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General Organic Chemistry - Part 1
1. Hybridisation in Organic Chemistry Q 1. The concept of hybridization is given
(A) to know the structure of a chemical species
(B) to explain the structure of a chemical species
given by VSEPR model
(C) to know the more stable structure
(D) to do energy conservation
Q 2. The process of hybridization is
(A) Exothermic (B) Endothermic
(C) Neither Exothermic nor Endothermic
(D) can be Exothermic or Endothermic
Q 3. Direct participation of atomic orbital of carbon in
CH4 molecule formation leads to
(A) Bond angle equal to 90o
(B) Bond angle equal to 109o28’
(C) Three C – H bonds are equivalent
(D) both A & C
Q 4. Which of the following is NOT characteristics of
hybridization?
(A) it is intra-atomic porcess
(B) No of orbitals remained conserved in
hybrisiation.
(C) Hybridisation can happen between any set of
atomic orbitals.
(D) In any molecule, hybridistion may or may not
occur
Q 5. When ground state C-atoms are subjected to
react, they normally undergo three process –
excitation, hybridization and bonding
simultaneously . Now which of the following
statements is (are) true
(A) Excitation is endothermic , hybridization is
exothermic and bonding is endothermic
(B) All are exothermic
(C) All are endothermic
(D) Excitation is endothermic hybridization is
neither exothermic nor endothermic and bonding
is exothermic.
Q 6. Which of the energy relations is(are) correct?
(A) E2p > E2sp3 > E2sp2 > E2sp > E2s
(B) E2s > E2sp > E2sp2 > E2sp3 > E2p
(C) E2sp2 = E2s > E2p +E2p+E2p
(D) E2sp3 = E2s + E2p + E2p + E2p
Q 7. Which of the following is the correct order of size
(A) 2s > 2sp > 2sp2 > 2sp3 > 2p
(B) 2p > 2sp3 >2sp2> 2sp > 2s
(C) 2sp3 > 3p > 2p
(D) 2sp3 > 3s > 2s
Q Q 8. In 2sp hybridization, 2s orbital can be mixed with
(A) Only 2px (B) Only 2py
(C) Only 2pz
(D) any one of 2px- 2py and 2pz
Q 9. In sp2 orbital, character of pz will be
(A) always 33.33% (B) always 0%
(C) always 66.66% (D) either 33.33% or 0%
Q 10. In sp3orbital
(A) Characters of px, py and pz are equal
(B) Character of s, px,py and pz are equal
(C) s-character is more than pz character
(D) Character of px,py and pz are not equal
Q 11. Which is the correct order of electronegativity?
[CBSE PMT 2006]
(A) sp3C > sp2C > sp3C
(B) spC > sp2C > sp3C
(C) sp2C > sp C > sp3C
(D) sp3C > sp C > sp2C
Q 12. The relative strength of the σ-bond formed
between SP3 – SP3, SP2 – SP2, and SP – SP
(A) 2: 1.99 : 1.93 (B) 2: 1.93 : 1.73
(C) 1.99 : 1.93: 1.73 (D) None of these
Q 13. Overlapping powers (overlap integrals) of 2s, 2p,
2sp3, 2sp2 and 2sp orbitals are in the order
(A) 2s>2p>2sp3>2sp2>2sp
(B) 2p>2s>2sp3>2sp2>2sp
(C) 2sp3>2sp2>2sp>2p>2s
(D) 2sp3>2sp2>2sp>2s>2p Q 14. Which of the following statements is/are true
about for C – O bonds of
(A) Two C-O bonds are formed by sp2 –sp3
overlaps and two C-O bond are formed by sp-sp
overlaps.
(B) Two are formed by sp –p overlaps and two
are formed by sp –p overlaps.
(C) All four C-O bonds are formed by sp-sp
overlaps.
(D) All four C-O bonds are formed by sp-p
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overlaps. Both C-N bonds are formed by sp2 –sp3
overlaps.
Q 15. In this molecule.
NHC
H
(A) both C-N bonds are formed by sp2- sp2
overlaps.
(B) one C-N bond is formed by sp2-sp2 overlaps
while the other by sp2 –sp3
(C) both C-N bonds are formed by sp2-sp3
overlaps.
(D) one C-N bond is formed by sp2-sp3 overlaps
while the other by sp3-sp3 overlap.
Q 16. Assertion (A): All the carbon atom in
CH2=C=CH2 are SP2 hybridised.
Reason (R): In this molecule, all carbon atoms
are attached together by double bonds.
. [NCERT Examaplar]
(A) Both A & R are correct and R is the correct
explanation of A
(B) Both A & R is correct but R is not correct
explanation of A
(C) Both A & R are not correct
(D) A is not correct but R is correct
Q 17. CH2=C=CH2, In this molecule
(A) All C-atoms are sp2-hybridized.
(B) Two C-atoms are sp2- hybridized and one C-
atom is sp-hybridized.
(C) All carbons are sp hybridized
(D) None of the C-atoms is hybridized.
Q 18. Which of the following compounds has
maximum number of sp-hybridized C-atoms?
(A) (CN)2
(B) H2C=CH-CN
(C) HC C–CH2 –CH= C=C=CH2
(D) CH2= C=CH–CN
Q 19. The compound 1,2-butadiene has [IIT JEE 1983]
(A) only sp hybridised carbon atoms
(B) only sp2 hybridised carbon atoms
(C) both sp and sp2 hybridised carbon atoms
(D) sp, sp2 and sp3hybridised carbon atoms
Q 20. Which of the following possess a SP carbon in its
structure? [CBSE PMT 1989]
(A) 3CH CHCl COOH− −
(B) H C C Cl− −
(C) Cl CH CH Cl− = −
(D) 2 2ClCH CH Cl−
2. Characteristics of Hybridisation
Q 1. Molecule in which the distance between the two
adjacent carbon atoms is largest is
(A) ethane (B) ethane
(C) ethyne (D) benzene
Q 2. The bond between carbon atom (1) and carbon
Atom (2) in compound 2N C CH CH − =
Involves the hybrids as [1987-IIT]
(A) sp2 and sp2 (B) sp3 and sp
(C) sp and sp2 (D) sp and sp
Q 3. The hybridisation of carbon atoms in C-C single
bond HC C-CH=CH2 is [1991-IIT]
(A) sp3-sp3 (B) sp2-sp3
(C) sp-sp2 (D) sp3-sp
Q 4. In the compound CH2=CH-CH2-CH2-C CH the
C2-C3 bond is of the type [1999 IIT]
(A) sp-sp2 (B) sp3-sp3
(C) sp-sp3 (D) sp2-sp3
Q 5. The number of sigma and pi-bonds 1-butene-3-
yne are [1989-IIT]
(A) 5 sigma and 5 pi (B) 7 sigma and 3 pi
(C) 8 sigma and 2 pi (D) 5 sigma and 4 pi
Q 6. How many σ and bonds are there in the
molecules of tetracyanoethylene ?
(A) Four σ and fourteen bonds
(B) Five σ and thirteen bonds
(C) Eight σ and ten bonds
(D) Nine σ and nine bonds
Q 7. Allyl Isocynide has [IIT 1995S]
(A) Nine σ and four bonds
(B) Eight σ and Five bonds
(C) Nine σ, Three bonds & 2 non bonded e–
(D) Eight σ, three bonds & 4 non bonded e–
Q 8. The C-H bond distance is the longest in
[1989-IIT]
(A) C2H2 (B) C2H4
(C) C2H6 (D) C2H2Br2
Q Q 9. The carbon-chlorine bond is the shortest in
(A) CH3-Cl (B) C6H5-CH2-Cl
(C) CH2 = CH-Cl (D) CH2=CH-CH2-Cl
Q 10. The x yC C− bond length order in
CH – CH – CH = CH3 2 2
X Y
(i)
CH – CH = C = CH3 2
X Y
(ii)
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(A) i ii iii (B) iii ii i
(C) ii iii i (D) iii i ii
Q 11. The bond length order of indicated bonds in
following molecules are
(1) (2)
(3) (4)
(A) 4 1 2 3 (B) 4 1 3 2
(C) 4 3 1 2 (D) None of these
Q 12. The total number of bond angles in
3 2CH CH CH− = is
(A) 10 (B) 12
(C) 8 (D) 16
Q 13. The Cl – C – Cl angle in 1,1,2,2 –
tetracholoroethene and tetrachloromethane
respectively will be about [IIT – 1988]
(A) 120o & 109.5o (B) 90o& 109.5o
(C) 109.5o & 90o (D) 109.5o & 120o
Q 14. The total number of bond angles in
is
(A) 8 (B) 7
(C) 12 (D) None of these
Q 15. Which of the following is a planar molecule?
(A) 3 2CH CH CH− = (B) 2CH C OH= −
(C) 2H C NH= (D) None
Q 16. Which of the following is a planar molecule?
(A) 2 2CH C CH= =
(B) 2 2CH C C CH= = =
(C) (D)
Q 17. In which of the following molecules, all atoms are
coplanar? [NEET 2016 - II]
(A) (B)
(C) 3 2 2( ) ( )CH C C CN= (D)
Q 18. Indicate the hybridization of all atoms (except H
atoms) in following molecules.
(A) (B)
(C) (D)
(E) (F)
(G)
(H)
(I) (J)
(K) (L)
(M) (N)
(O) (P)
Q 19. In which of the following molecules all atoms are
In one plane (Molecule is Co-planar)?
CH – CH – CH – CH3 2 2 3
X Y
(iii)
H – C C – H H – C N
H C = O2 H C = CH2 2
CH – C – NH3 2
O
ICl
F Br
CH3
CH – C – CH = CH3 2
O
CH CONH3 2
CH CH COOCH3 2 3
CH = C = O2
CHO
CHOCOOH
COOH
CH = C = CH – C C – CH2
CN
CHOCH NO3 CH – O – N = O3
O
CH – C – CH3 3
O
CH CN3 CH – OH3
CH – OH3 2
3
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(A) (B)
(C) ( )4
C CN (D)
(E) (F)
(G) (H)
(I) (J)
(K) (L)
Q 20. In which of the following molecule all bonds
angles are similar?
(A) (B)
(C) (D)
(E) (F)
(G)
(H)
(I)
(J) (K)
Q 21. How many bond angles are present in following
Molecules?
(A) (B)
(C)
(D) CH2O (E) CH3COCH3
(F) CH2=CH-CH=CH2
3. Resonance
Q 1. In 23CO −
, which statement is true ?
(A) one C-O bond has double bond character &
two C-O bond has single bond character
(B) one C-O bond length is smaller than other
two C-O bond length
(C) All three C-O bonds are identical
(D) 3 C-O bonds are different from each other
Q 2. Delocalization of electrons increases molecular
stability because
(A) electrons-nuclei attraction increases
(B) electron- electron repulsion decreases
(C) Potential energy of the molecule increases
(D) Potential energy of the molecule decreases
Q 3. Which of the following statements is Not true
about resonance?
(A) Resonance is an intramolecular process.
(B) Resonance involves delocalization of both
Electrons & Atoms.
(C) Resonance involves delocalization of
electrons only.
(D) Resonance decreases potential energy of a
molecule.
CH2
C
CH2
C = C
CN
CN
NC
NC
Br
OO
O
O
O
COOCH3
COOCH3
CHO
CH3
CH = CH – CH = CH – OCH2 3
CH = C = CH2 2
CH = CH – CHO2
CH2
O
CHO
CHO
– CH – CH2 3
O
O
H2C = CH – CN
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Q 4. Which of the following statements is (are) true
about resonance?
(A) Resonance has no effect on the potential
energy of a molecule.
(B) Any resonating molecule is always more
stable than any non-resonating molecule.
(C) The canonical structure explains all features
of a molecule.
(D) The resonance hybrid explains all features of
a molecule.
Q 5. All canonical structures of molecule
(A) must have different numbers of paired
electrons.
(B) need not be always equivalent but they should
not differ much in stability.
(C) should be always equivalent
(D) must have electrons in different orbitals.
Q 6. Resonance energy is
(A) equal to the energy of resonance hybrid.
(B) equal to the energy of most stable canonical
structure.
(C) equal to the difference in energy of the least
stable canonical stable to romance hybrid.
(D) equal to the difference in energies of the most
stable canonical structure & resonance hybrid.
Q 7. In which of the given lone pair of electrons are
not in same plane with the P P− bonds
(A) (B)
(C) 2 2CH CH N CH• •
= − = (D)
Q 8. In which of the following, resonance is not
possible
(A) (B)
(C) (D)
Q 9. Which of the following groups can not participate
in resonance with other suitable group?
(A) (B)
(C) (D)
(E) (F)
(G) (H)
(I) (J)
(K)
Q 10. Which of the following groups can either donate
or withdraw a pair of electrons in resonance
depending upon situation?
(A) 2NO− (B) NO−
(C) 2CH CH− = (D) CHO−
(E) 2NH− (F) N NH− =
(G) Ph−
(H) (I)
(J) Q 11. Write the canonical structures and resonance
hybrid of each of the following?
(A) 3 2CH NO (B) 3CH COOH
(C) 3CH COONa (D)
(E) 2H N CHO−
(F) 2 2CH CH CH
= −
(G) (H)
(I) 2 2CH CH CH
= − (J) 2 2CH CH CH•
= −
(K) 2R CO CH CH− − =
– COOH – COO
– COCl – NH3
– CH2
– CH2
CH = N –2
CH3
O N2 MeO
CH3
CH = CH – N2
CH 3
CH 3
N
H
O O
(L) BH
2 (M) PPh3
CH = CH-
CH- 2
-CH – CH 2 2
CH = O - 2
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(L) 2 3CH O CH CH NMe
− = −
(M) RCOCl (N) 2HCONH
(O) (P)
(Q) 2CH CH CH O= − = (R)
2CH C CH
= =
(S) 2CH CH C CH− − =
(T) 2 2CH CH CH CH= − =
(U) (V)
(W) 2CH N N
= = (X) 2CH C O= =
(Y) (Z)
Q 12. In which of the following charges is not
resonance stabilized, show by writing canonical
structures?
(A) (B)
(C) 2CH CH
= (D) 2CH CH CH O
− = −
(E) 3 2CH O CH
= − (F) 2 2CH O CH CH
= − =
(G)
(H)
(I) 2 3CH CH N Me
= −
(J) 2 2 2CH CH CH CH
= − −
(K) 2 3CH CH P Me
= −
(L) (M)
(N) (O) 2CH C CH
= =
(P) 2CH C CH
= =
Q 13. The bond order of Carbon Carbon bonds in
benzene is [IIT – 1981]
(A) one (B) Two
(C) between one & two
(D) one & two, alternatively
4. Drawing Resonating Structure
Q 1. Which of the following is correct order of +R
effect of groups
I. II.
III. IV.
(A) II I III IV (B) I II III IV
(C) II III I IV (D) IV III II I
Q 2. Which of the following is correct order of –R
effect of groups
I. 2NO− II. CN−
III. IV.
(A) I II III IV (B) I III II IV
(C) IV III II I (D) I IV III II
Q 3. In which of the given example 2CH CH= −
does not act as +R group?
OH
O
O
O
N
CH2
N|
H
N|
H
CH2 = C – CH = CH3
CH2 = O – CH = CH2
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(A) (B)
(C) (D)
Q 4. In which of the given example, 2CH CH= −
does not act as R− group
(A) (B)
(C) (D)
Q 5. How many lone pair of electrons participated in
resonance in the given compound
(A) 5 (B) 1
(C) 4 (D) 2
Q 6. In which of the given lone pair of nitrogen is not
participated in resonance
(A) (B)
(C) (D) None of these
Q 7. In which of the given resonance between two
benzenoid ring is not possible
(A)
(B)
(C)
(D) None of these
Q 8. The incorrectly matched total number of
resonance structure (RS) is
(A)
(B)
(C)
(D)
Q 9. In which of the given compound resonance is
possible ?
(A) 2 3CH CH SiH= − (B) 2 2CH CH BH= −
(C) 2 2CH CH NH= − (D) All of these
Q 10. In the given compound ?
(A) 2NO− acts as R− group
(B) 2NH− act as R+ group
(C) OH− does not act as +R group
(D) All of these
Q 11. Which of the following is not a permissible
resonating form
(A) (B)
(C) (D)
Q 12. Which of the following pairs is not a resonating
structures?
(A)
N
N
H
N
:
:
: :
N
:
= CH2
N
NH2:
CH3 CH3
N
:
CH3CH3
CH3CH3
N
:
CH3CH3
CH3CH3
O N2
CH3
CH3
CH3
NO2
Br
BrCH3
CH3 NO2
:
R.S = 5
SO R.S. = 64
2–
CH = CH – CH = CH – CH R.S. = 32 2
:
PO R.S. = 34
3–
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(B)
(C)
(D)
Q 13. Which of the following is not resonating structure
of diazomethane?
(A) (B)
(C) (D) All of these
Q 14. Which of the following pairs of structure do not
represent resonating structures?
(A)
(B)
(C)
(D)
5. Stability of Resonating Structures
Q 1. A canonical structure will be more stable if
(A) it has more number of bonds than if it has less
number of bonds.
(B) the octets of all atoms are complete than if
octets of all atoms are not complete.
(C) it has charge separation than if it has no
charge separation.
(D) it involves cyclic delocalization of (4n+2)π
electrons than if it involves acyclic
delocalization of (4n+2)π - electrons.
(E) it involves cyclic delocalization (4n)π –
electrons than if it involves acyclic
delocalization of (4n)π – electrons.
(F) +ve charge is on more electronegative atom if
+ve charge is on less electronegative atom.
Q 2. Select the compounds/ions in which resonance is
not possible.
(A) 4 (B) 2
(C) 6 (D) 8
Q 3. HNCO is isocyanic acid exists as following
resonating structures
The correct stability order
(A) I III II (B) I II III
(C) II III I (D) II I III
Q 4. Which of the given is least stable resonating
structure ?
(A)
(B)
(C)
(D)
Q 5. The correct stability order of the following
compounds is
(I) (II)
(III) (IV)
(A) I II III IV (B) IV I II III
(C) IV I III II (D) IV II I III
Q 6. Identify more stable canonical structure in each of
the following pairs?
(A)
C
O
H OH
C
O
H OH
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(B)
(C)
(D)
(E)
(F)
(G)
(H)
(I)
(J)
(K)
Q 7. Which of the following resonating structure of 1
– methoxy – 1,3 – butadiene is least stable?
[IIT JEE 2005S]
(A) 2 3CH CH CH CH O CH−
− = − = −
(B) 2 3CH CH CH CH O CH−
= − − = −
(C) 2 3CH CH CH CH O CH−
− − = − −
(D) 2 3CH CH CH CH O CH−
= − = − −
Q 8. Resonance energy will be more if
(A) canonical structures are equivalent than if
canonical structures are non-equivalent.
(B) canonical structures have charge separation
than if canonical structures have no charge
separation.
(C) canonical structures have more charge
separation than if canonical structures have
less charge separation.
(D) molecule is aromatic than if molecule is not
aromatic.
Q 9. Which of the following statements is (are) true
about the contribution of a canonical structure in
resonance hybrid?
(A) more stable canonical structure will have
more contribution than less stable canonical
structures.
(B) A charge separated canonical structure will
have more contribution than a canonical
structures without charge separation.
(C) A canonical structures with –ve charge on
more electronegative atom and +ve charge
on less electronegative atom will have more
contribution than a canonical structure with
+ve charge on more electronegative atom and
–ve charge on less electronegative atom.
(D) A canonical structure with more number of
bonds will have more contribution than a
canonical structure with less number of bonds.
Q 10. Assertion (A): Energy of resonance hybrid is
equal to the average of energies of all canonical
structure.
Reason (R): Resonance hybrid can’t be presented
by a single structure. [NCERT Examaplar]
(A) Both A & R are correct and R is the correct
explanation of A
(B) Both A & R is correct but R is not correct
explanation of A
(C) Both A & R are not correct
(D) A is not correct but R is correct
Q 11. Which of the following resonating structure is the
minor contribution to the real structure?
N N
CH2 CH2
R P = O 3 R P – O 3
CH 2 CH 2
C
O
H
NH
H
C
O
H
NH
O
C
CH 2 H
O
C
CH 2 H
CH – O – CH 2 3 CH =O – CH 2 3
CH – CH = CH – O 3 CH – CH – CH = O 3
CH – C = CH2 2 CH = C – CH2 2
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(A) I (B) II
(C) III (D) All of these
Q 12. Which of the following compound has both the
resonating structure contributing equal to the
resonance hybrid?
(A)
(B)
(C)
(D)
Q 13. Which of the following pairs has higher
resonance energy?
(A) CH3 COOH and CH3COONa
(B) CH2=CH-O– and CH2=CH-OH
(C)
(D)
(E) CH3 COCl and CH3 COF
(F) CH2=CH-F and CH2=CH-Br
(G)
(H)
(I)
(J)
(K)
(L)
(M)
(N) CH2=CH-OH and CH2=CH-CH=CH-OH
(O)
(P) CH2=CH-O-CH=CH2 &
CH2=CH-NH-CH=CH2
(Q) CH2=CH-NH and HN=CH-NH
(R)
Q 14. Which of the following statements is true about
the contribution of I and II in respective
resonance hybrid?
(A) Both I and II have same contributions
(B) I has more contribution than II
(C) I has less contribution than II
(D) It is not possible to analyse their relative
contribution.
Q 15. Among these molecules, the correct order of
resonance energy per ring is
(A) III>II>I (B) I>II>III
(C) I>II>III (D) II>I>III
CH = CH – CH = O CH – CH = CH – O2 2
COO
and
O
and
And CH = CH – CH2 2
And CH = CH – CH2 2
And CH = CH – CH2 2
And
OH
OH
And
And
O
And
O
And
N
AndN
H
CH = CH – O CH2 3CH – CH = O CH2 3
I
CH = CH – NH CH2 3CH – CH = NH CH2 3
II
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6. Effects of Resonance on Bond Length
Q 1. Among these compounds, the correct order of
C-N bond lengths is
(A) 4 >1 > 2 > 3 (B) 3 > 1 > 2 > 4
(C) 3 > 2 > 1 > 4 (D) 3 > 1 > 4 > 2
Q 2. Which of the following is the correct order of
C-C bond lengths among these compounds?
CH3O-CH=CH-NO2 I
CH2=CH-NO2 II
CH2=CH-OCH3 III
CH2=CH2 IV
(A) I > II > III > IV (B) IV > III > II > I
(C) I > III > II > IV (D) II > III > I > IV
Q 3. Which of the following statements would be true
about this compound?
(A) All three C-N bonds are of same length .
(B) Cl-N and C3-N bonds are of same length but
shorter than C5-N bond.
(C) Cl-N and C3-N bonds are of same length but
longer than C5-N bond.
(D) Cl-N and C3-N bonds are of different lengths
but both are longer than C5-N bond.
Q 4. In which of the given compound C-O bond length
is minimum?
(A) (B)
(C) (D)
Q 5. The correct order of increasing C-O bond length
of 23 2CO,CO ,CO−
is
(A) 23 2CO CO CO− (B) 2
2 3CO CO CO−
(C)23 2CO CO CO− (D) 2
2 3CO CO CO −
Q 6. In which of the following mulecule resonance is
isovalent?
(A) (B) CH2=CH-CH=CH2
(C) (D). None of these Q 7. In which of the following molecules – electron
density in ring is minimum?
(A) (B)
(C) (D)
Q 8. In which of the following molecules – electron
density in ring is maximum?
(A) (B)
(C) (D)
Q 9. In Pyrole
[NEET 2016 – II]
NH2
CHO
I
NH2
II
NH2
CH = NH2
III IV
13
5
O N2
BrNO2
NO2
HO
OH
OH
NH2
OH
HC OO
CHO
NO2 OCH3
NO2
H N2
NO2 O
NH2 OCH3
N
H
NO 2
NO 2
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The electron density is maximum on
(A) 2 & 3 (B) 3 & 4
(C) 2 & 4 (D) 2 & 5
Q 10. Following are the canonical structures of
naphthalene
Which of the following statements is true about
the Cl-C2 and C2-C3 bond lengths?
(A) Both bonds are of same length.
(B) Cl-C2 bond is longer than C2-C3 bond.
(C) Cl-C2 bond is shorter than C2-C3 bond.
(D) It is not possible to judge the bond lengths
because given structures are tautomers
Q 11. Which of the following statements is true about
this molecule?
2
3
4
1
(A) C1-C2 and C3-C4 bonds are of same length.
(B) C1-C2 bond is shorter than C3-C4 bond.
(C) C1-C2 bond is longer than C3-C4 bond.
(D) C1-C2 and C2-C3 bonds are of same length.
Q 12. The order of the C-O bond lengths among these
compounds is
NO2
OHOHOH
NO2I II III
(A) I > II > III (B) III > II > I
(C) II > I > III (D) III > I > II
Q 13. Which of the following compounds do not have
all C-C bonds of same length?
A)
B)
+C)
_D)
Q 14. Among the following compounds which has
longer C-O bonds?
O
CH HA)
O
CHB) F O
CHC) NH2
O
CHD) OH Q 15. In the anion HCOO – the two carbon – oxygen
Bonds are formed of equal length. What is the
reason for it. [AIEEE 2003]
(A) The C=O bond is weaker than C – O bond
(B) The anion HCOO– has 2 resonating structure.
(C) The anion is obtained by removal of a proton
from the acid molecule
(D) Electronic orbitals of carbon atom are
hybridiesed
7. Resonance Energy, Effect of Resonance
Q 1. The stability order of these canonical structures is
(A) I > II > III (B) II > III > I
(C) I > III > II (D) III > I > II
Q 2. The most stable canonical structures of this
molecule is
(A) (B)
(C) (D)
12
34
2
3
1
4
2
3
1
CH – C – N3
OHCH3
CH3
CH – C – N3
OHCH3
CH3
CH – C – N3
OHCH3
CH3
I II III
N
N
N
N
N
N
N
N
N
N
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Q 3. Among the following, the least stable resonance
structures is
(A)
(B)
(C)
(D)
Q 4. Which of the following canonical structures is
least stable?
(A) I (B) II
(C) III (D) both II&III.
Q 5. The correct stability order of the following
resonance structure is
(I) 2H C N N+ −
= = (II) 2H C N N+ −
− =
(III) 2H C N N− +
− (IV) 2H C N N− +
− =
(A) I II IV III (B) I III II IV
(C) II I III IV (D) III I IV II
Q 6. A highly important canonical structure of this
molecule is
(A) (B)
(C) (D)
Q 7. Which of the following pairs of compounds has
greater resonance energy?
(A)
(B)
(C) (D)
Q 8. Resonance energies of these cations are in the
order
(A) II > I > III (B) I > II > III
(C) III > II > I (D) III > I > II
Q 9. Resonance energies of these compounds are in
the order as
N = O
O
N = O
O
N = O
O
N – O
O
N|
H I
N|
HII
N|
H
III
O
O
O
O
OI
II
Or
N|
H
O Or O
Or
CH2
N|
HI
II III
O
Or
CH 2 +
O
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(A) I > III > II (B) III > II > I
(C) II > I > III (D) III > I > II
Q 10. Among these compounds what is the order of the
resonance energies?
(A) III > IV > I > II (B) III > IV > II > I
(C) II > I > IV > III (D) I > II > IV > III
Q 11. Which of the following choice is the correct order
of resonance energy of these molecule?
(A) I > II > III (B) III > II > I
(C) II > I > III (D) III > I > II
Q 12. Which of the following choice is the order of
resonance energy of these radicals?
(A) I > II > III (B) I > III > II
(C) III >I > II (D) III > II > I
Q 13. In the following molecule, the correct order of
heat of hydrogenation is
(A) IV III II I (B) IV III II I
(C) II IV I III (D) II IV III I
Q 14. Heat of hydrogenation.
(I) -28.6 k cal/mole
(II) -55.5k cal/mole
(III)-49.8k cal/mole
As shown above, heat of hydrogenation of II is
more than that of I. But heat of Hydrogenation of
III is less than that of II. Suggest a suitable
explanation. Based on these Heats of
hydrogenation what will be the correct order of
their stability:
(A) I > II > III (B) II > I > III
(C) II > III > I (D) I > III > II
Q 15. Among the following pairs identify the one which
gives higher heat of hyderogenation?
(A)
(B)
(C) 2 2CH CH CH CH= − = and
3 3CH CH CH CH− = −
(D)
(E)
(F)
Q 16. In which of the following pairs, indicated bond is
of greater strength?
(A)
(B)
(C)
(D)
OH
I II III
N
I II IIIIV
I II III
I
CH2
CH = CH – CH2 2
II
CH = CH – CH – CH = CH2 2
III
OCH3 OCH3
I II
OCH3 OCH3
III IV
CH2CH3
CH2
And
CH2CH3
CH3
CH2CH3
CH3
And
CH2CH3
CH3
C = C CH3
H
H
CH3
And C = C CH3
H H
CH3
CH = CH – CH2
CH3
CH3
And CH = C2
CH3
CH – CH2 3
CH2
CH2
And
CH3
CH2
C
O
CH3
C1
And CH – CH – C13 2
CH C – C CH and CH = CH – CH = CH 2 2
CH – C CH and HC CH3
C
O
H N2 NH2
AndC
O
CH3 NH2
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(E)
8. Introduction to Aromaticity
Q 1. Select the compounds/ions which are aromatic
anti-aromatic and non –aromatic seperately
1. 2. 3.
4. 5. 6.
7. 8. 9.
10. 11. 12.
13. 14. 15.
16. 17.
18. 19. 20.
21. 22.
23. 24.
25. 26.
27. 28.
29. 30.
31. 32.
33. 34.
Q 2. Which of the given is most stable carbonium ion
(A) (B)
(C) (D)
Q 3. Which of the given is most stable carbanion
(A) (B)
(C) (D)
Q 4. The most polar compound is
(A) (B)
(C) (D)
Q 5. Which of the given is not polar
N
O
O
N|
H O
O
NH
O
BO
B
OB
CH3
H C3 CH3
S
O
HN
H–B
B – CH3
B – CH3
O SiH
HH C–B3 Si
H
H
S
N: N:
N:
CH2
CH2
CH
CH 2 CH 3
And
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(A) (B)
(C) (D)
Q 6. Rotation about indicated bonds is easiest in which
of these molecules?
(A) I (B) II (C) III (D) IV
Q 7. In which of the given axial rotation barrier along
C C= between two rings follows the correct
order is
(I) (II) (III)
(A) I II III (B) II III I
(C) III I II (D) II I III
Q 8. Total number of delocalized electrons in the
given compound is
(A) 16 (B) 12
(C) 18 (D) 20
Q 9. Which of the following is a non – aromatic
compound / species?
(A) (B)
(C) (D)
(A) A (B) B
(C) C (D) D
Q 10. The compound which cannot rearranged into an
aromatic compound is
(A) (B)
(C) (D)
Q 11. For the benzyne correct statement is
(A) Four carbon atom is 2sp and 2 carbon
atom is sp hybridized
(B) All the carbon is sp hybridized
(C) All the carbon is 2sp hybridized
(D) None of these
Q 12. For the benzyne correct statement is
(A) the Pi bond formed outside the ring between
P orbitals
(B) The pi bond formed outside the ring is in
between SP2 orbitals
(C) 2 carbon atoms are SP Hybridised
(D) None of these
Q 13. Stability order of these compounds is in the order
(A) I > II > III (B) I > III > II
(C) III > I > II (D) II > I > III
Q 14. Which of the following compounds is not
aromatic?
Q 15. The correct stability order of the given molecule
is
I
II CH2 = CH2
III
HC CH
IV
N:
O: :
NH:
N
:
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(A) II III I IV (B) II III IV I
(C) I II III IV (D) II I III IV
9. Aromatisation Reaction & U.F. Factor
Q 1. Which produces aromatic species in each of the
following reactions?
(A)
(B)
(C)
(D)
(E)
(F)
Q 2. The ease of ionization of these compounds to
produce Br is in the order as:
(A) I > II > III (B) III > I > II
(C) II > III > I (D) III > II > I
Q 3. The order of the ease of ionization of these
compounds to produce carbocations and Br– is
(A) I > III > II (B) II > I > III
(C) I > III > II (D) III > II > I
Q 4. Ease of ionization to produce carbocation and
Bromide will be maximum in which of the
following compounds
(A) (B)
(C) (D)
Q 5. Which of the following statements is true about
this molecule (furan))?
(A) Both lone-pair of electrons are in sp3 orbitals.
(B) Both lone-pair of electrons are in sp2 orbitals.
(C) Both lone-pair of electrons are in Pz orbitals.
(D) One lone pair of electrons in sp2 orbital while the
other is in Pz.
Q 6. Lone pair of pyridine (C6H5N), is in
(A) p- orbital (B) sp3- orbital
(C) sp2- orbital (D) sp- orbital
Q 7. Calculate hydrogen deficiency index
(unsaturation factor) in each of the following
molecular Formula
(A) C14H12N2O2Cl2 (B) C2H8N2
(C) CH3 radical (D) (C3H5)
(E) (C5H5) (F) (C7H8NO)
(G) C6H5Cl (H) C2HO2Na
Q 8. What is the unsaturation factor in each of the
following compounds?
(A) 3CH CN (B) 3CH COOH
(C) (D)
(E) (F)
(G)
III IV
K?
HClO4?
Na?
CH2
O
NaH?
O Br O
I II
Br N
CH3
Br
III
H
I BrH
II
H
III
Br
BrBr
Br
CH O3 Br
O
::
CHO
Buli ?
O HClO 4
?
I II
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Q 9. If unsaturation factor of a molecule is 2. If
implies that molecule has
(A) two dausle bonds (B) one triple bond
(C) two cyclic structure (D) All of these
Q 10. Unsaturation factor can’t have
(A) fractional value (B) zero value
(C) –ve value (D) All are possible
Q 11. Find no of hemolytic cyclic structure possible
from the formula 4 8C H O
(A) 4 (B) 5
(C) 6 (D) 3
Q 12. Find number of carbonyl compounds possible
from the molecular formula 4 8C H O
(A) 3 (B) 4
(C) 5 (D) 6
Q 13. Find number of structural isomers possible from
molecules formula 4 8C H
(A) 4 (B) 6
(C) 8 (D) 5
Q 14. Find number of two cyclic structures possible
from molecular formula 5 8C H
(A) 4 (C) 3
(C) 5 (D) 6
Q 15. Find number of Amide structure possible from
the molecular formula 4 9C H NO
(A) 6 (B) 8
(C) 10 (D) 5
Q 16. Find the number of benzene ring structure
possible from the molecular formula 9 12C H
(A) 8 (B) 7
(C) 6 (D) 10
Answer Key 1. Hybridisation in Organic Chemistry
(1). B (2). C (3). D
(4). C (5). D (6). A
(7). B (8). D (9). D
(10). B (11). B (12). A
(13). C (14). A (15). C
(16). D (17). B (18). C
(19). D (20). C
2. Characteristics of Hybridisation
(1). A (2). C (3). C
(4). D (5). B (6). D
(7). C (8). C (9). C
(10). D (11). A (12). B
(13). A (14). C (15). C
(16). B (17). A
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(18).
No of Pi Bonds Hybridisation of C, N & O
0 SP3
1 SP2
2 SP
(19). A, E, F, I, K (20). A, B, D, E, I, J, K
(21). 18, 6, 42, 3, 15, 12
3. Resonance
(1). D (2). A, B, D (3). B
(4). D (5). B (6). D
(7). B (8). B
(9). D, G, H, I, J
(10). See the Notes
(11). Donar – B, C, E, F, G, H, I, J
Acceptor – A, B, C, D, F, G, H, I, J
(12). A, B, C, E +ve charge Only, G, I J, N
(13). C
4. Drawing Resonating Structure
(1). A (2). A (3). B
(4). D (5). D (6). C
(7). C (8). D (9). D
(10). D (11). C (12). B
(13). B (14). A
5. Stability of Resonating Structures
(1). A, B, D (2). A (3). A
(4). A (5). C
(6). A – 1, B – Equal, C – 1. D – 1, E – 1, F – 2,
G – 2, H – 1, I – 1, J – 2, K – 2
(7). C (8). A, D (9). A, C, D
(10). D (11). B (12). C
(13). A – 2, B – 1, C – 2, D – 2, E – 2, F -1, G –
2, H – 2, I -1, J – 2, K – 2, L – 1, M – 2, N – 2, O
-2, P – 2, Q – 2, R – 2
(14). C (15). C
6. Effects of Resonance on Bond Length
(1). C (2). A (3). C
(4). C (5). D (6). A
(7). D (8). B (9). D
(10). C (11). B (12). B
(13). B (14). C (15). D
7. Resonance Energy, Effect of Resonance
(1). D (2). A (3). B
(4). B (5). B (6). B
(7). A – II, B – I , C – I , D – I
(8). A (9). D (10). B
(11). A (12). B
(13). C (14). D
(15). A – I, B – I, C – I, D – I
(16). A – 1, B – I, C – 2, D – 2, E – 2
8. Introduction to Aromaticity
(1). Aromatic : 1, 2, 3, 5, 7, 8, 9, 11, 14, 15, 16,
17, 18, 21, 22, 25, 27, 31, 32, 33, 34
Non-aromatic : 4, 6, 13, 19, 30
Anti – aromatic: 10, 12, 23, 24, 26, 28
(2). B (3). B (4). D
(5). A (6). A (7). D
(8). B (9). D (10). D
(11). C (12). B (13). A
(14). D (15). C
9. Aromatisation Reaction & U.F. Factor
(1). All (2). B (3). A
(4). A (5). D (6). C
(7). (A) 9 (B) 0 (C) 1/2 (D) 3/2
(E) 7/2 (F) 9/2 (G) 4 (H) 2
(8). A – 2, B – 1, C – 4, D – 2, E – 4, F – 5, G – 3
(9). D (10). C (11). B
(12). A (13). D (14). C
(15). B (16). A