in the same homologous series. They are part of the same family of
compounds with similar reactions and characteristics that differ only in the number of carbon
atoms that make up the chain. Members of a series will have formula that are linked by a general
formula. For example, all alkanes have the general formula CnH2n+2.

All organic compounds have six identifying characteristics each.

1. Molecular formula - showing the actual number of atoms of each element in that compound.
E.g. C2H4O2 for ethanoic acid, meaning there are two carbon atoms, four hydrogen atoms and
two oxygen atoms.

2. Empirical formula - the simplest whole number ratio of the atoms of each element in that
compound. E.g. CH2O for ethanoic acid, meaning there is a ratio of 1:2:1 of C:H:O atoms.

3. Structural formula - showing how those atoms are arranged. E.g. CH3CO2H for ethanoic acid,
E IT A
meaning three hydrogen atoms are attached to one carbon atom, which in turn is attached to
H I H
another carbon atom, which in turn has two oxygen atoms attached to it, one of which has a

Y
hydrogen atom attached to it.
N

TR
4. Graphical formula - showing how these atoms are arranged in space and the bonds between
SI

them. Lines represent covalent bonds (shared pairs of electrons) between atoms. E.g. for
ethanoic acid, where = represents a double covalent bond and – represents a single covalent
IS
bond.
M

H O H

H C C

H O
C

5. Skeletal formula – showing an abbreviated form of the carbon chain, with each line segment
understood to have a carbon atom at each end. These structures may or may not show terminal
(end of chain) carbons. E.g. for ethanoic acid

O O

OH Or H3C OH

6. Name - based upon an accepted system for naming compounds (IUPAC nomenclature). E.g.
CH3CO2H, is called ethanoic acid.

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 SINHA IIT CHEMISTRY 18

ALKANES
1. Name the following compounds

i) CH3C(CH3)2CH2CH3

ii) CH3CH2C(C2H5)2CH2CH2CH3
iii) CH3CH(CH3)CH2CH(CH3)CH3
iv) CH3CH2CH(CH3)CH(C2H5)CH2C(CH3)2CH3
2. Draw graphical formula for the following compounds

i) 2-methylpropane
ii) 3-methylheptane
E IT A
iii) 2,3-dimethylbutane
iv) 2,2,6-trimethyloctane
H I H

Y
v) 1,3-diethylcyclobutane
N

TR
3. Name the following compounds
ALKENES & ALKYNES
SI

i) CH3CH2CH=CH2
IS
ii) CH3C≡CCH3
iii) CH3CH2CH(CH3)C≡CCH3
M

iv) CH3C≡CCH(CH3)2
v) CH2=CHCH=CH2

4. Draw graphical formula for the following compounds

i) 2,3-dimethylbut-2-ene
C

ii) 4-methylhex-1-yne
iii) 3,4-diethylhex-2-ene
iv) 4-ethylcyclohex-1-ene
v) 4-ethylcyclohex-1-ene
HALOGEN COMPOUNDS

5. Name the following compounds

i) CH3CH2CH2CH2CH2I
Br
O

ii)
iii) (CH3)2CHBr

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 SINHA IIT CHEMISTRY 19

6. Draw graphical formula for the following compounds

i) 2-iodo-2-methylpentane
ii) 1-chloro-1-bromoethane
iii) triiodomethane
iv) 1-bromo-3-chloro-4-methylhexane
ALCOHOLS
7. Name the following compounds
i) CH3CH2CH(OH)CH2CH3
ii) CH3C(CH3)(OH)CH2CH3
iii) CH3CH(OH)CHBrCH3
8. Draw graphical formula for the following compounds
i) pentan-2-ol
ii) 3-methylhexan-1-ol
iii) cyclohexane-1,3-diol
ALDEHYDES & KETONES
9. Name the following compounds

i) CH3CH2CH2CHO
ii) CH3CH(CH3)COCH3
iii) CH3CH(CH3)CHO
E IT A
iv) CH3CH(CH3)COCH3
10. Draw graphical formula for the following compounds
H I H

Y
i) cyclohexanone
ii) 3-methylbutanal
N

TR
iii) 2,2-dimethylpropanal
SI

iv) 3-chlorobutan-2-one
CARBOXYLIC ACIDS & DERIVATIVES
IS

11. Name the following compounds

M

i) CH3CH2CO2H
ii) CH3CH2CH(OH)CH2COOH
iii) (CH3)3CCO2H
H3C Cl
C

iv) H3C O

12. Draw graphical formula for the following compounds

i) pentanoic acid
ii) 3-aminopropanoic acid
iii) butenedioic acid
iv) chloroethanoic acid
v) methylpropanoate

NITROGEN COMPOUNDS
13. Name the following compounds
i) CH3CH2CN
ii) (C2H5)3N
14. Draw graphical formula for the following compounds
i) 2-methylbutanonitrile
ii) 3-aminopentane

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Name the following compounds according to IUPAC rules:

1 2 3

Br

4 5 6

Cl
7 8 9

Br

Cl

10 11 12 Cl
Br
Answer Key: Alkane Nomenclature

1. 2,3-dimethyl-5-propylnonane
2. 4-bromo-2,2,7,8-tetramethylnonane
3. 3-ethyl-2,4,6,7-tetramethylnonane
4. 2,3-dimethyl-6-[1,2-dimethylpropyl]decane
5. 2,7-dimethyl-5-[1,1-dimethylpropyl]nonane
6. 1-isopropyl-4-methyl-2-propylcyclohexane
7. 1-chloro-1-cyclopentyl-4,4-dimethylheptane
8. 7-bromo—3-cyclopropyl-6-ethyl-2,6-dimethylnonane
9. 3-chloro-1,1-dimethylcyclopentane
10. cis-1-isopropyl-3-methylcyclohexane
11. 2-bromo-4-sec-butyl-1,7-dimethylcyclodecane
12. 1-chloro-2-isopropyl-1,5-dimethylcyclooctane
Aldehydes and Ketones: Nomenclature Problems:
Name the following according to IUPAC rules.

O O
1. 2.

H H

O
3. 4. O

OH
O
5. O 6.
HO H
O
O

O
7. 8. OH O

O
9. 10.
O

O
11. 12.

OH
13. 14. Br
O O

O H
Aldehydes and Ketones: Nomenclature Answers

1. 4-ethyl-5-methyloctanal

2. 3-n-butyloctanal (or 3-butyloctanal)

3. 6-isopropyl-7-decen-5-one

4. 6-hydroxy-5-methyl-2-hexanone

5. 2,7-octanedione

6. 9-hydroxy-6-oxononanal

7. 3-pentylcyclohexanone

8. 7-hydroxy-3-octenal

9. 4-[2,2-dimethylpropyl]cyclohexanone

10. 1,3-cyclohexanedione

11. 3-[3-hydroxypentyl]cyclohexanone

12. 1-cyclopentyl-2-hexanone

13. 2-[3-oxobutyl]cyclopentanone

14. 2-[1-bromopropyl]hexanal
.
:

1.1 Give the IUPAC name of each of the compounds shown.

a) CH3 CH2 CH2 CH2 CH3 b) CHCl3 c) CH3 CH2 CHCH 3

|
OH

d) CH3 CH2 CHCH 2 CH3 e) (CH3 )2 CHCHBrCH 2 CH3

|
CH3

f) (C2 H5 )2 CH(CH 2 )2 CH3 g) CH3 CH3

| |
CH3 CH2 CHCH 2 CHCHCH 3
|
CH2 CH2 CH3

h) CH3 CBr2 CH2 CCl3 i) CH3 CH2 CHCH 2 CH2 CH3

|
CH2 OH

j) (CH3 )2 CHCH 2 CH2 C=CH 2 k) CH3

| |
CH3 CH3 CH2 C-C≡C-CH(CH 3 )2
|
CH3

l) CH3 CH2 Br m) CH3 CH2 H

C C C C
Br H CH3 CH2 H

1.2 Draw the structure of each of the compounds named below.

a) 2,2-dimethylbutane b) 3,3-dimethyl-1-butanol

c) 4-ethyl-2,2-dimethylhexane d) 1,2-dibromo-2-methylpropane

e) 4-methyl-2-pentyne f) cis-1-bromo-2-pentene
2.1 Give the IUPAC name of each of the compounds shown.
CH3
a) b) (CH3 )2 CH c) d) Cl Cl
OH

2.2 Draw the structure of each of the compounds named.

a) 1,3-dimethylcyclobutane b) 4-neopentylcyclohexanol c) 4-isopropylcyclohexene

3.1 Give the name of each of the compounds shown.

CH3

a) b) c) Cl d)

CH3
3.2 Draw the structure of each of these compounds.
a) bicyclo[2.2.0]hexane
b) 2-isopropylbicyclo[1.1.0]butane
c) 1,5-diethylbicyclo[3.3.0]octane

4.1 Give the common name of each of the compounds shown.

a) CH3 CH2 OH b) CH3 CH2 CH2 Cl c) (CH3 )3 C-CH2 OH d) FC(CH3 )3

4.2 Draw the structure of each of the compounds named.

a) methyl iodide b) isobutyl alcohol c) isopropyl alcohol d) sec-butyl bromide

5.1 Give the common name of each of the following compounds.

OH Br
a) OH b) c)

5.2 Draw the structures of the following compounds.

a) cyclopropyl chloride b) cyclohexyl iodide

6. Draw the structures of each of the following compounds.

a) propylene b) acetylene c) ethylacetylene d) ethylene
SOLUTIONS TO SAMPLE PROBLEMS:

1.1 a) pentane b) trichloromethane c) 2-butanol d) 3-methylpentane

e) 3-bromo-2-methylpentane f) 3-ethylhexane g) 5-isopropyl-3-methyloctane
h) 3,3-dibromo-1,1,1-trichlorobutane i) 2-ethyl-1-pentanol j) 2,5-dimethyl-1-hexene
k) 2,5,5-trimethyl-3-heptyne l) trans-1,2-dibromo-1-butene m) 2-ethyl-1-butene

1.2 a) 2,2-dimethylbutane b) 3,3-dimethyl-1-butanol

CH3 CH3
| |
CH3 CCH2 CH3 HOCH 2 CH2 CCH3
| |
CH3 CH3

c) 4-ethyl-2,2-dimethylhexane d) 1,2-dibromo-2-methylpropane
CH3 CH2 CH3 CH3
| | |
CH3 CCH2 CHCH 2 CH3 CH2 CCH3
| | |
CH3 Br Br

e) 4-methyl-2-pentyne f) cis-1-bromo-2-pentene
CH3 C≡CCHCH 3 BrCH2 CH2 CH3
|
CH3 C C
H H

2.1 a) cycloheptane b) isopropylcyclopentane

c) 2-methylcyclobutanol d) 1,4-dichlorocyclohexene

2.2 a) 1,3-dimethylcyclobutane b) 4-neopentylcyclohexanol c) 4-isopropylcyclohexene

CH3
|
CH3 CH3 HO CH2 C-CH3
|
CH3
3.1 a) bicyclo[4.3.0]nonane b) bicyclo[3.2.1]octane
c) 7-chlorobicyclo[4.1.1]octane d) 1,6-dimethylbicyclo[3.2.0]heptane

3.2 The structures are:

CH2 CH3

a) b) CH(CH 3 )2 c)

CH2 CH3
4.1 a) ethyl alcohol b) propyl chloride c) neopentyl alcohol d) tert-butyl fluoride

4.2 a) methyl iodide b) isobutyl alcohol c) isopropyl alcohol d) sec-butyl bromide

CH3 I (CH3 )2 CHCH 2 OH (CH3 )2 CHOH CH3 CHBrCH 2 CH3

5.1 a) cyclopentyl alcohol b) cyclohexyl alcohol c) cyclobutyl bromide

5.2 a) cyclopropyl chloride b) cyclohexyl iodide

Cl I

6. a) propylene b) acetylene c) ethylacetylene d) ethylene

CH3 CH=CH 2 H-C≡C-H CH3 CH2 C≡C-H H2 C=CH 2

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