GENERAL ORGANIC CHEMISTRY JEE ADVANCED - VOL - IV

PREVIOUS YEARS IIT - JEE QUESTIONS

1. Amongst the following, the most basic compound is [IIT-90]
(A)benzylamine (B)aniline (C)acetanilide (D)p-nitroaniline
2. The formation of cyanohydrin from a ketone is an example of [IIT-90]
(A)electrophilic addition (B) nucleophilic addition
(C)nucleophilic substitution (D) electrophilic substitution
3. The enolic form of acetone contains [IIT-90]
(A)9 sigma bonds, 1 pi bond and 2 lone pairs (B)8 sigma bonds, 2 pi bond and 2 lone pairs
(C)10 sigma bonds, 1 pi bond and 1 lone pairs (D)9 sigma bonds, 2 pi bond and 1 lone pairs
4. The hybridisation of carbon atoms in C–C single bond of is [IIT-91]
(A)sp3 – sp3 (B)sp2 – sp3 (C)sp – sp2 (D)sp3 – sp
5. Isomers which can be interconverted through rotation around a single bond are [IIT-92]
(A)conformers (B)diastereomers (C)enatiomers (D)positional isomers
6. How many optically active steroisomers are possible for butane-2, 3-diol? [IIT-97]
(A)1 (B)2 (C)3 (D)4
7. The optically active tartaric acid is named as D-(+)-tartaric acid because it has a positive [IIT-99]
(A)optical rotation and is derived from D-glucose
(B) pH in organic solvent
(C)optical rotation and is derived from D-(+)-glyceradehyde
(D)optical rotation when substituted by deuterium
8. Which of the following compounds will exhibit geometrical isomerism? [IIT-2000]
(A)1-pheyl-2-butene (B)3-phenyl-1-butene (C)2-phenyl-1-butene (D) 1, 1-diphyenyl-1-propene
9. The number of isomers for the compound with molecular formula C2BrClFI is [IIT-01]
(A)3 (B)4 (C)5 (D)6
10. Which of the following compounds exhibits, stereoisomerism? [IIT-02]
(A)2-methyl butene-1 (B) 3-methyl butyne-1
(C)3-methyl butanoic acid (D) 2-methyl butanoic acid
11. Which of the following compounds hydrocarbons has the lowest dipole moment? [IIT-02]

(A) (B)CH3–HC=HC–CH3 (trans)

H H
(C)CH3–CH2CH=CH2 (D) CH2=CH–CH=CH2
12. Which of the following represent the given mode of hybridisation sp2–sp2–sp–sp from left to
right? [IIT-03]
(A) (B) C) (D)
13. Among the following, the molecule with the highest dipole moment is [IIT-03]
(A) CH3Cl (B) CH2Cl2 (C) CHCl3 (D) CCl4

14. C2 is rotated 120° about C2–C3 bond. The resulting conformer is [IIT-04]

(A)partially eclipsed (B)eclipsed (C)gauche (D)staggered

15. Arrange in order of increasing acidic strength [IIT-04]

(A)X > Z > Y (B)Z < X > Y (C)X > Y > Z (D) Z > X > Y
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16. Which of the following resonating structures of 1-methoxy-1, 3-butadiene is least stable?
[IIT-05]
(A) (B)

(C) (D)
17. 4-methyl benzene sulphonic acid reacts with sodium acetate to give [IIT-05]

(A) SO3Na , CH3COOH (B) COONa, SO

3

(C) OCOCH3 , SO3 (D) SO3H, NaOH

18. The IUPAC name of C6H5COCl is [IIT-06]

(A)benzoyl chloride (B)benzene chloro ketone
(C)benzene carbonyl chloride (D)chloro phenyl ketone
19. The number of stereoisomers obtained by bromination of trans-2-butene is [IIT-07]
(A)1 (B)2 (C)3 (D)4
20. Among the following, the least stable resonance structure is [IIT-07]

(A) (B) (C) (D)

21. Hyperconjugation involves overlap of the following orbitals [IIT-08]

(A) (B) (C) (D)
22. The correct stability order for the following species is [IIT-08]

(A) (II) > (IV)> (I) > (III) (B) (I) > (II)> (III) > (IV)
(C) (II) > (I)> (IV) > (III) (D) (I) > (III)> (II) > (IV)

23. Among the following compounds, the most acidic is [IIT-11]

(A) p - nitrophenol (B) p -hydroxybenzoic acid
(C) O - hydroxybenzoic acid (D) p - toluic acid
24. In allene, CH 2 C CH 2 the type (s) of hybridization of the carbon atoms is (are)
(A) sP and sP 3 (B) sP and sP 2 (C) only sP 2 (D) sP 2only sP 3
25. The number of optically active products obtained from the complete ozonolysis of the given
compound is [IIT-12]
CH3 H

-CH=CH -CH3
H3C -CH= CH - C -CH= CH -C

H CH3
(A) 0 (B) 1 (C) 2 (D) 3
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26. The molecule(s) that will have dipole moment is/are
(A)2, 2 dimethyl propane (B) trans 2-pentene
(C) cis 3-hexene (D) 2, 2, 3, 3-tetramethyl butane
27. What is the decreasing order of strength of the bases?

(A) (B)
(C) (D)
28. The correct statement(s) about the compound given below is (are)

(A)the compound is optically active (B) the compound possesses centre of symmetry
(C) the compound possesses plane of symmetry (D) the compound possesses axis of symmetry
29. The bond energy (in kcal mol-1 ) of a C-C single bond is approximately
(A) 1 (B) 10 (C) 100 (D) 1000.
30. In the Newmann projection for 2,2-dimethylbutane [IIT-10]

X and Y can resective be

(A) H and H (B) H and C2H5 (C) C2H5 and H (D) CH3 and CH3
31. Which of the given statements (s) about N,O,P and Q with respect to M is (are) correct?
[IIT-12]
OH Cl
OH H H
O) H

)
M OH
Cl
N)H CH3 OH
OH
H OH H

CH 3 Cl CH 3

P) CH 3 CH 3
Q)
H OH HO H

HO H HO H

Cl Cl
(A) M and N are non- mirror image stereoisomers (B) M and O are identical
(C) M and P are enantiomers (D) M and Q are identical
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32. Among the given options, the compounds(s) in which all the atoms are in one plane in all the
possible conformations (if any, is (are) [IIT-11]
H H H
C C H C C C
(A) (B)
H 2C CH 2 CH 2
(C) H 2 C C O (D) H 2 C C CH 2

INTEGER QUESTIONS

33. The total number of cyclic isomers possible for a hydrocarbon with the molecular formula is
C4H6. [IIT-10]
34. The maximum number of isomers (including stereoisomers) that are possible on mono chlorination
of the following compound, is [IIT-11]
CH 3

CH 3 CH 2
H CH 2 CH 3
35. The total number of contributing structures showing hyperconjugation (involving C - H bonds)
for the following carbocation is [IIT-11]
H 3C + CH 2 CH 3

PREVIOUS IIT - JEE 2013 QUESTIONS :

36. The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are due to
(A)   p (empty) and   * electron delocalisations
(B)   * and    electron delocalisations
(C)   p (filled) and    electron delocalisations
(D) p (filled)  * and   * electron delocalisations

ADDITIONAL QUESTIONS

BASIC ORGANIC CHEMISTRY

1. Which of the following is favourable for the compound to be purified by sublimation?

(A) high vapour pressure of the compound below its melting point
(B) low vapour pressure of the compound
(C) get decomposed on heating
(D) moderate vapour pressure of the compound
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GENERAL ORGANIC CHEMISTRY JEE ADVANCED - VOL - IV
2. Two volatile and miscible liquids can be separated by fractional distillation into pure components
under the condition when
(A) they have low boiling point (B) the difference in their boiling points is more
(C) the difference in their boiling points is less (D) they have high boiling points.
3. 0.365 g of an organic compound containing nitrogen gave 56mL of nitrogen at STP. The percentage
of nitrogen in the compound is
(A) 19.18 (B) 38.36 (C) 9.18 (D) 29.18
4. 0.12g of an organic compound gave 0.22g by the usual analysis. The percentage of phosphorous
in the compound is
(A) 15.23 (B) 38.75 (C) 51.20 (D) 60.92
5. Carbon and hydrogen are estimated by heating organic compound in excess of air and
(A) copper (III) oxide (B) copper (II) oxide (C) CuSO4 (D) CuCl2
6. Assertion (A): In the fractional distillation when the vapours of liquid mixture passed through
fractionating column the liquid with high B.Pt. condenses and those with low B.Pts pass over
through condensor.
Reason (R): compounds with more difference of BP’s undergo fractional disitllation.
7. Assertion (A): In Duma’s method when an organic compound is heated with cupric oxide, ‘N’ is
converted to N2 gas.
Reason (R): Cupric oxide oxidized carbon and hydrogen to CO2 and water vapour.
8. Assertion (A): In Kjeldahl’s method, nitrogen in organic compound is converted to NH3 gas.
CuSO4 (NH4)2SO4
Reason (R): Organic compound + H2SO 4

(NH4)2SO4+ 2NaOH Na2SO4 + 2H2O + 2NH3

9. The IUPAC name of is:

(A) Bicyclo [3.2.1] octane (B) Bicyclo [3.2.2] octane

(C) Spiro [3.2.1] octane (D) Bicyclo [5.2.1] octane

10. The IUPAC name of is:

(A) Bicyclo [2.2.2] octane (B) Bicyclo [2.2.1] octane

(C) Bicyclo [2.2.0] octane (D) Bicyclo [1.1.1] octane
11. The struture for Bicyclo [2.2.1] heptane is :

(A) (B) (C) (D) None of these

12. The name of the compound is

(A) (2Z,4Z) – 2,4 – Hexadiene (B) (2Z,4E) – 2,4 –Hexadiene
(C) (2E,4Z) – 2,4 –Hexadiene 4) (2E,4E) – 2,4 –Hexadiene
13. The reducing agent used in the reduction of alkyl halide to get alkane is
(A) (B) (C) (D)

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KEY
PREVIOUS YEARS IIT QUESTIONS

1. (A) 2.(B) 3.(A) 4.(A) 5(A) 6(B) 7.(C) 8(A)

9(D) 10.(D) 11.(B) 12.(A) 13.(A) 14.(C) 15.(A) 16.(C)
17.(A) 18.(A) 19.(A) 20.(A) 21.(B) 22.(D) 23.(B, C) 24.(A)
25.(A, D) 26. C 27. C, D 28.A,D

ADDITIONAL QUESTIONS

1. (A) 2. (C) 3. (A) 4. (C) 5.(B) 6.(C) 7.(B) 8.(A)

9.(A) 10.(A) 11.(A) 12.(D) 13.(A)

HINTS
PREVIOUS YEARS IIT HINTS

11. For CH3 – CH = CH–CH3, m = 0, because this molecule is symmetrical planar.

H H
 
   
 H–C =
 C –– C 
 CH
12. In H 2C = CH – C  N
 2 2
sp sp sp sp
13. The dipole moment of a polar molecule depends upon its geometry. A symmetrical molecule is non-polar
even though it contain polar bonds. Methane molecule (CH4) has zero value of dipole moment due to its
symmetric structure. We know that the bond dipole moment of C – H bond of C – Cl bond reinforce
one another.
In CHCl3, the resultant of C–H and C – Cl dipoles oppose the resultant of two C – Cl dipoles while in
oppose the resulant of two C–H dipoles adds to resultant of two C–Cl. In case of CH3Cl, the resultant of
two C–H two C–Cl. In case CH3Cl, the resultant of two C–H dipole adds to the resultant of two C–Cl.
In case CH3Cl, the resultant of two C–H dipoles add to the resultant of C–H and C–Cl dipoles. Thus,
dipole moment of CH3Cl is highest among the given compounds. The molecule (CCl4) again becomes
symmetrical and dipole moment reduces to zero.
CH3
H H
3
14. 2 Here, when C2 is rotated clockwise 120° about C2–C3 bond, the resulting conformer is
H H
CH3
Gauche conformer.
CH3 H
H H H H
3 On 120° 2
Hence, 2 rotation in clockwise 3
H H direction H CH3
CH3 CH3

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GENERAL ORGANIC CHEMISTRY JEE ADVANCED - VOL - IV
15. pKa value of carboxylic group is less than pKa of in amino acid and (Z) will have comparatively less pKa

than NH –(Y) due to –I effect of carboxylic group. We know that acidic strength is inversely proportional
3
to pKa.
Hence, correct order of acidic strength is
 
CO2H   NH3   NH3
(X) (Z) (Y)
16. The octet of all atoms are complete is structures a and b. The molecule in which all the atoms have
complete octer is more stable than atom which have incomplete octer. Larger the number of resonating
structures, larger will be the stability, thus structures a and b are stable.
In structure (d), the electron deficiency of positive charged carbon is duly compensated by one pair
electrons of adjacent oxygen atoms while such neighbour group support is not available in structure (c).
Hence, structure (c) is least stable in comparision to structure (d).
17. 4-methyl benzene sulphonic acid is stronger acidic than acetic acid thus it wil release acetic acid from
sodium acetate.
COCl

18.
benzoyl chloride

19.

20. Two positive charges present at the adjacent places, elevates the energy, thus lowers the stability most.

21. Hyperconjugation is one kind of delocalisation of s(C–H) bonded electron to unshared p-orbital
H H H
  
–C––CH––CH2 –C––CH2+ –C––CH2

2 2 2
sp sp sp
26. I > III > II > IV

+M effect, hyperconjugation (6Hs) and + I effect (2–Me groups)
O

+M effect, hyperconjugation (3Hs) and +I effect (1 – Me group)
O

Hyperconjugation (5Hs) and +I effect
(2°carbocation)


Hyperconjugation (2Hs) and +I effect
(1°carbocation)
29. C-C single bond dissociation energy ranges between 88 to 150 K cal mol-1
CH3

H3 C  C  CH2  CH3
30. 1 2 3 4
CH3

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2,2- dimethyl butane
H
CH 3 CH 3 CH 3 CH 3
H H
0
180

rotation

C1 - C 2 rotation
H H

H C2H5 C2 H5

H
CH3 CH3 H3C CH3
CH3 H H
0
180
H3C  C  CH2  CH3 
rotation

X and Y become H and H H
CH3 CH3
CH3 CH3

33. Cyclic isomers of C4H6 are

H2C
CH3
Total Isomers = 5
36. t-butyl carbocation is stabilized by   p overlapping.
2-butene is stabilized by   * overlapping.

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