SOLVED OBJECTIVE EXAMPLES

EXAMPLE 1
CH3 CH3

H OH HO H

Br H Br H

C2H5 C2 H5

The molecules represented by the above two structures are

(a) identical (b) enantiomers
(c) diastereomers (d) epimers

SOLUTION
Since the two stereoisomers are not mirror image, they are diastereomers.
\ (c)

EXAMPLE 2
Which of the following compound is incapable of exhibiting tautomerism
O O
(a) (b)
O O
(c) O O (d) CH=CH—OH

SOLUTION
Benzoquinone is very stable as it is highly conjugated system so it does not get enolized.
\ (c)

EXAMPLE 3
Benzil on reduction with NaBH4 gives (A). The number of optically active stereoisomers possible
for (A) are
(a) 1 (b) 2
(c) 3 (d) 4

SOLUTION
NaBH * *
PhCCPh

4PhCHCHPh
O O OH OH
The reduction product will have 3 stereoisomers of which only 2 would be optically active. The third
isomer (meso) will be optically inactive.
\ (b)
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 2
EXAMPLE 4
Which of the following species is/are aromatic

(a) (b)

SbCl6
Ph

(c) (d)

 H
Ph

SOLUTION
For a compound to be aromatic, there must be cyclic delocalization with the closed loop formed must
have (4n + 2) p electrons. In the given case, (a), (b) and (c) qualify to be called as aromatic.
\ (a), (b) & (c)

EXAMPLE 5
Which of the following carbocations is expected to be most stable?
CH3 CH3




X H X H
CH3 CH3

 
H H
X X
SOLUTION
Here in the given problem, carbocation (b) is stabilized most, as the CH 3 group is attached to the
carbon bearing positive charge.
\ (b)

EXAMPLE 6
Keto enol isomerism is observed in
O O
(a) (b)
C6H5  C  H C6H5  C  CH3
O CH3
O
(c) (d) C6H5  C  C  C6H5
C6H5  C  C6H5
CH3
SOLUTION
For a compound to exhibit ketoenol isomerism, presence of ahydrogen is necessary. This is
satisfied only by acetophenone.
\ (b)

 STRAIGHT OBJECTIVE TYPE

 O – Level
1. Molecule in which the distance between two adjacent carbon atoms is longest is
(a) ethane (b) ethene
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 3
(c) ethyne (d) benzene

2. Number of pbonds in the following compound CH3C º C  CN

(a) 1 (b) 2
(c) 3 (d) 4
1 2
3. The bond between carbon atoms 1 and 2 in N º C  C H  CH 2 involves the hybridized carbons
(a) sp2 and sp2 (b) sp3 and sp
(c) sp and sp2 (d) sp and sp3

4. The compound in which all carbons use only sp3 hybrid orbitals for bond formation
(a) HCOOH (b) (H2N)2CO
(c) (CH3)3COH (d) (CH3)3CCHO

5. When the hybridization state of carbon atom changes from sp 3 to sp2 and finally to sp, the angle
between the hybridized orbitals
(a) decreases gradually (b) increases progressively
(c) is not affected (d) none of these

6. The ClCCl angle in 1,1,2,2tetrachloroethene and tetrachloromethane respectively will be about

(a) 120° and 109.5° (b) 90° and 109.5°
(c) 109.5° and 90° (d) 109.5° and 120°

7. Number of pelectrons in naphthalene is

(a) 10 (b) 5
(c) 3 (d) 6

8. Number of tertiary carbon atoms in

CH3 H CH3 H
| | | |
HC C C C  CH3
| | | |
CH3 CH3 CH3 CH3
(a) 4 (b) 3
(c) 2 (d) 1

9. The number of isomers for the compound with molecular formula C2BrClFI is
(a) 3 (b) 4
(c) 5 (d) 6

10. Number of structural isomers of C6H14 are

(a) 4 (b) 5
(c) 6 (d) 7
11. The enolic form of acetone contains
(a) 9s bonds, 1p bond and 2 lone pairs (b) 8s bonds, 2p bonds and 2 lone pairs
(c) 9s bonds, 2p bond and 1 lone pair (d) 10s bonds, 1p bond and 1 lone pair

12. The compound which is not isomeric with diethyl ether is

(a) methylpropyl ether (b) butanol
(c) 2methyl2propanol (d) butanone
13. The compound
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 4
H3C H

C=C H
H3C C
H3C COOH
will exhibit
(a) Geometrical isomerism (b) Optical isomerism
(c) Geometrical and optical isomerism (d) Tautomerism
14. In following
COOH COOR COOH
H OH H OH H OH

H OH H OH HO H
COOR COOH COOR
(A) (B) (C)

(a) A and B are identical (b) A and B are enantiomers

(c) A and B are diastereoisomers (d) A and C are enantiomers

15. How many optically active stereoisomers are possible for 2,3butanediol ?
(a) 1 (b) 2
(c) 3 (d) 4

16. The number of enantiomers of the compound CH3CHBrCHBrCOOH is

(a) 0 (b) 1
(c) 3 (d) 4

17. Isomerism between CH3CH2CH2OH and CH3OC2H5 is

(a) chain (b) positional
(c) functional (d) structural

18. The optical isomers which are not mirror images of each other
(a) enantiomers (b) diastereoisomers
(c) tautomers (d) metamers

19. Which has asymmetric carbon atom

Cl Br H Cl
| | | |
(a) HCCH (b) HCCCl
| | | |
H H H H

H Cl H H
| | | |
(c) HCCD (d) HCCH
| | | |
H H Br OH
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 5
20. Which one of the following has the smallest heat of hydrogenation per mole ?
(a) 1butene (b) trans2butene
(c) cis2butene (d) 1, 3butadiene

21. Which of the following compounds will show geometrical isomerism ?

(a) 2butene (b) propene
(c) 1phenylpropene (d) 2methyl2butene

22. The hybridization of carbon atoms in C-C single bond of vinyl acetylene
(CH2 = CH  C º CH) is :
(a) sp3-sp3 (b) sp2-sp
2
(c) sp-sp (d) sp3-sp

23. Isomers which can be interconverted through rotation around a single bond are
(a) conformers (b) diastereoisomers
(c) enantiomers (d) positional isomers

24. Polarization of electrons in acrolein may be written as

d d+ d+ d
(a) CH2=CH-CH=O (b) CH2=CH-CH=O

d d+ d+ d
(c) CH2=CH-CH=O (d) CH2=CH-CH=O
25. Keto - enol tautomerism is observed in
(a) H5C6-CHO (b) H5C6-COO-CH3
(c) H5C6-CO-C6H5 (d) H5C6-CO-CH2-CO-CH3
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 6
 I – Level
1. The compound which has one isopropyl group is :
(a) 2,2,3,3 -tetramethyl pentane (b) 2,2 - dimethyl pentane
(c) 2,2,3 - trimethyl pentane (d) 2-methyl pentane

2. Only two isomeric monochloro (structural isomerism only) derivatives are possible for
(a) n-butane (b) 2,2 - dimethyl pentane
(c) benzene (d) 2-methyl pentane

3. Which is the strongest carboxylic acid among the following ?

(a) Cl3CCO2H (b) Br3CCO2H
(c) F3CCO2H (d) Cl2CHCO2H

4. The compounds C2H5OC2H5 and CH3OCH2CH2CH3 are

(a) enantiomers (b) geometrical isomers
(c) metamers (d) conformational isomers

5. Of the following compounds, which will have a zero dipole moment ?

(a) 1,1 - dichloroethylene (b) cis - 1,2 dichloroethylene
(c) trans - 1,2 - dichloroethylene (d) none of these compounds

6. The compounds :

H3C CH3 H3C H

C=C and C=C
H H H CH3
are examples of :
(a) enantiomers (b) geometrical isomers
(c) metamers (d) optical isomers

7. Which of the following, compounds display geometrical isomerism ?

(a) CH2=CHBr (b) CH2=CBr2
(c) ClCH=CHBr (d) Br2C=CCl2

8. Among the following the compound having the most acidic alpha - hydrogen is :
(a) CH3CHO (b) CH3COCH3
(c) CH3-C-CH2CHO (d) CH3-CO-CH2-CO2CH3
||
O
9. Allyl isocyanide has:
(a) 9 sigma bonds and 4 pi-bonds
(b) 9 sigma bonds, 3 pi-bonds and 2-non-bonding electrons
(c) 8 sigma bonds and 5-pi-bonds
(d) 8 sigma bonds, 3 pi-bonds and 4 non-bonding electrons
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 7
10. The maximum number of aliphatic isomers for an alkene with molecular formula C4H8 is
(a) 2 (b) 3
(c) 4 (d) 5
11. Which of the following would be optically active ?
(a) tertiary - butanol (b) sec - butanol
(c) n-butanol (d) 4-chloro-1-hydroxybutane

12. For a compound containing two dissimilar asymmetric carbon atoms, the number of stereoisomers
is :
(a) 2 (b) 3
(c) 4 (d) 5

13. The number of isomers for the aromatic compounds having M. F. C7H8O is :
(a) two (b) three
(c) four (d) five

14. The number of possible isomers for the aromatic hydrocarbon having molecular formula C9H12 is:
(a) nine (b) six
(c) three (d) eight

15. The total number of monochloroisopentanes is :

(a) 4 (b) 5
(c) 3 (d) 2

16. The total number of isomeric optically active monochloroisopentanes is :

(a) two (b) three
(c) four (d) one

17. The spatial arrangement of atoms or groups in a stereoisomers is called :

(a) conformation (b) configuration
(c) inversion (d) none of these

18. Achiral stereoisomers which have chiral centers and possesses a symmetry of plane are called
(a) d (b) 
(c) d and  (d) meso

19. In which of the following organic compounds all the carbon atoms do not lie in one plane
(a) toluene (b) 2-butene
(c) neopentane (d) propene
20. Which of the following species is most stable ?
 
(a) p  NO C H  C H (b) C H C H
2 6 4 2 6 5 2
  
(c) p  Cl  C H  C H (d) H 3C O C 6 H 4  C H 2
6 4 2 

 E – Level

1. The total number of isomeric alcohols with the molecular formula C4H9OH is
(a) 5 (b) 4
(c) 3 (d) 2

2. The total number of isomeric trimethylbenzene is

\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 8
(a) 3 (b) 4
(c) 5 (d) 6

3. C6H5CHO + HCN — C6H5CH(OH)CN

The product would be
(a) optically active (b) a meso compound
(c) a racemate (d) a mixture of diastereomers

4. The number of geometrical isomers of

CH3CH = CH — CH = CH — CH = CHCl is
(a) 4 (b) 6
(c) 8 (d) 10

5. Tautomerism will be exhibited by

(a) R3CNO2 (b) RCH2NO2
(c) (CH3)2NH (d) (CH3)3CNO

6. A similarity between optical and geometrical isomerism is that

(a) if in a compound, one is present then so is the other
(b) each forms equal number of isomers for a given compound
(c) both are included in stereo isomerism
(d) they have no similarity

7. Which of the following pairs of compounds are enantiomers?

CH3 CH3 CH3 CH3
H OH HO H H OH HO H
(a) OH H and H OH (b) OH H and OH H
CH3 CH3 CH3 CH3

CH3 CH3
H OH CH3 OH H CH3
OH H H OH
H OH HO H
CH3 H OH CH3 HO H
(c) and (d) and
CH3 CH3
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 9
8. Which of the following Fischer’s projection formula is identical to D-glyceraldehyde?
CH2OH CH2OH

(a) HO C CHO (b) H C OH

H CHO
CHO CHO

(c) HO C CH2OH (d) H C CH2OH

H HO

9. The name of the following compound is

(a) (2Z, 4Z)-2, 4-hexadiene (b) (2Z, 4E)-2, 4-hexadiene

(b) (2E, 4Z)-2, 4-hexadiene (d) (2E, 4E)-2, 4-hexadiene

10. Which among the following carbocations is most stable:

C
(a) (b) C6H5—CH2

CH3—C—CH3
(c) C6H5—CH—C6H5 (d)
CH3
11. Consider the following compound:
CH2=CH–CH=CH2
1 2 3 4
carbon-carbon bond length between C2 and C3 will be:
(a) 1.54Å (b) 1.3 Å
(c) Less than 1.54Å and greater than 1.33Å (d) 1.21 Å
12. Consider the following three halides:
(1) CH3—CH2—Cl (2) CH2=CH—Cl (3) C6H5—Cl
Arrange C—Cl bond length of these compounds in decreasing order:
(a) 1 > 2 > 3 (b) 1 > 3 > 2
(c) 3 > 2 > 1 (d) 2 > 3 > 1
13. Consider the following compounds:
NH2 NH2 NH2 NH2

NO2 CN CH3
(1) (2) (3) (4)
Arrange these compounds in decreasing order of their basicity:
(a) 1 > 2 > 3 > 4 (b) 2 > 3 > 1 > 4
(c) 4 > 1 > 3 > 2 (d) 4 > 1 > 2 > 3
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 10
14. Consider the following compounds:
O
N N N N

H H H
(1) (2) (3) (4)
Order of basicity of these compounds in decreasing order is:
(a) 4 > 1 > 2 > 3 (b) 1 > 3 > 4 > 2
(c) 2 > 3 > 4 > 1 (d) 1 > 3 > 2 > 4

15. Which one of the following is most basic:

NH2 NH2
(a) (b) CH3

NH2
NH2
(c) CH3 (d)
CH3
CH3 CH3

16. Which one of the nitrogen containing compounds is an electrophile?

(a) NH2—NH2 (b) NH2—OH
(c) NF3 (d) NH3

17. Physical properties of a compound depend on:

(a) Primary forces present in the compound
(b) Secondary forces present in the compound
(c) Bond angle of the molecule
(d) Shape of the molecule

18. What is the correct increasing order of bond lengths of the bonds indicated as I, II, III and IV in
following compound:
IV
III
II

I
(a) I < II < III < IV (b) II < III < IV < I
(c) IV < II < III < I (d) IV < I < II < III
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 11
19. In which of the following structures the pair of starred carbon atoms do not lie in the same plane
* *
CH
H3C CH3 3
(a) C C (b)
CH3— H*2C H
*
* H H3 C *
CH2— CH3
CH C C C
(c) H (d)
H3 C H
* *

20. Which among the following statement is correct?

(1) CF2 is more stable than CCl2 (2) CCl2 is more stable than CBr2

(3) Singlet CH2 is more stable than triplet CH2

(4) Singlet carbene has planar geometry
(a) 1, 2 and 4 (b) 2 and 4
(c) 1, 2 and 3 (d) 2, 3 and 4
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 12

 MULTIPLE CORRECT ANSWERS TYPE

1. Which of the following compounds will show metamerism?
(a)CH3—O—C2H5 (b) CH3—O—CH3
(c) CH3—CO—C2H5 (d) C2H5—S—C2H5

2. The compound C4H10O can show:

(a) functional isomerism (b)metamerism
(c) position isomerism (d) tautomerism

3. An isomer of propanal is
(a) propane (b) methyl vinyl ether
(c) propenol (d) acetone
CH3
4. Consider the following organic compound, To make it a chiral compound,
CH3—CH—CH2—CH3.
1 2 3 4

the attack should be on carbon:

(a) 1 (b) 2
(c) 3 (d) 4

5. Which of the following will show geometrical isomerism?

(a) 1, 2-dibromobutene (b)isobutylene
(c) 2-butene (d) 1-chloropsopene

6. Which of the following has non zero dipole moment?

(a) 1-butene (b) cis-2-butene
(c) trans-2-butene (d) 2 methyl-1-propene

7. Which of the following does not show geometrical isomerism?

(a) 1, 1-dichloro-1-pentene (b) 1, 2-dichloro-1-pentene
(c) 1, 3-dichloro-1-pentene (d) 1, 4-dichloro-2-pentene

8. The following compound CH3CH = C(OH)—CH(OH)COOH can exhibit

(a) geometrical isomerism (b) optical isomerism
(c) Tautomerism (d) metamerism

9. Tautomerism is exhibited by
(a) CH = CH—OH (b) O O

O
O
O O
(c) (d)
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 13
10. Which of the following compounds donot exhibit stereo isomerism?
(a) 2-methylbutene-1 (b) 3-methylbutene-1
(c) 3-methylbutanoic-acid (d) 2-methylbutanoic-acid

11. Of the five isomeric hexanes, the isomer which can give more than one product on
monochlorination is/are
(a) n-hexane (b) 2, 3-dimethylbutane
(c) 2, 2-dimethylbutane (d) 2-methylpentane

12. Which of the following compounds will show geometrical isomerism?

(a) 2-butene (b) propene
(c) 1-phenyl propene (d) 2-emthyll but-2-ene
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 14

 REASONING TYPE
1. Statement-1: Melting point of alkyne is more than the corresponding alkane.
Statement-2: Alkyne has symmetrical (rod like structure) and hence, compact structure.

2. Statement-1: p-nitrophenol is ore acidic than o-nitrophenol.

Statement-2: Intramolecular hydrogen bonding decreases acidity of phenols.

3. Statement-1: Aliphatic secondary amine is more basic than tertiary amine in solution.
Statement-2: Degree of hydration of tertiary amine is very-very less.

4. Statement-1: Acetic acid and methyl formate are functional isomers. Acetic acid is sluble in water
whereas methyl formate is insoluble.
Statement-2: Intramolecular hydrogen bonding between solute and solvent decreases solubility of
solute in the solvent.

5. Statement-1: Melting point of fumaric acid is more than the maleic acid.
Statement-2: Melting point of symmetrical molecule is more than the unsymmetrical molecule.

6. Statement-1: 1,3 –cyclopentadiene is highly acidic in character.

Statement-2: Cyclopentadiene anion is aromatic.

7. Statement-1: 2, 4,6-cycloheptatriene cation is highly stable cation.

Statement-2: Planar, cyclic, conjugated compound having (4n+2)p-conjugated electrons is aromatic.

8. Statement-1: Chloroacetic acid is more acidic than bromoacetic acid.

Statement-2: —I group present is acid decreases acidity of the compound.

9. Statement-1: Pyridine is more basic than pyrrole.

Statement-2: Delocalisation decreases basicity of the compound.

10. Statement-1: Dipole moment of acetaldehyde is higher than that of formaldehyde.

Statement-2: Charge separation in acetaldehyde is more than the formaldehyde.

11. Statement-1: Carbon-carbon double bond length in 2-butene is more than 1-butene.
Statement-2:Hyperconjugations increases bond length of carbon-carbon double bond.

12. Statement-1: Propene is more acidic than propyne.

Statemetn-2: Acetylenic carbanion is more stable than vinylic carbanion.

13. Statement-1: Dipolemoment of vinyl chloride is less than the ethylchloride.

Statement-2: The chlorine atom invinyl chloride is less reactive due to +R effect.
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 15
14. Statement-1: n-Hexanol does not dissolve in water whereas ethanol dissolves.
Statement-2: +I group present on oxygen decreases strength of intermolecular hydrogen bonding.

15. Statement-1: Amides are less basic than primary amines.

Statement-2: Delocalisation of lone pair of electrons on nitrogen decreases basicity of the compound.

16. Statement-1: Methylisocyanide has a higher boiling point than methylcyanide.

Statement-2: Dipolemoment of methylisocyanide is more than the methylcyanide.

17. Statement-1: Stereoisomers which are not mirror images are called diastereomers.
Statement-2: Diastereomers may or may not be optically active.

18. Statement-1: CHBr=CHCl exhibits geometrical isomerism.

Statement-2: Presence of double bond is one of the condition of geometrical isomerism.

19. Statement-1: All the carbon atoms in 2-butene lie in one plane.
Statement-2: All the carbon atoms in 2-butene are sp2 hybridized.

20. Statement-1: Alkane having more than three carbon atoms exhibit chain isomerism.
Statement-2: All carbon atoms in alkane are in one plane.

21. Statement-1: The boiling point of alcohols is higher than those of hydrocarbons of comparable
molecular masses.
Statement-2: Alcohols show intramolecualr hydrogen bonding.

22. Statement-1: Tricyanomethane is as strong acid as a mineral acid.

Statement-2: The tricyanomethyl carbanion is highly stabilized by delocalisation and inductive
effect.

23. Statement-1: Tropylium cation is more stable than benzyl carbocation.

Statement-2: Tropylium cation maintains its aromatic character in all of its resonating structures
where as benzyl carbocation loses its aromatic character in some of the canonical forms.

24. Statement-1: Diastereomers are always optically active.

Statement-2: Diastereomers possesses different physical properties.

25. Statement-1: Although allenes do not have any asymmetric carbon, yet they are optically active.
Statement-2: Cause of optical activity is dissymmetry of the molecule.
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 16

 LINKED COMPREHENSION TYPE

Paragra
ph-1
Those compounds which rotate plane polarized light are optically active compounds. They must be
chiral. i.e. should not have any plane of symmetry. They may or maynot have chiral carbon atom(s).
Meso compounds are optically inactive due to internal compensation of optical rotation.
Questions:
1. Which of the following alkane shows optical isomerism?
(a) 2-methyl pentane (b) 3-methyl pentane
(c) 2, 3-dimethyl pentane (d) Both (b) and (c)

2. Which of the following are enantiomer?

(a) d-glucose and l-glucose (b) D-glucose and L-glucose
(c) Racemic-tartaric acid (d) Meso-tartaric acid

3. Which of the following is meso compound?

COOH COOH
H OH H OH
(a) (b)
HO H H OH
COOH COOH
CHO CHO
H OH
(c) (d) H OH
HO H
CHO CH2OH
Paragraph2
Isomers that are mirror images of each other are called enantiomers. Enantiomers have identical
physical properties except for the direction of rotation of the plane of polarized light.
The two 2methyl1butanols, for example have identical melting points, boiling points, densities,
refractive indexes.
(+)2methyl1butanol ()2methyl1butanol
Specific rotation +5.90° 5.90°
Boiling point 128.9°C 128.9°C
Relative density 0.8193 0.8193
Refractive index 1.4107 1.4107
Enantiomers have identical chemical properties expect toward optically active reagents. The two
lactic acids are not only acids, but acids of exactly the same strength that is dissolved in water at the
same concentration, both ionize to exactly the same degree.
A mixture of equal parts of enantiomers is called a racemic modification. A racemic modification is
optically inactive. They cannot be separated by ordinary methods; not by fractional distillation,
because their boiling points are identical, not by fractional crystallization, because their solubilities
in a given solvent are identical. The separation of a racemic modification into enantiomers is called
as resolution.
Stereoisomers that are not mirror images of each other are called diastereomers.
Diastereomers have similar chemical properties, since they are members of the same family.
Diastereomers have different physical properties, different melting points, boiling points, solubilities
in a given solvent, densities, refractive indexes and so on. Diasteromers differ in specific rotation.
As a result of their differences in boiling point and in solubility, they can in principal at least, be
separated from each other by fractional distillation or fractional crystallization.
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 17
Given a mixture of all four stereoisomeric 2,3dichloropentanes, we could separate it by distillation,
for example, into two fractions but no further. Further separation would require resolution of the
racemic modification by use of optically active reagents.
A meso compound is one whose molecules are super imposable on their mirror images even though
they contain chiral centers.
nbutane is allowed to undergo free radical chlorination and the reaction mixture is separated by
careful fractional distillation.
Questions:
1. How many fractions of formula C4H9Cl would you except to collect.
(a) two (b) three
(c) one (d) four
2. If we were to put the secbutyl chloride actually prepared by the chlorination of nbutane into a
polarimeter, would it rotate the plane of polarized light?
(a) no, because it is achiral
(b) yes, because it is chiral
(c) no, because prepared as described it would consist of the racemic modification
(d) no, because it is meso isomer
3. Monochlorination of (R)secbutylchloride at 300°C is carried out and the products are separated by
careful fractional distillation. How many fractions will be collected
(a) 4 (b) 5
(c) 3 (d) 2

4. Monochlorination of (R)secbutylchloride at 300°C is carried out and the products are separated by
careful fractional distillation. How many fractions are optically active?
(a) 2 (b) 3
(c) 4 (d) 1
Paragraph-3
Carvone shown in figure can exist as either of two enantiomers. CH3
O
One of them, (+)carvone, provides the characteristic odor in
caraway speed oil, whereas ()carvone is responsible for the
fragrance of spearmint oil. C
H3C CH2
Carvone
A chemist attempted to isolate (+)carvone from caraway seed CH3

oil, which consists almost entirely of (+)carvone and limonene

shown in figure.
C
H3C CH2
Limonene
Because the two compounds have very
different boiling points, the chemist decided
to separate them by vacuum fractional
distillation. The apparatus shown in figure
was assembled, and a sample of caraway
seed oil was placed in the distillation flask.
An ebulliator was lowered into the
distillation flask to introduce small air
bubbles into the system. The fractionating
column and distillation head were wrapped
with glass wool, and the apparatus was
connected with thick tubing to a vacuum
source. The contents of the distillation flask Fig. Vacuum fractional distillation
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 18
were heated and two fractions were apparatus
collected in the receiving flask.
Questions:
1. When the caraway seed oil is heated, which of the two components will most likely distill first?
(a) Limonene, because it has the lower boiling point
(b) Limonene, because it has the higher boiling point
(c) (+)Carvone, because it has the lower boiling point
(d) (+)Carvone, because it has the higher boiling point
2. The most likely function of the ebulliator is to
(a) keep the condensed vapors cool in the receiving flask.
(b) promote the establishment of a high vacuum in the system.
(c) prevent superheating of the liquid to be distilled.
(d) provide an outlet when the pressure inside the system becomes too high.
3. Which of the following experimental modifications will most likely improve the degree of separation
between limonene and (+)Carvone?
(a) Heating the distillation flask at a lower rate
(b) Using a vacuum source that can achieve a lower pressure inside the distillation apparatus
(c) Cooling the condenser with ice water
(d) Using a shorter fractionating column.

4. Carvone is shown below with certain carbon atoms labelled. CH3

2 O
(+)Carvone and ()Carvone differ in the orientation of the 3
1
substituents around which of the following carbon atoms? 4 5 6
(a) Carbon 2 only (b) Carbon 5 only
(c) Carbons 2 and 5 only (d) Carbons 2, 5 and 7 only C
7
H3C CH2

5. If a leak develops in the vacuum distillation apparatus, the boiling points of the two components of
caraway seed oil will
(a) both increase (b) both decrease
(c) both remain the same (d) become more similar
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 19

 MATRIX MATCH TYPE

1.
ColumnI ColumnII
(A) trans-1, 4-dimethyl cyclohexane, and cis-1, 4- (p) Can be isolated in pure forms
dimethyl cyclohexane (both chair forms)
(B) trans-1, 4-dimethyl cyclohexane, (diaxial) and (q) Geometrical isomers
(diequitorial) both chair form
(C) cis and trans But-2-ene (r) Conformers
(D) (+)–Lactic acid and ()–Lactic acid (s) Differ in melting point
2.
Column-I Column-II
(A) Inductive effect (p) Delocalisation of sigma electron with p bond
(B) Resonance effect (q) Strong effect
(C) No bond resonance (r) Permanent effect
(D) Electromeric effect (s) Delocalisation of p electrons
3.
Column I Column II
(A) Singlet carbene (p) Paramagnetic
(B) Triplet carbene (q) Diamagnetic
(C) Carbocation (r) sp2 hyrbrid carbon
(D) Free radicals (s) Angular geometry
4.
ColumnI ColumnII
(A) Cyclopropenyl carbocation (p) Hyperconjugation
(B) Cyclopentadienyl anion (q) All carbon atoms are sp2 hybridized
(C) Benzyne (r) Aromatic in nature
(D) tropylium ion (s) Planar geometry
5.
Column– I (Organic compound) Column– II (pKa value)
(A) CH3COCH2COOC2H5 (p) 17
(B) CH3COCH2COCH3 (q) 8.9
(C) OHC  CH2  CHO (r) 5
(D) CH3CHO (s) 5
6.
Column – I Column – II
(A) (p) 4n p electrons

(B) (q) (4n + 2)p electrons

(C) (r) Aromatic

(D) (s) Non-aromatic

O

ANSWERS
 STRAIGHT OBJECTIVE TYPE
 O – Level
1. a 2. d 3. c 4. c 5. b
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 20
6. a 7. a 8. b 9. d 10. c
11. a 12. d 13. b 14. b 15. b
16. d 17. c 18. b 19. c 20. d
21. a 22. b 23. a 24. d 25. d

 I – Level
1. d 2. a 3. c 4. c 5. c
6. b 7. c 8. c 9. b 10. c
11. b 12. c 13. d 14. d 15. a
16. a 17. a 18. d 19. c 20. d

 E – Level
1. b 2. a 3. c 4. c 5. b
6. c 7. a 8. c 9. d 10. a
11. c 12. a 13. c 14. d 15. c
16. c 17. b 18. d 19. d 20. a

 MULTIPLE CORRECT ANSWERS TYPE

1. d 2. a, b, c 3. b, c, d 4. a, c 5. a, c, d
6. a, b, d 7. b, c, d 8. a, b, c 9. a, c, d 10. a, b, c
11. a, b, c, d 12. a, c

 REASONING TYPE
1. a 2. a 3. a 4. c 5. a
6. a 7. a 8. c 9. a 10. a
11. a 12. d 13. b 14. a 15. a
16. a 17. a 18. b 19. a 20. c
21. c 22. a 23. a 24. d 25. a

 LINKED COMPREHENSION TYPE

Paragraph-1
1. c 2. a 3. b

Paragraph-2
1. a 2. c 3. b 4. b

Paragraph-3
1. a 2. d 3. a 4. b 5. a
\ FUNDAMENTALS – GENERAL ORGANIC CHEMISTRY CH 21

 MATRIX MATCH TYPE

1.
A-p, q, s B-r, C-p, q, s, D-p
2. A-r, B-q, r, s, C-r, p, D-s
3. A-q B-q, r, s, C-q, r, D-p, r
4. A-q, r, s, B-r, s, C-r, s, q, D-q, r, s
5. A-r, B-q, C-s, D-p
6. A-q, s, B-p, s, C-q, s, D-q, r