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Chemistry Module IV Organic

Chemistry I for IIT JEE main and


advanced Rajesh Agarwal McGraw Hill
Education Rajesh Agarwal
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Rajesh Agarwal

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Organic Chemistry-I

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Dedicated to a great Chemistry teacher,
my father,
Late Shri J. P. Agarwal
Preface

Organic Chemistry-I has been written for students who want to undertake well-rounded preparations for JEE (Main as
well as Advanced). It is imbued with the essence of 20+ years’ experience of coaching and mentoring IIT aspirants. It
has been written in a manner that students may learn the concepts from a basic level. It will also sharpen the concepts of
learners who have already prepared well.
This book has nine chapters with all the important concepts and multiple choice questions with solutions for clear
understanding of concepts. The chapters have been classified into sections such as key points, solved examples, exercises
and solutions.
Exercises given at the end of every chapter are further categorised into three difficulty levels of questions and their
patterns as asked in the JEE along with the previous years’ questions with solutions.
• Level-1 has the questions mainly suitable for JEE-Main exam
• Level-2 contains slightly difficult questions suitable for JEE-Advanced
• Level-3 has the toughest questions of various patterns asked in JEE-Advanced (such as more than one correct
answer, comprehension, match the column and single-digit integer)
The content of this book has been laid in a manner that will engage students meaningfully and in turn help them to
acquire deep knowledge of concepts. This book stands out in terms of satisfying the need of students for a focussed study
material for specific competitive exams like JEE-Main and Advanced.
I have put my best effort towards making the book error free. Nevertheless, constructive suggestions and feedback from
readers are welcome as it is important for the continuous improvement of the same.
Acknowledgements

This work would not have been possible without the support of my colleagues, friends and family.
I express my gratitude to the publisher for providing this opportunity and the editorial team for the immensely painstaking
task of copyediting and typesetting. My thanks also go to the scores of students who have helped me in learning for more
than 20 years. I also thank my wife, Sunita, for allowing me to spend time on this work despite an already hectic coaching
schedule.
Contents

About the Author ii


Preface vii
Acknowledgements ix
1. Classification and Nomenclature 1.1-1.44
2. Isomerism 2.1-2.54
3. General Organic Chemistry 3.1-3.60
4. Aliphatic Hydrocarbons (Alkanes) 4.1-4.26
5. Aliphatic Hydrocarbons (Alkenes) 5.1-5.42
6. Aliphatic Hydrocarbons (Alkynes) 6.1-6.24
7. Aromatic hydrocarbon (Arenes) 7.1-7.36
8. Purification and Characterisation of Organic Compounds 8.1-8.14
9. Environmental chemistry 9.1-9.14
Chapter 1
Classification and Nomenclature

Introduction
Organic substances are mainly found in living organisms like animals and plants.
The first synthesised organic substance is urea discovered by Whölar.
Organic substances mainly contain C and H and one or more additional elements like
oxygen, nitrogen, sulfur, phosphorous, halogens.
Catenation: The self-linking tendency by covalent bond in non-metals whose co-valency
is 2 or more than 2, known as catenation.
Carbon shows to maximum catenation property.
Maximum covalency of carbon is 4.
Carbon atoms join together by single, double or triple bond that gives carbon
Skeleton.

Classification of Organic compounds


All the known organic compounds have been divided in the following manner:

Organic compounds

Open chain compound Closed chain compound


Aliphatic compound Ring compounds
Acyclic compound Cyclic compounds

Saturated Unsaturated Homocyclic (Carbocyclic) Heterocyclic at least


CH3 CH3, CH2 CH2, Only C-atoms involved in one hetero atom involved
CH3 O CH 3, HC CH, ring formation in ring formation
CH3 CH 2 OH CH2 C CH2
e.g., N,O,S,P, etc.

Alicyclic Aromatic Alicyclic Aromatic


O O

O O S
O
O

O N N
Benzenoid Non-benzenoid NH
O
1.2 | Organic Chemistry Module I

Benzenoid Non-benzenoid
OH

The four valencies of carbon atom can be represented by the following way:
No. of Bond
Structure s bonds p bonds Hybridisation Shape Bond Angle
angles

Tetrahedral 6
C 4 0 sp3 109°28¢
(Non planar)

3 1 sp2 Planar (Trigonal) 120° 3


C
C 2 2 sp Linear 180° 1
C 2 2 sp Linear 180° 1

Determination of Hybridisation
• It is based upon ‘electron pair’ (ep) of hybrid atom.

e.p. = s ve) charge

No. of ep. 2 3 4
2
Hybridisation sp sp Sp3

Identification of carbon
1. Primary, Secondary, Tertiary, and Quaternary carbon
There are four types of carbons in the carbon chain.
(i) Primary carbon: A carbon atom attached to one (or no) other carbon atom is termed primary carbon or 1° carbon
atom.
(ii) Secondary carbon: A carbon atom attached to two other carbon atoms is termed secondary carbon or 2° carbon
atom.
(iii) Tertiary carbon: A carbon atom attached to three other carbon atoms is termed tertiary carbon or 3° carbon
atom.
(iv) Quaternary carbon: A carbon atom attached to four other carbon atoms is termed quaternary carbon or 4° carbon
atom.

C C

C C C C C

1°C 3°C 2°C C 4°C


Primary tertiary secondary Quaternary
Classification and Nomenclature |   1.3
Identification of Hydrogen
• Nature of H, just same as the nature C through which it is joined
The hydrogen atoms attached to primary, secondary and tertiary carbon atoms are correspondingly termed as primary,
secondary and tertiary hydrogen atoms respectively.

Type of Structure
1. Normal structure – prefix “n” is used for unbranched carbon chain
2. Iso structure – prefix “iso” is used when one methyl group is attached on 2nd carbon from either terminal.
3. Neo structure – prefix “neo” is used when two methyl group is attached on 2nd carbon from either terminal.

Homologous series
Series of such compounds in which the various members have similar structural features and similar chemical properties
but the successive members differ in their molecular formula by CH2 known as homologous series.

General Characterstics
(i) All compounds in the series composed of some element
(ii) All compounds have same general formula.
(iii) Molor mars of adjacent member differ by 14.
(iv) All compounds in the series have similar chemical properties however different physical properties.

Naming of organic substance


(1) Common name or Trivial name
(2) Derived name
(3) I.U.P.A.C Name and Jeneva Names system
[1] Common name or Trivial name system
Type 1 Common name based on source:
• This type of nomenclature is based on their source of origin known as trivial name.
Substance Source of origin Trivial Name
CH4 Marsh places Marsh gas
CH3–OH Destructive Distillation of wood Wood spirit
H–C–OH Red ant (Formica) Formic acid
O
CH3—COOH Acetum (Vinegar) Vinegar
CH3—CH2—CH2—COOH Butter Butyric acid
NH2–C–NH2 Urine Urea (Carbamide)
O
CH3–CH–COOH Lactum (Milk) Lactic acid
OH

Type 2 Common name radicals

+H
C H C G
+G
functional group
Hydrocarbon Group
(Radical)
1.4 | Organic Chemistry Module I
Radical (– R)
• It is framework of only C and H
• It is formed by the removal of at least one H from hydrocarbon
• It influences physical property of substance.

Type of Radical
(1) Aliphatic Radical: Those radical which are formed by aliphatic hydrocarbon.
Aliphatic radical

C C C C C C
From alk ane From alk ane From alk yne

Cn H2n+2 Cn H2n Cn H2n–2

–H –H –H

Cn H2n+1 Cn H2n–1 Cn H2n–3


alkyl alkenyl alkynyl

Univalent Radical
1. Alkyl Radical
• Common name = Alk + yl
Alk meth eth prop but pent hex hept oct non dec

No of carbon 1C 2C 3C 4C 5C 6C 7C 8C 9C 10C

–H
(i) CH4 CH3
Methane Methyl (me)

–H
(ii) CH3 CH3 CH3 CH2
ethane ethyl (et)

CH3 CH2 CH2


n-propyl
(iii) CH3 CH2 CH3
1° 2° 1°
CH3 CH CH3
Prop ane
2° 2° Iso-propyl
Type of H = 2

–H
(iv) C4H10 C4H9
butane butyl = 4

CH3 CH2 CH2 CH2


1° 2° 2° 1°
CH3 CH2 CH2 CH3 n-butyl
n-butane CH3 CH CH2 CH3
Type of H = 2
s-butyl
Classification and Nomenclature |   1.5
CH3
CH3 CH CH2 CH2

CH3 Iso butyl
CH3 CH CH3
1° 3° 1° CH3
CH3 C CH3
iso-butane
Type of H=2 t-butyl

–H
(v) C5H12 C5H11
Pentane Pentyl (8)

CH3 CH2 CH2 CH2 CH2


1° 2° 2° 2° 1° n-pentyl
CH3 CH2 CH2 CH2 CH2
*
CH3 CH2 CH2 CH CH3
n-pentane
Type of H = 3 2° active amyl

CH3 CH2 CH CH2 CH3


2° amyl
CH3
CH3 CH CH2 CH2
1° iso pentyl
CH3
CH3 CH CH2 CH3 CH3
1° 3° 2° 1° *
CH3 CH CH CH3

Isopentane 2° iso active amyl


Type of H = 4 CH3
CH3 C CH2 CH3
3° pentyl
CH3
CH2 CH CH2 CH3
*
active amyl

1°CH CH3
3

CH3 C CH3 CH3 C CH2–



1°CH 1° CH3
3
neo pentane neopentyl
Type of H = 1

Note: Chiral C(*) containing 5C alkyl always named as active amyl


1.6 | Organic Chemistry Module I
2. Alkenyl Radical
Common name = alk + en + yl
CH2 = CH2 CH2 = CH
Ethylene Vinyl or Ethenyl

CH3 CH = CH
CH3 CH = CH2 n-propenyl
1° 2° 1° CH3 C = CH2
iso propenyl

CH2 CH = CH2
allyl
–H
CH3 CH = CH CH3 CH3 CH = CH CH2
Crotyl
3. Alkynyl Radical
Common name = alk + yn + yl
CH CH CH C
Ethyn e ethynyl
CH3 C C
CH3 C CH Propynyl

CH2 C CH
Propargyl
• Polyvalent Radical
Case-I: Removal of more than one H from same carbon.
–H –H
CH3 CH3 CH3 CH2 CH3 CH (CH3 C )
Ethane Ethyl Ethylidene Ethylidyne
(Univalent) Bivalent (divalent) Trivalent

Case-II: Removal of more than one H from adjacent carbon.


CH2 CH2 , CH3 CH CH2
ethylene propylene

(2) Alicyclic radical


CH2 CH2 C
CH2 CH2 CH2 CH2 CH2 CH2
Cyclopropane Cyclopropyl Cyclopropylidene

(3) Aromatic Radical


–H H H
H
H H
H H –H
H
H H ( C6H5)Phenyl

H
(C6H6)benzene
–2H

P-phenylene m-phenylene o-phenylene


Classification and Nomenclature |   1.7

CH2 CH C

CH3
H H Benzyl Benzal Benzo

H H CH3 CH3 CH3


H
Toluene

o-tolyl m-tolyl p-tolyl


Type 3 Common name of alkane:
• It is given by using prefix n, iso, neo.
Type 4 Common name of alkene:
• Common name = Alkylene

• In more than 3 carbon containing alkene


(i) For straight chain-prefix a, b, g, d, etc. is used to locate the position of double bond at 1, 2, 3, 4. carbon, respec-
tively from nearest terminal.
(ii) For branched alkene- iso, neo prefix used but only when double bond at terminal carbon.
Type 5 Common name for functional group containing substance.
Functional group

Non terminal group Terminal group


OH C , X COOH, CH = O, CN etc.
O
Case-I: Substance containing non terminal functional group
• Common name Æ Name of radical + Name of functional group.
S.No. Functional group Group name
1 –SO3H Sulphonic acid
2 –X (–F, –Cl, Br, –I) halide
3 –OH alcohol
4 –SH thio alcohol
5 –O– ether
6 –S– thio ether
7 C ketone

O
8 NH2 NH , N amine

• In polyvalent group, more than one radical present.


(i) More than one same radical, expressed by numerical prefix
2 – di, 3 – tri, 4 – tetra, etc.
(ii) Different radical always write in alphabet manner.
1.8 | Organic Chemistry Module I
Case-II: Substance containing terminal functional group
• Common name = prefix + suffix
Prefix–It is based on of total number of carbon present
Number of carbon 1C 2C 3C 4C 5C
Prefix Form Acet propion Butyr Valer

Special prefix
C = C — Cfn C – C = C — Cfn Ph – C = C – Cfn CH3 – CO – Cgr
Acryl Croton Cinnam Pyruv

Suffix Æ It is based on of terminal functional group.


S.No. Terminal functional group Suffix
1. — COOH ic Acid
2. C O ate

O
3. O ic anhydride
C C

O O
4. O yl chloride

C Cl
5. O Amide

C NH2

6. — CH = O Aldehyde
7. —C∫N O-nitrile/Cyanide
8. —N∫C O-isonitrile/isocyanide

Note: –CN and –NC are considered in both systems (Case I & Case II)
Type 6 Geminal/vicinal/ a-w type substance
Geminal compound Vicinal compound a-w type compound
x C C C
C C C
C C x x
x
x x    OH OH a-w type
Gem dihalide
vicinal dihalide vicinal dialohol
Glycol
Common name Common name Common name
Alkylidene + functional group alkylene + functional group poly methylene + functional group

Note: Poly word expressed number of CH2–groups.

No of CH2– 3 4 5
Poly Tri Tetra Penta

[2] Derived name system:


According to this system name of any compound is given according to the representative compound of the homologous
series. This system is reserved for following homologous series.
Classification and Nomenclature |   1.9

Series Name of Homologous series Name of Representative compound Structure of group


1 Alkane Methane
C

2 Alkene Ethylene >C = C<


3 Alkyne Acetylene –C∫C–
4 Alcohol Carbinol
C OH

5 Aldehyde Acetaldehyde
C CHO

6 Ketone Acetone
C C C
O
7 Carboxylic acid Acetic acid
C COOH

[3] IUPAC name system or Geneva name system:


1. A given compound can be assigned only one name.
2. A given name can clearly direct in writing of one and only one molecular structure.
3. The system can be applied in naming complex organic compounds.
4. The system can be applied in naming multifunctional organic compounds.
5. This is a simple, systematic and scientific method for nomenclature of organic compound.
IUPAC Nomenclature of Aliphatic Compounds:
The name of an organic compound consists of three parts:
• Word root
• Prefix
• Suffix
Word root: It is given on the basis of number of C in parent chain.
No of C 1C 2C 3C 4C 5C 6C 7C 8C 9C 10C 11C 12C 20C
Word root meth eth prop but pent hex hept oct non dec undec dodec Eicos

Prefix: It is given on the basis of the side chain in parent chain


(i) All alkyl radical works as side chain
(ii) Some of the given functional group always behave as side chain

S.No. Functional group Side chain (prefix)


1. –X Halo
2. –OR Alkoxy
C C
3. Epoxy
O
4. –NO2 Nitro
5. –N=O Nitroso
6. –N=N– Azo

(iii) Rest functional group (except above) may be work as side chain according to their priority with respect to other
functional group.
1.10 | Organic Chemistry Module I
Suffix
Primary suffix: If is given by the bonding nature between C–C in selected parent chain.

S.No. Bonding nature (PC) 1° Suffx


–C–C–
1. ANE
(All single bond)
–C=C–
2. ENE
(Al least one)
– C ∫ C–
3. YNE
(Al least one)
–C=C–C ∫ C–
4. (ENYNE)
(Both (=) bond and ( ∫ ) bond

Secondary suffix: It is given on the basis of principal functional group present in parent chain.
• 2° Suffx always written after 1° Sufix as follows.

AN E
EN E 2° suffix
YN E
ENYN E

Note: ‘e’cancelled only when 1st alphabet of 2° suffix is vowel (a,i,e,o,u)

Arrangement of prefixes, Root word and Suffixes:

IUPAC Name = prefix (es) + word root + Primary suffix + Secondary suffix

Priority table of functional group (selection of Principal functional group)


Functional group Prefix 2° Suffix
—COOH carboxy Oic Acid
—SO3H sulpho Sulphonic Acid
O O

C C – Oic anhydride

O
O
alkoxy carbonyl or carbo alkoxy Oate
C OR
O
chloro formyl or Chloro carbonyl Oyl chloride
C Cl
O
carbamoyl Amide
C NH2

—C ∫ N cyano Nitrile
—N ∫ C isocyano Iso carbonitrile
—CH=O formyl / oxo AL
O NH2
keto or oxo ONE
C
—OH hydroxy OL
—SH mercapto Thiol
—NH2 amino Amine
Classification and Nomenclature |   1.11
Salient features of priority table:
(1) Above given table shows decreasing priority of functional group.
(2) When only one of above functional group is present in parent chain, then this functional group behave as 2° suffix,
known as Principal Functional group.
(3) When more than one of above functional groups is present then higher priority functional group is the principal
functional group (2° suffix) and rest are least priority functional groups will be represented by prefix.
(4) Mostly 2° Suffix C will be included in word root.
(5) Prefix, C never included in word root except only ketone.

IUPAC Naming of Side chain (radical)


• Numbering always start from free valency containing carbon
• Ending always with ‘yl’
Simple radicals
1 2 3
–CH3 –CH2–CH3 CH2 CH2 CH3
Methyl Ethyl Propyl
Complex radicals CH3
CH3 CH3 2 1
CH3 C
CH CH3, CH CH CH3,
1 2 1 2 3 CH3
Methyl ethyl (isopropyl) 2-Methyl propyl 1,1-di methyl ethyl
1 1 2 1
CH2 Cl CH2 CH2 Br CH2 CH = O
Chloro methyl 2-Bromo ethyl Formyl Methyl
1 2 1 2 3
CH2 CH2 COOH CH2=CH– CH2 CH = CH2
2-Carboxy ethyl ethenyl (vinyl) 2-propenyl (Allyl)
1 2
1 2 3 1 2 CH3 C CH3
CH2 CH CH CH3 CH
2-propynyl (propargyl) Ethylidene 1-Methyl ethylidene

Important Points
1. Repetition of side chain expressed by numerical prefix 2-di, 3-tri, 4-tetra etc.
2. Repetition of complicated side chain expressed by numerical prefix 2-bis, 3-tris, etc.
3. Different side chain is always written in alphabet manner
4. If alphabet order is same then least locant number side chain written at Ist place
5. If di, tri prefix included in complicated side chain then these prefixes include in alphabet comparison.

Rules of I.U.P.A.C Naming


Rule 1: Selection of parent chain (PC)
Parent chain must be contain following in given order of priority:

Maximum number of Maximum number Maximum number Maximum number Lowest set of
> > > >
Principal functional group of multiple bond of carbon of side chain locant number

Note: For open chain substance selection always start and end at terminal carbon.
Rule 2: Least locant number rule
Numbering of parent chain start from the terminal that has through which functional group, multiple bond, side chain must
have least locant number or lowest set of locant number in given order.
1.12 | Organic Chemistry Module I
Principal functional group > Multiple bond > side chain
Rule 3: Alphabet rule
This rule comes into existence only when least locant number rule does not apply.
When different member of similar category like functional group, multiple bond, side chain are present at equivalent
position from either of terminal, then alphabetically preferred member of same category gets least locant number.

Special case
1. Use of some special suffix:
When more than two similar terminal functional groups are directly attached with Parent chain or directly attached
with ring then according to latest IUPAC convention carbon atom of these functional group is not included in the
parent chain even that they work as a Principal functional group (2° suffix)
• Latest 2° suffix of terminal functional group are given below:

Functional group 2° suffix


COOH Carboxylic acid
COOR Carboxylate
COCl Carbonyl chloride
CONH2 Carboxamide
C∫N Carbo nitrile
CH=O Carbaldehyde

2. Use of some special prefix:


In IUPAC naming O, S, N, Se atom can also be included in parent chain like carbon. The presence of these atom
is expressed with special prefix given below with suitable locant no.

Atom Prefix
O Oxa
S Thia
N Aza
Se Selena

IUPAC Nomenclature of Alicylic Compounds


(1) Rules 1,2,3 apply as usual like in open chain.
(2) Additional prefix cyclo is used just before word root.
(3) Numbering of cyclic parent chain starts at any C of ring according to rule-2 and 3
(4) We never count number of C of ring and outside ring simultaneously
(5) When both open and closed chain have same feature than closed chain will be selected as a parent chain.
IUPAC Nomenclature Aromatic Compounds:
1. The common name of aromatic substance is also recognised as their I.U.P.A.C. name.
2. When benzene ring selected as parent chain

Word root + 1° suffix fi Benzene

IUPAC Nomenclature of Bicyclo Compounds:


Such cyclic substance two lines are fused together in such a way that they have two common tertiary carbon with ring or
one side is common, known as bicyclo substance.
Classification and Nomenclature |   1.13

C
Bridge carbon
C C
X C y Z Bridge head carbon (b.h.c)
C C
C

General rules of naming:


1. Additional prefix bicyclo is used
2. In big bracket write number of bridge carbon of all three direction individually in decreasing order separated by
commas.
3. word root is given on the basis of total number of carbon present in a bicyclic part

Number of C in bicycle ring = x + y + z + 2

4. Numbering of Bicyclo ring.


(i) Numbering always starts from one of the b.h.c (Bridge head carbon).
(ii) It is proceed along higher number of bridge carbon site to next b.h.c.
(iii) Again proceed along second higher bridge, carbon site.
(iv) Finally terminate along least bridge carbon site.
IUPAC Nomenclature of Spiro compounds:
Such cyclic substance in which two rings are fused together in such a ways that they have only one common carbon, is
known as spiro substance.

C C
x C y
C C
4°C (spiro) common carbon

General rule of naming:


1. Additional prefix spiro is used
2. In big bracket write number of carbon of two rings individually except common carbon in increasing order.
3. Word root is given on the basis of total number of carbon present in a spiro ring.

Number of C in spiro ring = x + y + 1

4. Numbering of spiro ring.


(i) Numbering always starts from adjacent common carbon in smaller ring.
(ii) Proceed along smaller ring to spiro carbon.
(iii) Finally terminate along bigger ring.
1.14 | Organic Chemistry Module I

Solved Example
1. Ethyl methyl vinyl amine has the structure– 3rd member n = 6
(1) CH3CH2 N CH2CH=CH2 Molecular formula = C6H2×6–4 = C6H8
5. Which of the following is not correctly matched?
CH3
(1) Acetonitrile CH2 = CHCN
(2) CH3CH2 N CH=CH2
(2) Allyl chloride CH2 = CH – CH2Cl
CH3 (3) s-Butyl group CH3 CH C2H5
(3) CH2=CH N CH=CH2 Cl
(4) Ethylidene chloride CH3 CH
Cl
CH3 Sol. [1]
(4) CH3 N CH=CH2 Aceto nitrile Æ CH3–C ∫ N but given CH2 = CHCN
so it is incorrectly matched.
CH3
6. The correct IUPAC name of the following compound
Sol. [2]
is
Ethyl Æ –C2H5
Methyl Æ –CH3
Vinyl Æ –CH = CH2
3-alkyl containing amine must be 3° amine

CH3CH2 N CH=CH2
(1) 3-ethtyl-3-isopropyl-4-tertiarybutyl hexane
CH3 (2) 3, 3, 4-triethyl-2, 5, 5-trimethyl hexane
2. Derived name of CH2=CH–CH2CO–CH3 is (3) 3, 4-diethyl-4-isopropyl-2, 2-dimethyl hexane
(1) 1-Pentene-1-one (2) Allyl methyl ketone (4) 3, 4, 4triethyl-2, 2, 5-trimethyl hexane
(3) 4-Pentene-2-one (4) Vinyl acetone Sol. [4]
Sol. [4] 5 6

CH2= CH CH2 C CH3 3 4


2
O
(Sidechain) Vinyl acetone 1
(representative compound)
Parent chain must be contain maximum number of
3. The hybrid state C-atoms which are attached to sin- side chain.
gle bond with each other in the following structure
7. What is the IUPAC name of the following
are– CH2 = CH—C ∫ CH
compound?
(1) sp2, sp (2) sp3, sp C N
(3) sp2, sp2 (4) sp2, sp3
Sol. [1] CH3 C C CH2 C CH2 OH
CH2 = CH C CH CH3
(1) 2-cyano-2-methyl hex-4-yne--ol
ep=3+0+0 ep=2+0+0 (2) 2-hydroxy methyl-2-methyl-hex-4-yne-nitrile
sp2 sp (3) 2-methyl-2-hydroxy methyl hex-5-yne-nitrile
4. The third member of the family of alkenynes has (4) 1-cyano-2-hydroxymethyl-2-methyl-4-hexyne
molecular formula- Sol. [3]
(1) C6H6 (2) C5H6 1
C N
(3) C6H8 (4) C4H4 6 5 4 3 2
Sol. [3] CH3 C C CH2 C CH2 OH
General formula of alkenyne Æ Cn H2n–4 CH3
For 1st member n = 4
2-methyl-2-hydroxy methyl hex-5-yne-nitrile
2nd member n = 5
Word root = 6C (Hex)
Classification and Nomenclature |   1.15
Side chain = –CH 3 (methyl) and –CH 2–OH • Priority order Æ
(Hydroxymethyl) functional group > Multiple bond > side chain.
1° suffix Æ yne C
2° suffix Æ –CN (Nitrile) 1 2 3 4 5 6 7 (correct)
C C=C C C C C
Principal functional group must have least locant 7 6 5 4 3 2 1 (wrong)
number. O
8. Which is the correct structure 5, 6, 6-trimethyl-3- 6-methyl hept -2-en-4-one
heptyne? O
11. The IUPAC name of HO is–
(1) (2) OH
(1) 3-hydroxybutanoic acid
(2) 4-methyl-2-oxo-1, 4-butanediol
(3) (4)
(3) 1, 4-dihydroxy-4-methyl-2-butanone
Sol. [1] (4) 1, 4-dihydroxy-2-pentanone
Parent chain must have 7C Sol. [4]
1 suffix Æ yne at 3ed C Principal functional group ketone must have least
Three methyl side chain at 5, 6, 6 locant number.
6 4 2
–OH group works as side chain.
O
7 5 1 5
3
HO
2 3 4
1 OH
9. The correct IUPAC name of the compound is
OH 1, 4-dihydroxy-2-pentanone
12. The correct IUPAC name of the compound is
SO3H
Br I

(1) Cyclo pent-1-en-3-ol
(2) Cyclo pent-2-en-1-ol CH3

(3) 3-hydroxy cyclo pentene
(1) 2-iodo-3-methyl-5-bromocyclo pentane sulphon-
(4) None of these
ic acid
Sol. [2]
(2) 5-Bromo-4-methyl-5-iodocyclo pentane sulphon-
OH
1
ic acid
2 5 (3) 5-Bromo-3-iodo-2-methylcyclo pentane sulphon-
ic acid
Principal functional group have proirity
(4) 5-Bromo-2-iodo-3-methylcyclopentane sulphon-
3 4than multiple bond (rule-2)
ic acid
Cyclo pent-2-en-1-ol
Sol. [4]
10. The correct IUPAC name of the compound is • Cyclic chain selected as parent chain.
C • –SO3H is principal functional group.
C C=C C C C C • Br, –I, –CH3 are side chain.
• Apply least locant number rule.
O
(1) 2-methyl hept-5-en-4-one SO3H
Br 1 I
(2) 6-methyl-4-oxo-2-heptene 5 2
(3) 6-methyl hept-2-en-4-one
(4) None of these 4 3
CH3
Sol. [3]
• Numbering of parent chain according to least 5-Bromo-2-iodo-3-methylcyclopentane sulphonic
locant number rule. acid
1.16 | Organic Chemistry Module I
13. The correct IUPAC name of the compound is (1) 1-phenyl ethyl ethanoate
CH=CH COOH (2) 1-acetoxyethylbenzene
(3) ethoxycyclohexyl ketone
(4) ethyl cyclohexanecarboxylate
Sol. [1]
(1) Cinamic acid • Principal functional group is ester
(2) 3-phenyl-2-propenoic acid • Open chain selected as parent chain.
(3) b-phenyl acrylic acid 2¢
CH3 O
(4) 1-phenyl-2-propenoic acid
Sol. [2] CH O C CH3

• Open chain contains –COOH group so it is se- side chain parent chain
lected as parent chain.
1-phenyl ethyl ethanoate
CH=CH COOH 16. The correct IUPAC name of the compound is
3 2 1
OH
Side Chain (Phenyl)
CH3 CH CH C CH2 CH3

3-phenyl-2-propenoic acid OH CH2 CH3

14. The IUPAC name of the following compound is OH


(1) 3-hydroxy methyl-4-methyl hexane-2,4-diol
CHO (2) 2-(1-hydroxy ethyl)-4-methyl pentane-1,3-diol
(3) 4-hydroxy methyl-3-methyl hexane-2,4-diol
(4) None of these
C Cl Sol. [1]
Br • Parent chain must have maximum number of
O
principal functional group (–OH) with maximum
(1) 4-bromo-3-chlroformyl benzaldehyde number of carbon.
(2) 2-bromo-5-formyl benzene carbochloride • Numbering of parent chain according to least
(3) 2-chloro carbonyl bromobenzene locant number rule.
(4) 6-bromo-3-formylbenzo-3-yl chloride OH
1 2 3 4 5 6
Sol. [2] CH3 CH CH C CH2 CH3 Parent chain
• Benzene ring must be selected as parent chain.
OH CH2 CH3
• C Cl group is principal functional group.
OH Side Chain
O
• –CH=O, –Br, are side chain. 3-hydroxy methyl-4-methyl hexane-2,4-diol
• Numbering of benzene ring according to least lo- 17. The correct IUPAC name of the compound is
cant number rule.
HOOC CH CH COOH
CHO
5 NH2 CH=O
4 6
(1) 3-amino-2-formyl butane-1, 4-dioic acid
1
3 (2) 3-amino-2, 3-dicarboxy propanal
2 C Cl
Br (3) 2-amino-3-formyl butane-1, 4-dioic acid
O (4) 1-amino-2-formyl succinic acid
2-bromo-5-formyl benzene carbochloride Sol. [3]
CH3 1 2 3 4
O
HOOC CH CH COOH alphabet rule NH2—amine
15. The IUPAC name of CH O C CH3
is NH2 CH=O
Classification and Nomenclature |   1.17
Although CHO group is before NH2 but after deciding O O
top most in order group (COOH) next groups are
CH3 C CH CH CH2 CH2 Br
arranged alphabetically. So numbering is done from 1 2 3 5 6 7
left to right. C
4
Prefix for NH2– group is amino and for CHO– group CH3 CH3
is formyl.
7-bromo-3, 5-epoxy-4,4-dimethyl-2-heptanone
18. The correct IUPAC name of the compound is

CH2 COOH 20. The correct IUPAC name of the compound is


CH3–NH–CH=O
CH COOH
(1) N-formyl methanamine
CH2 COOH (2) N-methyl methanamide
(3) Methylanino methanal
(1) 1, 2, 3-tricarboxy-propane
(4) N-methy–N–formyl amino methane
(2) 3-carboxy-1, 5-pentane dioic acid
Sol. [2]
(3) propane-1, 2, 3-tri carboxylic acid CH3 NH CH=O
(4) none of these
Sol. [3] CH3 NH C H
When more than two terminal functional groups O
are directly attached with parent chain then no such
group carbon included in word root; according to the • Principal functional group is amide (–CONH–)
latest IUPAC convention 2° suffix is carboxylic acid 21. The correct IUPAC name of the compound is
(– COOH)

1 CH COOH
2
N
2 CH COOH
3 CH COOH (1) N-Ethyl-N, 3-dimethyl-2-amino pentane
2
(2) N-ethyl-N, 3-dimethyl-2-pentanamine
propane-1, 2, 3-tri carboxylic acid (1st Choice) (3) N-Ethyl-N, 3-Dimethyl-4-pentanamine
3-carboxy-1, 5-pentane dioic acid (2nd choice) (4) 2-(Ethylmethyamino)-3-methyl pentane
1, 2, 3-tricarboxy-propane (3rd choice) Sol. [2]
1
19. The correct IUPAC name of the compound is
O 2 4
O 3
N 5
CH3 C CH CH CH2 CH2 Br
C N-ethyl-N, 3-dimethyl-2-pentanamine
CH3 CH3 22. A compound named 5-(1-cyanoethy)-2-methyl
hexanoic acid has something wrong according to
(1) 7-bromo-3, 5-epoxy-4,4-dimethyl-2-heptanone IUPAC. What is its correct IUPAC name?
(2) 7-bromo-3, 5-epoxy-4, 4-dimethyl-2-oxo (1) 5-ethyl cyanide-2-methyl hexanoic acid
heptane (2) 6-cyano-2, 5-dimethyl heptanoic acid
(3) 1-bromo-3, 5-epoxy-4,4-dimethyl-6-heptanone (3) 6-cyano-5-methyl-2-heptanoic acid
(4) 1-bromo-4, 4-dimethyl-5-oxo-heptane (4) 6-carboxy-2, 3-dimethyl heptanenitrile
Sol. [1] Sol. [2]
• Numbering of parent chain according to the least • Parent chain must have 6C with COOH group.
locant number rule. • Side chain CH CH3 and CH3
• Priority order Æ CN
functional group > Multiple bond > side chain. • So that possible structure is
1.18 | Organic Chemistry Module I
C C N
6 5 4 3 2 1 1 2° suffix
C C C C C COOH 2 6
1¢ C CN 3
4
5 CH=O
2¢ C
• Correct numbering of parent chain is 5-formyl cyclo hex-2-en-carbonitrile
24. The correct IUPAC name of the compound is
C
5 4 3 2 1
C C C C C COOH
6C CN (1) Bicyclo [4, 2, 0] octane
(2) Bicyclo [2, 4, 0] octane
7C (3) Bicyclo [4, 2, 0] hexane
6-cyano-2, 5-dimethyl heptanoic acid (4) None of these
23. The correct IUPAC name of the compound is Sol. [1]

C N
Bicyclo [4, 2, 0] octane
25. The correct IUPAC name of the compound is
CH=O OH
5-formyl cyclo hex-2-en-carbonitrile

(1) 3-cyano cyclo hex-5-en-carbaldehyde


(2) 5-cyano cyclo hex-3-en-carbaldehyde (1) Spiro [3,2] hexan-4-ol
(2) Spiro [2,3] hexan-2-ol
(3) 5-formyl cyclo hex-2-en-carbonitrile
(3) Spiro [2,3] hexan-4-ol
(4) 3-formyl cyclo hex-5-en-carbonitrile (4) Spiro [3,2] hexan-2-ol
Sol. [3] Sol. [3]
• Numbering of parent chain according to least OH
locant number rule. 4 1

• Priority order Æ 5
3
2
functional group > Multiple bond > side chain. 6
Spiro [2,3] hexan-4-ol

Exercise 1
1. Identify which functional group is Not present in the 3. The common name of given ester is–
following compound? CH3 CH3
O O
CH3 CH C O C CH3
NH
O CH3
O O
(1) Neo butyl isobutyrate (2) t-Butyl n-butyrate
(1) Ketone (2) Ester (3) t-Butyl isobutyrate (4) Iso butyl isobutyrate
(3) Amide (4) Ether CH3 CH3
2. The number of olefinic bonds in the given compound
4. The derived name of CH3 C C OH is
is–
CH2 CH C CH CH C N CH3 C2H5
O (1) t-Butyl ethyl methyl carbinol
(1) 2 (2) 3 (2) t-Butyl ethyl methyl methanol
(3) 1 (4) 4 (3) t-Butyl methyl ethyl carbinol
(4) t-Butyl methyl ethyl methanol
Classification and Nomenclature |   1.19
5. Numbers of 3° carbon and 2° hydrogen respectively 12. In the following compound, group designated as
in the following structure are: A, B, C will be numbered as:
Me H H Et
CH3 A
Et C C C C Me

Me Et Me Me
OH B
(1) 3, 6 (2) 2, 4 CH
(3) 2, 6 (4) 1, 6
CH3 CH3 C
6. Which is true regarding cinnamaldehyde?
(1) All carbon have same hybridisation
(1) 1, 2, 4 (2) 4, 2, 1
(2) It is non-polar
(3) 5, 1, 2 (4) 3, 1, 6
(3) IUPAC name is phenyl propenal
(4) It is an aromatic aldehyde Cl
7. Give the IUPAC name of an alkane with the formula CH3
C8H18 that has only primary hydrogen atom 13. IUPAC Name of is:
(1) 2, 2, 4, 4-tetra methyl butane Br C2H5
(2) 2, 2, 3, 3-tetra methyl butane
(3) 2, 3-dimethyl hexane (1) 4-Bromo-6-chloro-2-ethyl-1-methylcyclohex-1-
(4) octane ene
8. The IUPAC name of the following compound is: (2) 5-Bromo-1-chloro-3-ethyl-2-methylcyclohex-2-
ene
OC2H5
O (3) 5-Bromo-3-chloro-1-ethyl-2-methylcyclohex-1-
ene
O
(4) 1-Bromo-5-chloro-3-ethyl-4-methylcyclohex-3-
(1) 3-methoxy ethylpropanoate ene
(2) ethyl4-methoxybutanoate 14. The correct structure of cyclobutylmethyl cyclopen-
(3) 1,4-diethoxybutane tane is
(4) 4-methoxy-ethylbutanoate
(1) CH2
9. The correct decreasing order of priority for the func-
tional groups of organic compounds in the IUPAC
system of nomenclature is CH3
(1) –SO3H, –COCl, –CONH2, –CHO (2)
(2) –CHO, –COCl, –SO3H, –CONH2
(3) –CONH2, –CHO, –SO3H, –COCl CH3
(4) –COCl, –SO3H, –CONH2, –CHO
10. The IUPAC name of O is (3)
(1) 2-butenyl ethyl ether (2) 3-ethoxy-2-butene
CH3
(3) 3-oxa-5-heptene (4) 1-ethoxy-2-butene
CN (4)

11. The IUPAC name of is 15. What is IUPAC name of the compound shown
below?
O
OH
(1) 2-methyl-3-(1-methylethyl)-4-oxopentanenitrile
(2) 4-cyano-3-(1-methylethyl)-2-pentanone Cl
(3) 3-Acetyl-2-cyano-4 -methylpentane
Cl
(4) 3-ethanoyl-2-methyl-3-(1-methylethyl) pentane
nitrile CH3
1.20 | Organic Chemistry Module I
(1) 3, 3-dichloro-4-methyl cyclohexanol (3) 6-(2-propenyl)-1, 7-decadiene
(2) 1, 1-dichloro-6-methyl-3-cyclohexanol (4) 4-(1-butenyl)-1, 8-nonadiene
(3) 1, 1-dichloro-2-methyl-5-cyclohexanol 22. IUPAC name of the given compound is
(4) 2, 2-dichloro-1-methyl-4-cyclohexanol
16. The systematic name of the given structure is
Br
(1) 2-methyl-1-(1¢-methyl propyl) cyclohexene
(2) 1-(1¢-methyl propyl)-2-methyl cyclohexene
Br (3) 2-Methyl-1-(1¢-methyl ethyl) cyclohexene
(1) 2, 5-dibromo-4, 7-diethyl octane (4) None of these
(2) 4, 7-dibromo-2, 5-diethyl octane 23. What is the correct IUPAC name of the following
(3) 5, 8-dibromo-6-methyl-3-methyl nonane compound?
(4) 2, 5-dibromo-4-ethyl-7-methyl nonane Cl
17. One of the names given below violates an important Br
IUPAC convention. Which is that name?
(1) 2-cyclopropyl-2-methyl propane Br
(2) 2-bromo-4-chlorobutane Cl
(3) Ethyl pentane Cl
(4) 3-bromo-1, 1-dichlorocyclohexane (1) 2, 5-dibromo-1-4-dichlorobenzene
Br
18. A hydrocarbon X has molar mass 84 but contains no (2) 1, 4-dibromo-3, 5-dichlorobenzene
double or triple bonds. Also X has no methyl locant. (3) 3, 5-dibromo-1,
Br 4-dichlorobenzene
How many different IUPAC name can be assigned (4) 1, 4-dibromo-2, 5-dichlorobenzene
Cl
to X? 24. The IUPAC name of the structure
(1) 2 (2) 3
(3) 4 (4) 6
19. Which of the following is an incorrect name accord-
ing to the IUPAC?
(1) 2-cyclopropyl butane
(2) 1-bromo-2, 2-dichloro cyclobutane is
(3) Cyclohexyl cyclohexane (1) 3-t-butyl-4-ethyl-5-isopropyl-2-methyl-3-heptene
(4) 1-cyclobutyl cyclobutane (2) 4, 5-diethyl-2, 2, 6-trimethyl-3-(1-methylethyl)-
20. What is the correct IUPAC name of the compound? 3-heptene
HO (3) 3-(1, 1-dimethyl ethyl)-4, 5-diethyl-2, 6-dimeth-
yl-3-heptene
(4) 4-ethyl-2, 2-dimethyl-3, 5-bis (1-methylethyl)-3-
heptene
CH = O
25. What is the correct IUPAC name of the compound
(1) 3-hydroxy cyclo hex-2-ene-1-carbaldehyde shown below?
(2) 5-hydroxy cyclo hex-2-ene-1-al
(3) 3-formyl-Cyclo hex-4-ene-1-ol OH
(4) 5-hydroxy cyclo hex-2-ene-carbaldehyde
21. What is the correct IUPAC name of the following
Br
compound?
(1) 3-bromo-3-octen-5-yne-2-ol
(2) 3-bromo-3-octen-6-yne-2-ol
(3) 6-bromo-5-octen-2-yne-7-ol
(1) 4-(1-propenyl)-1, 8-nonadiene (4) None of these
(2) 5-(2-propenyl)-3, 9-decadiene
Classification and Nomenclature |   1.21
26. What is correct IUPAC name of the following com- 30. Which is the correct structure of compound 1-meth-
pound? oxy-2-(2-methoxy ethoxy) ethane?
O O
(1) H3C O CH3
O CH3
(2) H3C O
(1) 4-(2-propynyl)-hepta-2, 5-diene O
(2) 4-(1¢-propynyl) hepta-2, 5-diene O O
(3) H3C CH
(3) 4-(1-propenyl)-2-heptene-5-yne
(4) 4-(1-propenyl)-5-heptene-2-yne O CH3
27. What is the correct IUPAC name of the compound? O O O
(4) H3C
NC
CN 31. What is the correct IUPAC name of

O O
CN
(1) 3-cyano-2, 5-dimethyl heptanedinitrile (1) 2-methoxy-3-(methyl propoxy) butane
(2) 5-cyano-3, 6-dimethyl heptanedinitrile (2) 2, 3-dioxy-2, 4-dimethyl butane
(3) 2, 5-dimethyl-1, 3, 7-heptanedinitrile (3) 3, 4, 6-trimethyl-2, 5-dioxa octane
(4) 2-methyl hexane-1, 4, 5 tricarbonitrile (4) both (1) and (3)
28. Which is the correct structure of 3-cyclohexylmethyl 32. The IUPAC name of CH3 O C CH2 C OH
butanamide? is:
O O
(1) CH3 (1) 2-carbomethoxy ethanoic acid
NH2 (2) 2-Acetoxy ethanoic acid
CH3 O (3) 2-Ethanoyloxy acetic acid
(4) 2-Ethanoyloxyethanoic acid
CH3
(2) 33. Correct IUPAC name of the given compound is:
NH2
Br
CH3 O
CH3
CH3 Cl OH
(3) NH
(1) 2-bromo-3-ethyl-4-chlorocyclobutanol
CH3 O (2) 4-bromo-1-chloro-3-ethylcyclobutanol
(3) 3-bromo-4-chloro-3-ethyl cyclohydroxybutane
CH3 O (4) 2-bromo-4-chloro-3-ethylcyclobutanol
(4)
NH2 34. The IUPAC name of N compound is
29. What is the correct IUPAC name of the following O
H
compound? (1) N-phenylaminoethanone
H (2) N-phenylethanamide
N (3) N-phenylmethanamide
COOH (4) N-phenylaminomethane
O 35. The correct IUPAC name of
(1) 3-(N-methyl amino) carbonyl propanoic acid F
(2) 3-carboxy (N-methyl) propanamide Br
(3) 4-(N-methyl amino)-4-oxobutanoic acid
(4) 3-(N-methyl carbamoyl) propanoic acid I Cl
1.22 | Organic Chemistry Module I
(1) 1-bromo-2-chloro-6-fluoro-4-iodobenzene (1) 2-methyl-1-(3¢-hydroxy butyl)-6-heptenal
(2) 1-bromo-6-chloro-2-fluoro-4-iodobenzene (2) 9-hydroxy-2-methyl-5-decene
(3) 2-bromo-1-chloro-3-fluoro-5-iodobenzene (3) 1-(3¢-hydroxy butyl)-2-methyl- 6-heptenal
(4) 2-bromo-3-chloro-1-fluoro-5-iodobenzene (4) None of these
O H 39. What is the correct IUPAC name of the compound?
Me Me
Cl
36. IUPAC Name of is:

CN N
H
(1) 4-oxo-2, 6-dimethyl benzene carbonitrile
(2) 4-Cyano-2, 6-dimethyl benzaldehyde (1) 4-chloro-N-ethyl-1-methyl-1-pentanamine
(3) 4-formyl 3,5-dimethyl benzonitrile (2) 5-chloro-N-ethyl-2-hexanamine
(4) None of these (3) 5-chloro-N-ethyl-1-hexanamine
37. What is correct IUPAC name of the compound shown (4) 2-chloro-N-ethyl-5-hexanamine
below? 40. What is the correct IUPAC name of the compound
Cl shown below?
Br
Br OH

(1) 5, 6-dibromo-6-chloro-1, 3-cyclohexadiene


(2) 2, 3-dibromo-2-chloro-1, 4-cyclohexadiene OH CONH2
(3) 1, 2-dibromo-1-chloro-3, 5-cyclohexadiene
(4) 5, 6-dibromo-5-chloro-1, 3-cyclohexadiene
(1) 3, 6-dihydroxy-4-octanamide
38. Write the IUPAC name given
(2) 3, 6-dihydroxy-5-octanenamide
OH (3) 4-hydroxy-2-(1-hydroxy propyl) hexanamide
(4) 3-hydroxy-2-(2-hydroxy butyl) pentanamide


CH = O

Exercise 2

1. The number of sp2–sp2 sigma bonds in the compound NO2


given molecule below is:
(2)
Cl
(1) 1 (2) 3 CH3
(3) 4 (4) 5 4-Methyl-5-chloronitro benzene
2. In compound HC∫C–CH2– CH=CH–CH3 the C2–C3
bond is the type of–
(1) sp–sp2 (2) sp3–sp3 (3)
(3) sp–sp3 (4) sp2–sp2
3. Which of the following is correctly named? 1-Ethyl-3,3-dimethyl cyclohexene
Cl
(1)
(4)
O 2N NO2
4-Chloro-1,3-dinitro benzene 1-Ethyl-3,3-dimethyl cyclohexene
Classification and Nomenclature |   1.23
O (3) 2-cyclobutyl-2-methyl butane
4. IUPAC name of Me is: (4) 1-(1-methylbutyl) cyclobutane
Me 8. What is the systematic IUPAC name of the following
(1) 2-Ethyl-3-methyl epoxy butane compound?
(2) 4-Ethyl-4-methyl oxetane CH3
(3) 2-Ethyl-2-methyl oxetane
(4) 2-methyl-2-ethyl oxetane
5. The correct structure of compound 3, 6-diisopropyl-
2,6-dimethyl nonane is
(1) 8-methyl bicyclo [3, 2, 1] oct-3-ene
H3C H3C CH3 (2) 8-methyl bicyclo [3, 2, 1] oct-2-ene
CH3 (3) 6-methyl bicyclo [3, 2, 1] oct-2- ene
(1) H3C
CH3 (4) 6-methyl bicyclo [1, 2, 3] oct-2-ene
CH3 CH
3 9. According to IUPAC convention, name of the follow-
ing compound is
H 3C CH3
H 3C CH3 CH3
(2) H3C CH3
CH3
CH3
CH3
(1) 2-ethyl-4-methyl-1-cyclopentyl cyclopentane
CH3 (2) 2-ethyl-1-methyl-4-cyclopentyl cyclopentane
CH3
(3) H3C (3) 1-cyclopentyl-3-ethyl-4- methyl cyclopentane
(4) 4-cyclopentyl-1-ethyl-2- methyl cyclopentane
H3C CH3H3C CH3
10. The correct IUPAC name of given substance is

H3C CH3
CH3 (CH3)3C
(4) H3C CH3
(CH3)2CH
H 3C CH3 CH3
(1) 1-isopropyl-2-ter-butyl cyclopentane
6. According to IUPAC convention, what is the name (2) 1-ter-butyl-2-isopropyl cyclopentane
to the compound given below? (3) 2-isopropyl-1-ter-butyl cyclopentane
Me (4) 2-ter-butyl-1-isopropyl cyclopentane
Me 11. According to IUPAC convention, the systematic name
of the compound given below is
Me
Cl
(1) 1-ethyl-5-methyl-4-propyl cyclohexene
Br
(2) 2-ethyl-4-methyl-5-propyl cyclohexene
(3) 5-ethyl-1-methyl-2-propyl-4-cyclohexene F
(4) 4-ethyl-2-methyl-1-propyl-4-cyclohexene (1) 1-(3-chlorocyclohexyl)-4-(4-bromocyclohexyl)-2
7. According to IUPAC convention, the correct name of -fluorocyclohexane
the following compounds is (2) 5-(4-bromocyclohexyl)-2-(3-chlorocyclohexyl)-1
CH3 -flouorocyclohexane
CH3 (3) 4-(4-bromocyclohexyl)-1-(3-chlorocyclohexyl)-2
-fluorocyclohexane
CH3
(4) 1-(4-bromocyclohexyl)-4-(3-chlorocyclohexyl)-
3-fluorocyclohexane
(1) 1-(1, 1-dimethylpropyl) cyclobutane 12. What is the correct IUPAC name of the compound
(2) 1-cyclobutyl-1, 1-dimethyl propane shown below?
1.24 | Organic Chemistry Module I
CH3 16. What is the correct IUPAC name of the compound
H3C shown below?
CH3

H 3C CH3
H 3C
CH3 Cl
CH3

(1) 4-butyl-2, 3 6, 7-tetramethyl-5-propyl octane (1) 4-butyl-6-chloro-3, 5, 6-trimethyl-1-heptyne


(2) 4, 5-bis (1, 2-dimethyl propyl) nonane (2) 4-butyl-6-chloro-3, 5, 6, 6-tetramethyl-1-hep-
tyne
(3) 5-(1, 2-dimethy lsopropyl)-2, 3-dimethyl-4-pro-
pyl nonane (3) 4-butyl-2-chloro-2, 3, 5-trimethyl-6-heptyne
(4) Both ‘2’ and ‘3’ are correct (4) 4-(2-chloro-1, 2-dimethylpropyl)-3methyl-1-
octyne
13. What is the correct IUPAC name of the compound
shown below? 17. What is the correct IUPAC name of the following
compound?

Br Cl
(1)Bis (cyclopentenyl) cyclobutadiene
(2)1, 3-bis (3-cyclopentenyl) cyclobutadiene (1) 1-(2-bromo-4-chlorophenyl)-3-phenyl propane
(3)Dicyclopentene cyclobutadiene (2) 3-bromo-2-(3-phenylpropyl) chlorobenzene
(4)4-[3-(3-cyclopentenyl)-1, 3-cyclobutadienyl] (3) 1-bromo-5-chloro-2-(3-phenylpropyl) benzene
cyclopentene (4) 2-bromo-4-chloro-1-(3-phenylpropyl) benzene
14. What is the correct IUPAC name of the compound 18. What is the correct IUPAC name of the compound
shown below? given below?
C CH CH = O
Cl Cl
Cl C Cl

CH = CH2 Cl Br
Br
(1) 3, 3-bis-(chlorocyclohexyl) 1-penten-4-yne
(2) bis-(4-chlorocyclohexyl) 4-penten-1-yne (1) 3, 4-dibromo-2, 5, 6-trichlorobenzaldehyde
(3) 3, 3-bis-(4-chlorocyclohexyl)-1-penten-4-yne (2) 1, 2-dibromo-3, 5, 6-trichlorobenzaldehyde
(4) 3, 3-bis(4-chlorohexyl)-3-ethynyl prop-1-ene (3) 4, 5-dibromo-3, 3, 6-trichlorobenzaldehyde
15. What is the correct IUPAC name of the compound (4) 5, 6-dibromo-1, 2, 4-trichlorobenzaldehyde
shown below? 19. The IUPAC name of the compound shown below
is
Cl

Br
(1) 5-bromo-2-chloro-1-cyclobutyl-6-cyclohexyl-1,
6-dimethyl-3-hexyne (1) 2, 4,4-timethyl-3-(3,4-dinethyl pentyl) hept-2-
ene
(2) 6-bromo-3-chloro-2-cyclobutyl-7-cyclohexyl-4-
octyne (2) 2-isopropyl-6, 6-dimethyl 5-(methyl ethenyl)
nonane
(3) 3-bromo-6-chloro-7-cyclohutyl-2-cyclohexyl-4-
octyne (3) 2-(methyl ethyl)-5-isopropylidene-6, 6-dimethyl
nonane
(4) 5-bromo-2-chloro-1-cyclobutyl-6-cyclohexyl-1-
methyl-3-heptyne (4) 2, 6, 7-trimethyl-3-(1¢, 1¢-dimethyl butyl) oct-2-
ene
Classification and Nomenclature |   1.25
20. What is the correct IUPAC name of the compound 24. What is IUPAC name of the compound given
shown below? below?
Br CONH–CH3 NH2
O
HO
(1) 4-aminocarbonyl-3-bromo N-methyl phenol
(2) 3-bromo-4-hydroxy N-methyl benzene carbox-
COOH
amide
(3) 5 - b r o m o - 4 - hy d r o x y N - m e t hy l b e n z e n e (1) 4-carboxy-2-(2¢-methyl propoxy) aniline
carboxamide (2) 4-amino-5-(2¢-methyl propoxy) benzoic acid
(4) N-methyl 4-amido-3-bromophenol (3) 4-amino-3- (2¢-methyl propoxy) benzoic acid
21. Which of the following is correct structure of 3, (4) 4-amino-3-(2¢-methyl propoxy) carboxy
3-dibromo-2-chlorobutyl 2-methyl propanoate? benzene
Br O 25. The correct IUPAC name of the compound given
(1) below is
O
Br Br
Cl
Cl Br O
(2) O
O CH3
Br
O CH3
Br
(1) 5-bromo-2-methyl phenyl ethanoate
(3) O
(2) 3-bromo-6-methyl phenyl ethanoate
Br
O Cl (3) 4-bromo-2-{oxy-(1-oxoethyl)} toluene
Br (4) Methyl 5-bromo-2-methyl benzoate
(4) O 26. What is the correct IUPAC name of the compound
Br shown below?
O Cl
22. Which is the correct structure of 2-(2-cyclohexenyl) O
cyclopropanol? C–O–CH2–CH2–COOH
(1) OH (2)
HO (1) 3-carboxy phenyl propanoic acid
(2) 3-(benzoyloxy) propanoic acid
OH (3) 3-hydroxy-3-oxoethyl benzoate
(3) (4) (4) 3-oxyphenyl carboxy propanoic acid
OH
HO
27. The correct structure of 5-(2-chlorobutoxy) pentanoyl
23. What is the correct IUPAC name of the compound chloride is
given below? O

O (1) O Cl
CH3
C2H5O Cl
OC2H5
Cl
O Br Cl O
(2)
(1) 3-bromo-4-chloro-4-methyl ethyl hexanedioate
O Cl
(2) D i e t h y l 4-bromo-3-chloro-3-methyl
hexanedioate O
(3) Ethyl 4-bromo-3-chloro-3-methyl hexanedioate
(3) O
(4) D i e t h y l 3-bromo-4-chloro-4-methyl Cl
hexanedioate Cl
1.26 | Organic Chemistry Module I
O 32. What is the correct IUPAC name of the compound
shown below?
(4) O Cl
Cl
28. The correct structural formula of 1,2-diethyl-1, 8-di-
methyl-5-propyl cyclooctane is
Br
(1) (2) (1) 3-bromo-1-cyclobutyl-5-cyclopropyl benzene
(2) 3-bromo-1-cyclopropyl-5-cyclobutyl benzene
(3) 1-bromo-5-cyclobutyl-3-cyclopropyl benzene
(4) 1-bromo-3-cyclobutyl-5-cyclopropyl benzene
(3) (4)
33. What is the correct IUPAC name of the following
compound?
29. The correct IUPAC name of the compound shown
below is N
Cl
Cl O
CH3
CN

(1) 3-(2-cyanopropyl)-N-ethyl N-methyl pentana-


Br
mide
(1) 1-bromo-2-(1, 2-dichloropropyl) cyclopropane
(2) N-ethyl-3-(2-cyanopropyl) N-methyl pentana-
(2) 2-bromo-1-(1, 2-dichloropropyl) cyclopropane mide
(3) 1-bromocyclopropyl-1, 2-dichloro propane (3) N, 3-diethyl-5-cyano N-methyl hexanamide
(4) 1-(2-bromocyclopropyl)-1, 2-dichloropropane (4) 5-cyano-N, 3-diethyl N-methyl hexanamide
30. What is the IUPAC name of the compound shown 34. What is the correct IUPAC name of the compound
below? shown below?

Br

OH CN
(1) Tetracyclopropyl cyclopropane
(2) Pentacyclopropane (1) 3-bromo-5-(3¢-cyanophenyl) phenol
(3) 1, 2, 2, 3-tetracyclopropyl cyclopropane (2) 5-bromo-3-(3¢-cyanophenyl) phenol
(4) 1, 1, 2, 3-tetracyclopropyl cyclopropane (3) 3-(3¢-hydroxy-5¢-bromophenyl) benzonitrile
31. What is the correct IUPAC name of the compound (4) 3-(3¢-bromo-5¢-hydroxy phenyl) benzonitrile
shown below? 35. What is the correct IUPAC name of the given
compound?

O O
Cl
Cl Cl C C Cl
Cl
OH
(1) 1, 1, 2-trichloro-4-cyclobutenyl cyclohexane
(1) 2-hydroxy-1, 4-benzene dicarbonyl chloride
(2) 3-trichlorocyclohexyl cyclobutene
(2) 2, 4-dichloro carbonyl phenol
(3) 3-(3, 4, 4-trichlorocyclohexyl) cyclobutene
(3) 3-hydroxy-1, 4-benzene dicarbonyl chloride
(4) 3, 4, 4-trichloro-1-cyclobutenyl cyclohexane
(4) 1, 4-dicarbonyl chloride-3-hydroxy benzene
Classification and Nomenclature |   1.27
36. In the IUPAC name of the following compound, there (1) Bicyclo [2,3,2] non-2-ene-6-carbaldehyde
is something wrong. Find the mistake. (2) Bicyclo [3,2,2] non-5-ene-2-carbaldehyde
H (3) Bicyclo [3,2,2] non-2-ene-6-carbaldehyde
O
N (4) Bicyclo [3,2,0] non-2-ene-6-carbaldehyde
39. What is the correct IUPAC name of the compound
O shown below?

N-ethyl-6-oxo-5 propyl heptanamide

(1)Principal functional group is incorrectly chosen


(2)Incorrect prefix for locant is used O
(3)Parent chain is incorrectly selected
(4)Locants name is not written is order of priority (1) 6-oxa spiro [2,3] octane
recommended by IUPAC (2) 6-oxa spiro [4,3] octane
37. IUPAC name of the following compound is: (3) 6-oxa spiro [3,3] heptane
(4) 6-oxa spiro [3,4] octane
40. What is the correct IUPAC name of the following
COOH compound?
OH
(1) 1-hydroxy spiro [3, 4] oct-2-ene-6-carboxylic CH3
acid
(2) 6-carboxy spiro [3, 4] oct-2-ene-1-ol
(3) 3-hydroxy spiro [3,4] oct-1-ene-6-carboxylic
acid
(4) 2-carboxy spiro [3,4] oct-7-ene-6-ol
(1) 3, 5-diethenyl toluene
38. The IUPAC name of the following compound is:
(2) 1, 3-diethenyl-5-methyl benzene
(3) 3-ethenyl-5-methyl styrene
(4) 1, 3, 5-triethenylmethyl benzene

CH = O

Exercise 3

One and More Than one option correct (4) Locant phenyl group is at fifth position of parent
type question ring
2. What is/are true regarding the compound?
1. The correct statement regarding the given compound
is/are O COOH
OH O
(1) It is a carboxy ester
(2) It is an alkanoyloxy acid
Cl CN (3) Its IUPAC name is 4-carboxy-2-pentyl
butanoate
(1) Suffix of the name would be-ol
(4) Its IUPAC name is 4-butanoyloxy-2-methyl pen-
(2) Suffix of the name would be-nitrile
tanoic acid
(3) Parent ring has two locants besides principal
3. What is/are wrong according to IUPAC convention
functional group
in the following naming?
1.28 | Organic Chemistry Module I
OH OH
CN (2)
HO
(1) Parent chain is incorrectly selected 1,3-diethyl-1,4-butanediol
(2) Parent chain has only three carbons
CN
(3) Its IUPAC name is 1-(1-hydroxycyclohexyl)-1-
methyl ethanenitrile
(3)
(4) Its IUPAC name is 2-(1-hydroxycyclohexyl) OH
propanenitrile
3-hydroxymethyl
4. Which of the following compound(s) and their IUPAC benzonitrile
name is/are wrongly matched?
O
CH2CH3
(4) CH–C–CH3

(1) CH3
CH3
l-ethy-3, 3-dimethyl 1, 1-dicyclopropyl
cyclohexane propanone

CH3 6. Which of the following structures and IUPAC name


are incorrectly matched?
(2)
(1) COOCH3 Methyl cyclohexanoate
CH3
Meta-dimethyl Cl O
benzene
(2) NH2 4-bromo-3-
CH3 Br chlorohexanamide
(3)
CN (3) O 2-ethoxy pentane
NC
2-cyclopropyl-2-methyl
propane dinitrile (4) 3, 5-nonanedioic acid
COOH COOH
OH
7. If an alkane C10H22 has a quaternary carbon, two
tertiary carbons and six methyl groups, which of the
(4) H C following could be one of its correct IUPAC name?
3
CH3 (1) 1, 2-dimethyl-1-tertiarybutyl butane
3-ethyl-5-methyl phenol (2) 3-ethyl-2, 2, 4-trimethyl pentane
(3) 2, 2, 3, 4-tetramethyl hexane
5. Which of the following compounds and their names (4) 2, 3, 4, 5-tetramethyl hexane
are correctly matched?
Statement Type Question
CHO
(1) If both Statement-I and Statement-II are correct
(1) COOH and Statement-II is the correct explanation for
Statement-I
4-formyl pentanoic acid
(2) If both Statement-I and Statement-II are correct
and Statement-II is not the correct explanation
for Statement-I
Classification and Nomenclature |   1.29
(3) If Statement-I is correct and Statement-II is COOH
incorrect
(4) If Statement-I is incorrect and Statement-II is
correct
8. Statement-I: The IUPAC name of citric acid is 2-hy- Cl
droxy-propane-1, 2, 3-tricarboxylic acid.
Statement-II: COOH is the principal functional
COOH group of compound which determines the suffix
name.
HOOC COOH
14. Statement-I: IUPAC name of the following com-
OH pound is oct-2-en-5-ynedioic acid
citric acid
HOOC
Statement-II: When an unbranched C atom is COOH
directly linked to more than two like-functional
groups, then it is named as a derivative of the par- Statement-II: Double bond has preference over tri-
ent alkane which does not include the C atoms of ple bond.
the functional group.
15. Statement-I: IUPAC name of the following com-
9. S t a t e m e n t - I : T h e I U PAC name of pound is 2-ethyl-3, 3-dimethyl oxirane.
CH3–CH=CH–C∫C–H is pent-3-en-1-yne and not
pent-2-en-4-yne.
O
Statement-II: Lowest locant rule for multiple bond
is preferred. H 3C
10. Statement-I: The IUPAC name for CH3
H3C
CH3–CH2–CH–CH2—CH–CH2–CH3
Statement-II: In oxirane, numbering starts from oxy-
CH–CH3 Cl gen atom of the ring.
CH3
Comprehension type question
Is 5-chloro-3-ethyl-2-methyl heptane and not 3-chlo- Passage #1 Q. 16–18
ro-5-isopropyl heptane. An aromatic compound has one cyanide and two chloride
Statement-II: The parent carbon chain should con- groups on benzene ring. In IUPAC system, cyanide has
tain larger number of alkyl substituents. higher priority than chloride group, therefore determine suf-
fix of parent name of the compound.
11. Statement-I: IUPAC name of the compound given
below is 4-bromo-3-cyanobenzoic acid 16. How many different IUPAC names can be assigned
to the above mentioned compound?
Br (1) 2 (2) 3
(3) 4 (4) 6
NC 17. What is IUPAC name of the compound above which
COOH
is most polar?
Statement-II: –COOH has higher priority than a (1) 2, 3-dichlorobenzonitrile
cyanide group. (2) 2, 4-dichlorobenzonitrile
12. Statement-I: Dimethyl benzene can have three dif- (3) 2, 6-dichlorobenzonitrile
ferent IUPAC names (4) 3, 4-dichlorobenzonitrile
Statement-II: All three different names are for three 18. Which is IUPAC name of the compound above which
positional isomers. is least polar?
13. Statement-I: Following compound has its IUPAC (1) 2, 3-dichlorobenzonitrile
name 3-chlorocyclopentanoic acid (2) 2, 5-dichlorobenzonitrile
1.30 | Organic Chemistry Module I
(3) 3, 4-dichlorobenzonitrile Code
(4) 3, 5-dichlorobenzonitrile A B C D
(1) P Q R S
Column matching type question (2) P,S Q,R P,S Q,R
19. Match the column. (Matrix): (3) P,Q R,S P,R Q,S
Column-I Column-II (4) P,R PS Q,R R,S
Compounds Number of Benzylic 21.
hydrogen Column-I Column-II
(A) (P) Name end with
suffix ‘anoic acid’
(A) (P) 2 OH COOH
(B) (Q) Name end with
suffix ‘carboxylic
CN acid’
O
CH3
CH2–CH3 (C) CN (R) Name end with
(B) (Q) 3 suffix ‘nitrile’

CH3 OHC
(D) COOH (S) Parent chain/ring
has six carbon
(C) (R) 4 atoms
NC

Code
(D) (S) 5 A B C D
(1) P R,S R,S Q,S
(2) Q R,S R,S Q,S
Code
(3) R Q,S P,R R,S
A B C D
(4) S P,Q R,S Q,S
(1) S R Q P
22. Match the general formula from Column-I with the
(2) R S P Q class they belong to in Column-II
(3) S P R Q
Column-I Column-II
(4) Q R S P
20. Match the IUPAC names from column-I with their
features from column-II. There may be more than (A) (P) has tertiary N-atom
one match for the quantity from Column-I with the N
quantities from Column-II
Column-I Column-II
(A) 3, 3, 4, 4-tetramethyl- (P) has only three car- (B) (Q) has tertiary carbon
1-pentyne bon collinear CN CN
atom
(B) 2-butyne (Q) has four carbon
colinear
(C) 1-butyne (R) substitution of H
N
(C) (R) has five carbons in
by Cl gives single the parent chain
O
product
(D) 2, 2, 5, 5-tetramethyl- (S) substitution of O
3-hexyne H by Cl gives Cl
three different (D) (S) has six carbons in
products (excluding the parent chain
stereoisomers) O Cl
Classification and Nomenclature |   1.31
Code the numbers representing positions of three halide
A B C D locants?
(1) P,R,S P,R Q S Cl Br
(2) Q P,R,S P,S Q,S
(3) P,Q,S Q,R P,R Q Cl
(4) Q,SP, R S P 26. In the compound 7-ethyl 3-nonene-2, 5, 8-tricarbox-
ylic acid, how many atoms are in sp2-hybridisation
Single digit integer type question state?
23. Total number of a-hydrogen in the given following 27. In 3-formy-2-methyl benzoic acid, what is the maxi-
compound is: mum number of hydrogen atoms which may lies in
one single plane?
28. When name of hydrocarbon 3-(1-butenyl)-1, 5-hexa-
diene is rewritten correctly according to IUPAC con-
vention, what would be the number of carbon atoms
in the parent chain.
29. When the following compound is named correctly
according to IUPAC convention, what would be the
24. How many carbon atom present in the parent chain sum of position of two chlorine atoms?
in the given following compound?
O O
Cl
CH3
O Cl
25. If the following compound is correctly named accord- 30. How many secondary hydrogens are present in the
ing to IUPAC convention what would be sum of alkyne named 3-ethyl-4-octyne?

Exercise 4

1. Which of the following compounds has incorrect (3) Isopropylmethyl ketone


IUPAC name: [AIEEE-2002] (4) 2-Methyl-3-butanone
(1) CH2–CH2–CH2–C–O–CH2–CH3 3. The IUPAC name of the compound is
[AIEEE-2004]
O
ethyl butanoate
(2) CH3–CH–C–CH CH3 HO
CH3 O CH3 (1) 3,3-Dimethyl-1-hydroxy cyclohexane
(2) 1,1-Dimethyl-3-hydroxy cyclohexane
2,4-dimethyl-3-pentanone
(3) 3,3-Dimethyl-1-cyclohexanol
CH3 (4) 1,1-Dimethyl-3-cyclohexanol
4. The IUPAC name of the compound shown below is
(3) H3C–CH–CH–CH3 2-methyl-3-butanol
[AIEEE-2006]
OH
Cl
(4) CH3–CH2–CH2–CHO butanal

2. The IUAPC name of CH3COCH(CH3)2 is


[AIEEE-2003] Br
(1) 4-Methylisopropyl ketone (1) 6-Bromo-2-chlorocyclohexene
(2) 3-Methyl-2-butanone (2) 3-Bromko-1-chlorocyclohexene
1.32 | Organic Chemistry Module I
(3) 1-Bromo-3-chlorocyclohexene (1) 1, 2-Epoxy propane (2) Propylene oxide
(4) 2-Bromo-6-chlorocycohex-1-ene (3) 1, 2-Oxo propane (4) 1, 2-Propoxide
5. The IUPAC name of is- [AIEEE-2007] 9. The correct IUPAC name of the following compound

is [JEE Main Online-2014]

(1) 4-methyl-3-ethylhexane
(1) 1, 1-Diethyl-2-dimethylpentane
(2) 3-ethyl-4-methylhexane
(2) 4, 4-Dimethyl-5, 5-diethylpentane
(3) 3,4-ethylemethylhexane
(3) 5, 5-Diethyl-4, 4-dimethylpentane
(4) 4-ethyl-3-methylhexane
(4) 3-Ethyl-4, 4 dimethylheptane
10. The IUAPC name of the given compound is:
6. The correct decreasing order of priority for the func-
[IIT-2006]
tional groups of organic compounds in the IUPAC O
system of nomenclature is [JEE Main-2008]
(1) –SO3H, –COOH, –CONH2, –CHO C6H5–C–Cl
(2) –CHO, –COOH, –SO3H, –CONH2 (1) Benzoylchloride
(3) –CONH2, –CHO, –SO3H, –COOH (2) Benzenecarbonylchloride
(4) –COOH, –SO3H, –CONH2, –CHO (3) Chlorophenyl ketone
7. The IUPAC name of neopentane is (4) Phenylchloroketone
[JEE Main-2009] 11. The IUPAC name of the following compound is-
(1) 2-methylbutane [IIT-2009]
(2) 2,2-dimethylpropane OH
(3) 2-methylpropane
(4) 2,2-dimethylbutane
O CN
Br
8. The IUPAC name of the compound H2O CH–CH3 (1) 4-Bromo-3-cyanophenol
is : (2) 2-Bromo-5-hydroxybenzonitrile
[JEE Main Online-2012] (3) 2-Cyano-4-hydroxybromobenzene
(4) 6-Bromo-3-hydroxybenzontrile

Answer Key

Exercise # 1 Exercise # 2
1. (4) 2. (1) 3. (3) 4. (1) 5. (3) 1. (3) 2. (3) 3. (3) 4. (3) 5. (2)
6. (1) 7. (2) 8. (2) 9. (1) 10. (4) 6. (1) 7. (3) 8. (2) 9. (4) 10. (1)
11. (1) 12. (3) 13. (3) 14. (1) 15. (1) 11. (3) 12. (3) 13. (2) 14. (3) 15. (2)
16. (4) 17. (2) 18. (3) 19. (2) 20. (3) 16. (4) 17. (4) 18. (1) 19. (4) 20. (2)
21. (3) 22. (2) 23. (4) 24. (4) 25. (1) 21. (2) 22. (2) 23. (2) 24. (3) 25. (1)
26. (2) 27. (4) 28. (4) 29. (4) 30. (1) 26. (2) 27. (1) 28. (4) 29. (4) 30. (4)
31. (4) 32. (1) 33. (4) 34. (2) 35. (3) 31. (3) 32. (1) 33. (4) 34. (4) 35. (1)
36. (3) 37. (4) 38. (3) 39. (2) 40. (3) 36. (3) 37. (3) 38. (3) 39. (4) 40. (2)
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north. This town is the sansan, or gathering place for their armies,
and is mostly inhabited by the slaves of the great in Soccatoo, who
have all houses here, and their slaves, who are employed in raising
grain, and tending the cattle, mostly reside here, and in the villages
around. The swampy plain, the river, and the lakes, extend about six
miles to the westward, below Magaria; and from its situation in the
gap of the hills must be very unhealthy, from the north-east winds
driving the vapours right through the town, which, in fact, is situated
on the borders of the swamp.
Morning clear. At 7 left Magaria, the Gadado and sultan having
sent to me the evening before, to say, if I wished to go to Soccatoo
and remain there, until they joined me, I might do so; as they
intended to stay for some days in Magaria, to see if the enemy was
disposed to make an attack on them. I availed myself of this
permission; indeed I had met with nothing but losses and difficulties
since I had joined the Fellata army. I therefore set out, and passed
over a fertile country. Every spot capable of cultivation was planted
with millet and dourra, which was in fine condition. In this district,
they had a scarcity last year, and the year before, and many of the
people had perished for want.
After crossing the hills, which were composed of loose pieces of
iron clay-stone, covered with sand, to the depth of a foot, I arrived at
the river which runs close to the foot of the ridge or hill on which
Soccatoo stands. The banks were crowded with people fishing. Their
nets were formed like a bag, having a border of two small wands,
which they held on each hand, to open the bag. The fish they caught
were small white ones, which are usually carried to the market fried
in butter, and sold at two cowries a-piece.
At 3 I entered Soccatoo, and took possession of the same house I
formerly inhabited; the Gadado having sent a messenger before me,
to make every thing ready for my reception, and to provide for all my
wants.
FOOTNOTES:

[1]It does not appear that he ever recovered them—hence the


hiatus in the journal.
CHAPTER VI.

RESIDENCE AT SOCCATOO, TILL THE DEATH OF THE AUTHOR.

Shortly after my arrival at Soccatoo, I was visited by all the


Arabs of the place, who began to pay me a great many compliments,
and after that, to beg every thing they saw in my possession. They
immediately recollected my servant, Mahomed El Siekis, who was
formerly a slave of Bukhaloom, and the only one of his army who
brought off the flag of the bashaw of Tripoli, at the battle with the
Fellatas at Musfeia; and the same man who restored Major Denham
his horse, when he thought he had lost it in that action. I had found
this man a slave to a Fellata, in the town of Korfu, and bought him for
25,700 cowries, and gave him his liberty. These villains of Arabs now
advised him to leave me, because I was a Christian; telling him that
they would maintain him. I told him he was at full liberty to go, when
and where he pleased; that he was now free, and no longer a slave:
but I advised him not to go away like a thief and abscond, but to
leave me boldly and openly; at the same time I desired him only to
look at the dirty and ragged tobes of his advisers, poor rascals, who
were not able to buy soap to wash themselves or keep their clothes
clean, still less to give him food, wages, and clothes as I did.
On taking a survey of Soccatoo, I was not able to see much, if
any, alteration in its buildings, though I understand it was nearly
consumed by fire last winter, said to be the work of the rebels of
Goobur; who, as the morning breezes at day-break come strong
from the north-east, set fire to one house in that quarter, which
spread rapidly, and consumed nearly two-thirds of the town before it
could be stopped. It is now rebuilt just as it was before. There are at
present eleven gates into Soccatoo; seven having been built up
since the breaking out of the rebellion.
There are ten cadies or judges, who, with old Ben Gumso, an
Arab living here, whenever the sultan leaves the city, keep watch at
the gates day and night, with their people, until his return. Each
takes a gate, and has a temporary house of matting, built close
inside to live in. Ben Gumso, on my arrival, sent to tell me where he
was stationed, and that he could not come and see me, until the
sultan should return, as the punishment for leaving his post would be
death. I accordingly went to see him. He was standing at the door of
his house; he had seven crazy Arab muskets, some of them without
flint or ramrod; but, notwithstanding all this, his post, on account of
the muskets, was considered impregnable.
Tuesday, 24th.—In the afternoon a messenger arrived from the
sultan and the Gadado, to inform me that, as the rebels were daily
expected near Magaria, they did not know when they would be able
to return to Soccatoo. They therefore wished me to return to that
place, and remain with them, and sent two camels to carry my
baggage, and a horse for myself. The report here is, that the
inhabitants of the neighbouring villages near Magaria have all fled,
and taken up their quarters there.
Wednesday, 25th.—I did not start for Magaria to-day, as I had to
lay in a stock of rice, bread, dried meat, and flour, as these articles
are much dearer in Magaria, and bread not known. Magaria is in the
province of Adir, which is also called Tadela, containing a great
number of towns. The inhabitants are for the greatest part negroes.
The rest are a half breed between the Tuarics and their slaves. The
country is full of low rocky hills, and is well watered by lakes and
streams.
Thursday, 26th.—Morning cool and clear. At 8 A.M. I left Soccatoo
for Magaria. I was ill with a severe cold, caught by my own
carelessness, in throwing off my cloth trousers and worsted
stockings on my arrival at Soccatoo. The sun being very hot, I was
quite feverish. I halted at a village till 3 P.M., when I started again,
and arrived at Magaria at 6 P.M., where a house had been prepared
for me. I had messages from the sultan and Gadado, to inquire after
my health. My spleen was considerably increased in one day; but I
went to bed without tasting food: had a fire made at my bed-side,
which procured me a good sweat, and I soon found myself better;
though not lessening the swelling in my side, it eased the pain, as
also the pain in my head and bones.
Friday, 27th.—Cool and clear. I found myself much relieved; and
the Gadado, paying me an early visit, said, if I was able, the sultan
would receive his majesty’s letters and presents. I immediately
dressed in my uniform, and the presents being ready packed in
separate parcels, the time-piece, watch, &c. taken out of the tin
cases, and all just as they had left the maker’s hands, I went,
accompanied by the Gadado, my servants and the servants of the
Gadado carrying the presents, consisting of red silk umbrella, silver
mounted; a message cane, silver mounted; twelve yards red
damask; twelve yards sky blue; twelve yards red silk; twelve yards
blue silk; twenty-four yards cambric; two pounds cloves; a fowling-
piece, brass mountings, single barrel; a plain fowling-piece, double
barrel; a pair of pistols for his eldest son; two short swords; two
boxes of rockets; a quantity of powder, balls, flints, and small shot;
one ream of English foolscap paper; two bundles of black lead
pencils; coloured prints of the royal family, battles, and a plain journal
book; a small ditto; a dozen pair white cotton stockings; a dozen pair
white cotton gloves; a time-piece by Rigby; gold watch by ditto; a
Bramah pen; a pistol, detonating lock; two gilt chains; four clasp
knives; a dressing-case complete; a magnifying looking-glass; two
English bridles; a quantity of medicines; two empty trunks; the New
Testament in Arabic; that part of the Old Testament which was
translated; the Koran in Arabic; Euclid’s Elements in ditto; Ebn
Senna in ditto; History of the Tartars under Tamerlane; Psalms of
David; several chapters of the Bible, with a number of other books in
Arabic. To the Gadado a smaller collection of the same kind of
articles.
Saturday, 28th.—I was visited this morning by Sidi Sheik, Bello’s
doctor, and one of his secretaries, who said he had a message from
the sultan for me, which, on his delivery, certainly surprised me not a
little, though I was cautious not to show him that I considered it as
any thing but a thing of course. It was this, that the sultan had sent
him to inform me that, by whatever road I might choose to return to
England, he would send me, were it even by Bornou, if I should
prefer that road; but that I should consider well before I decided upon
that road, as he had to inform me that, when I was here two years
ago, the Sheik of Bornou had written to him, advising him to put me
to death; as, if the English should meet with too great
encouragement, they would come into Soudan, one after another,
until they got strong enough to seize on the country, and dispossess
him, as they had done with regard to India, which they had wrested
from the hands of the Mahometans: that Bello, however, had said, in
reply, it would be a most disgraceful thing in him to cause an
unprotected man to be put to death, and could only account for such
conduct, on the part of the Sheik, after he himself had placed me
under Bello’s protection, to seek a quarrel between him and the
Sultan Bello.
I observed to Sidi Sheik, that it was certainly very extraordinary to
me, that the Sheik El Kanemi should have written in such a manner;
as he had ever behaved to me with the greatest kindness, both
before I came to Soudan and on my return; and that, when I left
Bornou for England, he had dismissed me with a handsome present,
and the strongest expressions of friendship and regard. I added, that
I must insist on seeing this extraordinary letter, and have a copy of it;
but he said that Bello had sent the letter to Gondo, to his cousin
Abdallah. I must positively see it, I rejoined; and also be allowed to
take a copy of it before I leave this place; for I had a letter and
presents from the king of England for the Sheik. I then asked him
what other path the sultan proposed. He replied that he would place
me under the protection of a maraboot, or holy man, who would
safely conduct me to the sultan of Borgoo, and from thence I might
pass to the northward, as far as the borders of the desert, and
proceed along it until I came near to Foutoo Tora, from whence I
could turn to the southward into a country that belonged to Bello, and
which was inhabited by Fellatas, and not far from one of the English
settlements. I told him it was a matter of serious consideration to me,
as I had a sick servant at Kano, who was unable to travel; but, at all
events, I must have the letter the Sheik of Bornou had sent to Bello.
I was very ill all day; but in the afternoon I paid a visit to Atego,
Bello’s brother, and made him a present of a gilt chain and a pair of
scissors, and a few cloves. His house being at some distance, I was
so much fatigued I thought I should not live until the morning.
Sunday, 29th.—Saw the sultan this morning, who was sitting in
the inner apartment of his house, with the Arabic copy of Euclid
before him, which I had given to him as a present. He said that his
family had a copy of Euclid brought by one of their relations, who
had procured it in Mecca; that it was destroyed when part of his
house was burnt down last year; and he observed, that he could not
but feel very much obliged to the king of England for sending him so
valuable a present. After a few general questions, I retired with the
Gadado; and when we arrived at his house, and were seated, I again
expressed my anxious desire that he would give me a copy of the
letter which had been sent from the Sheik of Bornou, as it was of
some importance to me to be guided as to my choice of the road I
was to take on my return home. The Gadado said he was not aware
of any letter having been sent; that it was very wrong in Sidi Sheik to
have told me such a story; said he must have made a mistake; but,
to relieve me from any uneasiness on that score, he would inquire
into the truth, and let me know to-morrow.
Monday, 30th.—I had been so ill all night with the pain in my side
that I had no rest whatever. At noon the Gadado came to say that he
would go with me to the sultan. Though very ill, I went; and we were
immediately shown into the apartment of the sultan, who was
reading: but when we entered, he laid down his book, and began of
his own accord about the letter. He observed, that a letter had
certainly come to him, but not with the Sheik’s signature; that it
appeared, however, the letter had been written, with the Sheik’s
sanction, by that holy man Hadgi Mohamed Bootabli; and that he
was desired to say I was a spy, and that he would not allow me to go
beyond Soccatoo; hinting, at the same time, that it would be better I
should die, as the English had taken possession of all India by first
going there by ones and twos, until we got strong enough to seize
upon the whole country. And thus ended our interview.
Tuesday, 31st.—I was much better this morning, and the swelling
and pain in my side much less, a dose of calomel I took having done
its duty; but I thought it advisable not to stir out all day. The sultan
and Gadado sent to me to know how I was.
Wednesday, Nov. 1st.—Clear. Magaria is now increasing to a
town of considerable size. Before, it was without shape or form; now,
all the people from the villages, for a considerable distance around,
have been ordered to live here; and the houses being properly
arranged, each man’s cluster of huts being fenced round with
matting, nearly all the vacant places are filled up with houses or
enclosures for cattle. A new wall has been built, according to the
present Goobur mode of fortifying a town; which is, to build a low
wall, with a deep ditch outside, and to erect on the wall a stockade of
rough stakes, firmly fixed in an upright posture, through the openings
of which the people inside are enabled to shoot their arrows and fire
muskets, when they have any. This new wall was not quite
completed when I arrived; but as every man having a house in the
town was to bear his part in the work, and every man of
consideration who held office under the sultan was to superintend
that part of it next to his residence, as well as to employ his slaves
and servants in bringing wood and materials, the progress advanced
rapidly.
This evening we had a courier from the nearest town in the
province of Zamfra, bringing intelligence that Aleva, the rebel sultan
of Goobur, had died by an arrow wound in his side, which he
received when we made the attack. Whether this will have any effect
in bringing about a reconciliation with Bello and them I know not.
Thursday, 2d.—Warm, with light flying clouds. The Juma, or place
of worship, in Magaria, is only a temporary one. I have had several
opportunities of seeing them at prayers, being only a square
enclosure of matting, supported by stakes, and open on one side,
which is to the east. The Iman, or priest, a head man, stands at a
little distance in front, on his mat; the rest of the people in rows
behind him. He repeats the prayer, and those behind him also
repeating inwardly at the same time, and with the greatest regularity,
in a kneeling posture, with their heads inclined.
I had a long visit from Prince Atego this morning, who was
amazingly civil: at last it came out that he was afflicted with a
disorder which he represented as being very common in this country.
I recommended him to drink rice water in plenty, to refrain from
pepper and strong spices, and not to visit his ladies too often, and to
wear a hat when he rode out. I also gave him a dose of calomel,
recommending him to use natron in his food.
The henna or salli, with whose leaves they stain their hands and
toes, is made of pounded leaves, mixed with water to the
consistence of a poultice, which is laid on thick, and bound with
gourd leaves to keep it on. To see a person in this state, without
knowing that he was sacrificing comfort to make himself look
beautiful, would be apt to excite pity for the poor man, and to
imagine that he had fallen from some height, and bruised his hands
and feet so badly as to require their being poulticed to reduce the
inflammation. Some great people go so far as to have themselves
stained every three nights.
Friday, 3d.—The negroes and most of the Arabs are great
gamblers, though it is strictly prohibited by the Fellata laws. Their
principal game is called cha-cha, and is played by any number of
persons at a time, with cowries. Night is the usual time for this game;
and so eager are they in it, that they will frequently stake their
breeches and every part of their dress. I should never have known of
its existence, had not one of my servants, named Micama, a native
of Zinder in Bornou, come home last night with the loss of his tobe;
and on my insisting this morning that he should not enter the house
in such a state, he pleaded the heat of the weather, and made other
excuses, which I could not allow: the other servants then told me
what he had been at, and said he was an expert hand, and could not
refrain from playing when he saw others play. I advanced him money
to buy another tobe, telling him if I ever knew him to play again, I
should give him up to the Fellatas, who punish all caught at such a
game with death, or something approaching it. In the afternoon I took
leave of the sultan, who breaks up in the night, and proceeds to
Soccatoo.
Saturday, 4th.—Morning cool and clear. The sultan did not leave
last night, but to-day at 3 P.M. I had to go and see the chronometer
carefully put up to bear carriage without injury: it is considered the
most valuable part of his property, and numbers come from a great
distance to hear it strike. One of the gold watches he has already
spoiled, and I have had to give his brother Atego my silver watch for
it in return, but I have got the worse bargain. If the sultan had not
asked me I should never have done it, as it has the new patent key,
and kept a regular rate from England.
Sunday, 5th.—I did not start this morning, as I had been very
unwell all night: got a new camel, and employed a Tuarick to buy me
another, as they are nearly 2000 cowries cheaper here than they are
at Kano.
Monday, 6th.—Cool and clear. At 6 A.M. left Magaria. I rode my
new camel, as his load was light, and I had no horse. At 11 A.M.
halted at a spring for an hour, and started again at 2. Arrived at
Soccatoo.
Tuesday, 7th.—This day I visited the sultan about noon, and, at
his request, taught a man, one of his servants, how to wind up the
time-piece, which is one of eight days. In the afternoon I was visited
by three Fellatas, Hadji Omer from Foota Tora, Malem Mahomed
from Timbuctoo, and the third from a neighbouring town to
Timbuctoo. Malem Mahomed says the whole of the district called
Timbuctoo is at present under the authority of the Tuaricks; that the
principal town is called Timbuctoo; and that their gold comes from
Ashantee, Gonga, and Bambarra, where they exchange it for salt to
the Tuaricks, and cloths to the inhabitants of Fez, Ghadamis, and
Tripoli; that Timbuctoo produces no gold, it being only the great
market where all the gaffles from the north and east meet those of
the south and west; that few Arabs now come from Fez and
Morocco, owing, he says, to the Arabs, called Waled Dleim, cutting
off the caravans.
Hadji Omar, who was an intelligent man, told me that forty men
arrived at Sego with the late Mungo Park. That, out of the forty,
thirty-five had died of sickness, and that five only embarked in the
canoe given to him by the sultan of Sego. That they were repeatedly
attacked by the Tuaricks, of whom they killed a great number.
Whether any, or how many, of those belonging to the canoe were
killed, he could not say. The Hadji had just returned from Mecca, and
wished to go there again, if he could get an opportunity; but, as he
said the sultan of Baghermi and his subjects had been driven into
the mountains to the south of that kingdom by the Sheik el Kanemi,
there was no passing through that country, as it was now only
inhabited by wandering Arabs, who plunder all that fall into their
hands, otherwise it was the best road to the east from Adamowa, by
the way of Baghermi.
Friday, 10th.—For the two last days I have found myself very ill,
with an enlargement of the spleen. Soccatoo was built by Sheik
Othman, usually known by the name of Danfodio, or the learned son
of Fodio. He was a good linguist; and knew most of the languages of
the interior, which he spoke fluently, and also all the dialects of the
Arabic. He knew all the learning of the Arabs; and, what was of the
greatest importance to him, was firmly believed to be a prophet; and
the belief continues, getting stronger as the Fellatas get stronger. He
came out of the woods of Ader, or Tadela, and settled, and built a
town in the province of Goobur, where the Fellatas began to gather
around him; he soon began to interfere with the affairs of the sultan
of Goobur, saying this was proper to be done, and such a thing was
improper. This not pleasing either the people of Goobur or the sultan,
he was ordered out of the country, he and his people. This order he
did not obey; and the people of Goobur rose and drove them out;
when he again settled in Ader, not in the woods, as formerly, but built
a town. Fellatas gathering round him from all the different countries,
he divided them under different chiefs, giving each chief a white flag,
telling them to go and conquer in the name of God and the prophet,
as God had given the Fellatas the lands and the riches of all the
Kaffirs, as they, the Fellatas, were the only true believers. In addition
to the white flag, the Fellatas were to wear a white tobe, as an
emblem of their purity, and their war-cry was to be Allahu Akber! or,
God is great! That every one who was wounded, or fell in battle, was
sure to gain paradise. Their belief in him as a prophet, their own
poverty, numbers, and the apparent wealth of the blacks, who had
been lulled into a fatal security, made the latter fall an easy prey to
their conquerors. Kano submitted without a blow. The next was
Goobur; the people of which had taken the alarm, and attempted to
turn Danfodio out of his town in Ader, but they were driven back, and
the wily old chief then attacked them, overran their country, and
killed the sultan. After this the whole of Houssa, with Cubbé, Youri,
and part of Nyffé, fell under their dominion. The whole of the interior,
from east to west, was terror-struck. Bornou, in the east, was
attacked with success, as was also Yourriba, in the west. Here they
found more resistance than any where else, as they (the people of
Yourriba) could not be made to believe in his doctrine or prophecy,
as they were confirmed Kaffers, who, on the invasion of the Fellatas,
put all the Mahometans to death, whether natives, or in caravans
trafficking; quite denying the plea that God had given to the faithful
their lands and houses, and their wives and children to be slaves.
Notwithstanding, they took Rakah, Elora or Affaga, besides a great
number of other towns, reaching to the sea coast, in their
expeditions; and once entered Eyeo, or Katunga, the capital, a great
part of which they burnt down, giving liberty to all the Mahometan
slaves, and encouraging others to kill their pagan masters and join
them. After they had fairly settled themselves, the Arabs from the
east and west came to congratulate Danfodio on his newly acquired
territory. Numbers of his countrymen came from the west to settle in
Houssa. These he located principally in the province of Zegzeg,
where he gave the lands and houses of the negroes who had fled to
the mountains and inaccessible parts of that province lying to the
south. To the Arabs of Tripoli and Fezzan he made large presents of
slaves and camels, sending none away empty-handed. The news of
his fame spread every way. Arabs, in shoals, came and passed with
him as sherifs, and would seldom go away under a hundred slaves,
with camels and provisions.
Before he gathered the Foulahs, or Fellatas, under his
government, they did not live in towns, but were scattered over the
greater part of Soudan, attending to their herds and flocks, living in
temporary huts, generally in the midst of unfrequented woods,
seldom visiting the towns. This business they left to the women, who
attended the markets, and sold the produce of their cattle. The men
were reported to live a religious and harmless life, spending a great
part of their time in reading the Koran and other religious books. Now
and then a few of their learned men would come forth, and engage
themselves for a few years with the Mahometan sultans and
governors, until they had collected a little money, with which they
purchased a few cattle, and then returned to the woods to their
countrymen, who moved about from one province to another,
according to the seasons, and the nature and quantity of pasture and
water; contented with building temporary huts of straw and rushes,
and to be left in peace. No one indeed thought of disturbing them, or
interfering with their pursuits, they being probably considered as too
contemptible and insignificant to excite any fear. Thus dispersed, no
one but themselves knew or could guess at their numbers. Melli, or
the petty kingdoms of Foota-Torra, Foota-Bonda, and Foota-Jella,
were the places from whence they spread themselves eastward,
until they became very considerable, in point of numbers, in all the
countries between the above-mentioned places and Wady. Many of
them had performed their pilgrimage to Mecca, and others had
visited the empires of Turkey and Morocco, as also Algiers, Tunis,
and Tripoli, bringing back with them all the Arabic books they were
able to beg or buy.
In the year of the Hegira 1218, the old Mallem Sheik Othman
Danfodio, Sheik of the Koran, became religiously mad, and is said to
have died some years afterwards in that state. This Foulah or Fellata
conqueror was styled Sheik of the Koran from his being perfect
master of that book, not only being able to read it, and all the
commentaries upon it, but also to repeat any part, and explain it,
from memory. The laws of the Koran were in his time, and indeed
continue to be, so strictly put in force, not only among the Fellatas,
but the negroes and Arabs, and the whole country, when not in a
state of war, was so well regulated, that it was a common saying,
that a woman might travel with a casket of gold upon her head from
one end of the Fellata dominions to the other.
His madness took a very unhappy turn. In the midst of a
paroxysm, he would constantly call out that he should go to hell, for
having put so many good Mussulmen to death. The Arabs used to
take advantage of this, and tell him he was sure to be damned,
unless he made amends by giving them presents to assuage the
manes of their friends. Not so with the Fellatas. These people had so
great a veneration for their chief that, when his head was shaving,
the hairs were carefully collected, and preserved by them in cases of
gold and silver, and they used to come from all parts of the interior to
get a sight of him, negroes as well as Fellatas.
After his death, his son Mohamed Bello, the present sultan,
governed the kingdom which his father had conquered; but that part
of the country to the westward of Houssa he left to his brother’s son,
Mohamed Ben Abdallah, while the eldest, Mohammed Bello, had
Haussa, with all the countries to the south and east. Atego, the
brother of Mohammed Bello, both by father and mother, attempted to
usurp the government of the latter, at the death of the Sheik Othman;
but his brother put him down, and confined him to his house for
twelve months; and they are now as good friends as before.
Bello extended the walls of Soccatoo, which is now the largest
and most populous town in the interior that I have seen. Within these
walls live all the children which Danfodio had by his different wives
and concubines, very quietly and without splendour, except Atego,
who is a mean fellow, but keeps a large establishment. At the death
of Danfodio, in the year of the Hegira 1232 (in 1816 of ours), the
province of the Goobur, Zamfra, part of Kashna, and Zegzeg, threw
off the yoke of the Fellatas, and put the whole of them to death that
they could lay their hands on. Since that time, Bello has retaken the
greater part of Goobur; part of Zamfra, and Guari, the southern part
of Kashna, have made their peace, as also part of Cubbé; but on this
condition, that they shall be ruled by their native chiefs, and the
Fellatas not to interfere with them. Since my arrival, he has also got
back the greater part of Nyffé. Youri has, since 1822, joined in the
rebellion, being forced by the people of Zamfra, who at all times can
command that province, if not supported by Cubbé or Soccatoo. The
governor is to be hereditary, not like most of the other provinces and
kingdoms in the interior, where the oldest relation always succeeds.
The city of Soccatoo stands on the top of a low hill, or rising
ground, having a river passing at a short distance from the northern
wall. It is formed of the united branches of the several streams,
which take their rise to the south of Kashna, and flow past Zirmie.
Having passed Soccatoo, it crosses the district of Cubbé in a south-
westerly direction, and at the distance of four days’ journey enters
the Quorra. It is well stored with fish, which afford the poor people of
Soccatoo a very considerable part of their food. The city is
surrounded by a wall, about twenty-four feet high, and a dry ditch.
The wall is kept in good repair, and there are eleven gates; seven
having been built up at the breaking out of the rebellion. The clay
walls which surround all African towns, clusters of huts, and even
single coozies, give a deadly dull appearance to them all, whether
negro or Mahometan. The only appearance of animation is given by
the great number of slaves and others moving to and fro, or
lounging, or lying in the shade at the doors of great men. A great part
of the town within the walls might be taken for a number of ill-
enclosed gardens.
The house of the sultan is surrounded by a clay wall, about twenty
feet high, having two low tower-like entrances, one on the east, the
other on the west. The eastern one is entirely guarded by eunuchs,
of whom he has a great number, I suppose because the harem is on
the eastern side. The whole of his house forms, as it were, a little
town of itself; for in it there are five square towers, a small mosque, a
great number of huts, and a garden, besides a house, which consists
of one single room, used as the place for his receiving and hearing
complaints, receiving visitors, and giving audiences to strangers.
This room or house is nothing more than what we should call in our
country a shed. Two large pillars support a beam, or bundle of long
rods, plastered over with clay. These support the rafters, which are of
the branches of the palm-tree; on the back part is an imitation of a
fire-place, with a fire-screen before it; and on each side are two
chairs, which are also plastered with clay, and coloured like
mahogany. The ornament or figure on the back of these is the same
as those seen on a number of chairs in England, and corresponds
with that on the fire-screen. The walls are ornamented partly in the
European and partly in the African fashion. There are two doors, one
in the front towards the right, and the other in the left end of the
house, and which leads through a small street of huts to a large hut,
with two doors: passing through and within a few yards of it stands a
large square clay tower, with an entrance in the west side. The
interior of this is common in most of the great men’s houses in
Houssa. It is in the shape of a dome, formed of eight arches
springing from the ground; in the centre of which is a large bright
brass basin, acting as it were in the place of a key-stone to the
arches, which are turned by branches plastered over with clay. If I
had not seen them constructing the arches and pillars of a mosque, I
should have supposed them to be formed entirely of clay, as the
wood in no part appears. The clay serves to keep the white ants
from destroying the wood; they are ornamented in their fashion while
the clay is wet, an operation performed with the fingers and a small
square stick. From the arches, about one-third up, runs a gallery
quite round the interior building, having a railing with pillars of wood,
covered and ornamented with clay. There are three steps leading up
to this gallery, from which every thing in the dome may be seen or
heard. Passages also lead from it into small rooms, having each one
small window, or square hole, some appearing to be used as store-
rooms, and others as sleeping-rooms. The floor of the dome was
covered with clean white sand. The height might be, from the floor to
the brass basin in the centre of the arches, from thirty-five to forty
feet. The air inside of this dome was cool and pleasant; and Bello
told me he often used it as a place to read in during the heat of the
day. These two apartments are the only two I have seen deserving
remark within his enclosure. One night that he sent for me, when it
was rather late, I was led by the hand by an old woman through
several apartments before I arrived at the one in which he was. As
there was no light, I could only judge by the stooping, and ascending
and descending through doors and galleries, that I passed through
some large rooms, out of one into another.
The houses of the other great men, and those of his brothers, are
nearly the same, but on a much smaller scale. A great number of the
poorer sort are fenced round with matting, or the stalk of dourra or
millet. Before the west front of the sultan’s enclosure is a large open
space, of an irregular form, on the west side of which stands the
principal mosque. In this space is also the prison, a building of about
eighty feet long, and nearly the same in breadth, covered at top with
a flat clay roof, overlaid with boughs. Inside is a deep pit, where
those who have committed the greatest crimes are confined. No
person is put in prison for debt; only thieves, prisoners of war (taken
singly), such as spies, and disobedient slaves, who, on a complaint
to the sultan that they will not work, are sent to prison. Their only
food is the bran or husks of millet and dourra, with water; but their
friends are allowed to give them food, if they have any. It is a filthy
place, and the terror of the men-slaves of Soccatoo. The prisoners
are taken out, two and two, every day to work at the walls, or any
laborious work which may occur.
Another house and the tomb of the sultan is further to the west of
the mosque, on the north side of a broad street, which leads to the
western gate. It is occupied by his widows, concubines, and
youngest son, called Abedelgader, who is not arrived at a proper age
to have a house for himself. The sheik’s tent is inside of the square
enclosure, behind the room he generally occupied when living. It is
visited as a holy place by all Mahometan strangers, from which they
afterwards hope to enjoy the good things of this world, and that of
their world to come.
The ordinary occupations of the higher, and indeed I may say of
all classes of the Fellatas is, they rise at day-break, wash and say
their prayers, count their beads for about half an hour, and then
chew a gora nut, if they have any; which done, they sip a quantity of
senkie, or furro-furrocoo. These articles are a preparation of half-
boiled dourra flowers, made into balls of about one pound, mixed up
with dry flour. Senkie is one of these balls, bruised and mixed with
milk; furro-furrocoo is the same kind of ball mixed with water. About
10 A.M. they have rice boiled, which they eat with a little melted
butter. After this they pay visits, or lounge in the shade, hear the
news, say prayers, count their beads, which employ them till sunset,
when they have a meal of pudding, with a little stewed meat and
gravy, or a few small fish; they then retire to rest.
During the spring and harvest the proprietors of estates ride out to
their different slave villages to look after their grain, cotton, indigo,
&c.; or to the place where they have their cattle. The occupations of
the poorer class, who are not engaged in trade, are much the same
as those of their superiors; their food is somewhat different, being
principally confined to furro-furrocoo. The wives of the principal
people, of whom they all appear to keep up the number allowed by
the Koran, which is four, with concubines as many as they can get or
are able to keep, are occupied in directing the female slaves in their
work, cooking their husband’s food, cleaning and spinning cotton,
and dressing their hair, teeth, eye-brows and eye-lashes, which take
up no little time. They also take charge of sending the female slaves
to market to sell their spare cotton, grain, furro-furrocoo, millet, cakes
fried in butter, fried fish, which are usually caught by the younger
male slaves; in receiving or paying visits, for they are great gossips.
They are allowed more liberty than the generality of Mahometan
women.
The dress of the men is a red cap, with a blue tassel of silk, a
white turban, part of which, or a fold, shades the brow and eyes;
another fold is taken over the nose, which covers mouth and chin,
hanging down on the breast; a white shirt, close at the breast and
short in the skirts, a large white tobe, and white trousers, trimmed
with red or green silk, and a pair of sandals or boots: this is the dress
of the greater part of the wealthy inhabitants. When travelling, they
wear, over the turban, a broad-brimmed straw hat, with a round low
crown. Some who do not affect great sanctity or learning wear check
tobes and blue turbans over the forehead, with the end hanging
down behind; the poorer, a white check tobe, white cap and trousers,
and sandals. Some are content with the straw hat only, but all wear a
sword, which is carried over the left shoulder. The women have a
cloth striped with blue, white, and red, falling as low as the ankles;
silver rings in the ear, about an inch and a half in diameter, bracelets
of horn, glass, brass, copper, and silver, according to the quality of
the wearer; round the neck, beads, and strings of glass, or coral;
round the ankles, brass, copper, or silver, and sometimes rings on
the toes as well as fingers. The fashionable ornament is a Spanish
dollar soldered fast to a ring. The poor women have pewter, brass,
and copper rings. The hair is generally turned up like a crest on the
top of the head, with something like a pig’s tail hanging down from
each extremity, a little before the ears.
Some of the Fellata women have the hair frizzed out at the ends,
all round the head; others have the hair plaited in four small plaits,
going round the head like a riband or bandeau. This, and all the
plaited parts, are well smeared over with indigo or shumri. The razor
is applied to smooth all uneven places, and give a high and fine arch
to the forehead; they thin the eye-brows to a fine line, which, with the
eye-lashes, are rubbed over with pounded lead ore, and done by
drawing a small pen that has been dipped in this ore. The teeth are
then dyed with the gora nut, and a root of a shining red colour; the
hands and feet, the toe and finger nails, are stained red with henna.
A lady thus equipped is fit to appear in the best society. The looking-
glass is a circular piece of metal, about an inch and a half in
diameter, set in a small skin box, and is often applied to. The young
girls of the better sort of people dress much in the same manner as
their mothers, after they arrive at the age of nine or ten; before that,
they have very little dress, except the binta or apron, scolloped or
vandyked round with red cloth, with two long broad strings vandyked
round in the same manner, hanging down as low as the heels
behind. This is the dress of the poorer sort of people, until fit for
marriage, as also of a great many of the virgin female slaves.
Their marriages are celebrated without any pomp or noise. The
bride, as far as I was informed, is always consulted by her parents;
but a refusal on her part is unknown. The poorer class of people
make up matters much in the same way; that is, after having got the
consent of one another, they ask their father and mother. The dowry
given by a man of good condition, with regard to riches, may be said
to consist of young female slaves, carved and mounted calabashes
or gourds, filled with millet, dourra and rice, cloths for the loins,
bracelets, and the equipage of her toilet, and one or two large
wooden mortars for beating corn, &c. and stones for grinding, &c.;
even these are carried in procession on the heads of her female
slaves, when she first goes to her husband’s house.
It is said that, in the event of the husband sleeping or having
connexion with any of the female slaves given as dower to the wife,
he must give her in lieu a virgin slave of equal value the next day.
This never causes any dispute between the parties.
Their mode of burial I have never seen; but I understand they
always bury their dead behind the house which the deceased
occupied while living. The following day all the friends and relations
of the deceased visit the head of the family, and sit a while with him
or her. If the husband dies, the widow returns to the house of her
parents, with the property she brought with her.
The domestic slaves are generally well treated. The males who
have arrived at the age of eighteen or nineteen are given a wife, and
sent to live at their villages and farms in the country, where they build
a hut, and until the harvest are fed by their owners. When the time
for cultivating the ground and sowing the seed comes on, the owner
points out what he requires, and what is to be sown on it. The slave
is then allowed to enclose a part for himself and family. The hours of
labour, for his master, are from daylight till mid-day; the remainder of
the day is employed on his own, or in any other way he may think
proper. At the time of harvest, when they cut and tie up the grain,
each slave gets a bundle of the different sorts of grain, about a
bushel of our measure, for himself. The grain on his own ground is
entirely left for his own use, and he may dispose of it as he thinks
proper. At the vacant seasons of the year he must attend to the calls
of his master, whether to accompany him on a journey, or go to war,
if so ordered.
The children of a slave are also slaves, and when able are usually
sent out to attend the goats and sheep, and, at a more advanced
age, the bullocks and larger cattle; they are soon afterwards taken
home to the master’s house, to look after his horse or his domestic
concerns, as long as they remain single. The domestic slaves are
fed the same as the rest of the family, with whom they appear to be
on an equality of footing.
The children of slaves, whether dwelling in the house or on the
farm, are never sold, unless their behaviour is such that, after
repeated punishment, they continue unmanageable, so that the
master is compelled to part with them. The slaves that are sold are
those taken from the enemy, or newly purchased, who, on trial, do
not suit the purchaser. When a male or female slave dies unmarried,
his property goes to the owner. The children of the slaves are

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