ANDHERI / BORIVALI / DADAR / CHEMBUR / THANE / MULUND/ NERUL / POWAI

IIT JEE: 2016 CRASH COURSE (C 7 A 2) DATE:

TOPIC: IUPAC, NOMENCLATURE, GOC

Paragraph 1:
The IUPAC nomenclature of organic chemistry is a systematic method of naming organic chemical
compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC).
Ideally , every possible organic compound should have a name from which an unambiguous
structural formula can be created.
For ordinary communication, to spare a tedious description, the official IUPAC naming
recommendations are not always followed in practice, except when it is necessary to given an
unambiguous and absolute definition to a compound, or when the IUPAC name is similar (e.g.
ethanol instead of ethyl alcohol). Otherwise the common or trivial name may be used, often derived
from the source of the compound (see below). In addition, very long names may be less concise than
structural formulae.

1. Correct IUPAC name of the given following compound

F
OH
N

O O

(A) 4 - cyano- 2 - fluoro- 3 - oxobutanoic acid

(B) 4 - carboxy- 4 - fluoro- 3 - oxobutanenitrite
(C) 5 - cyano- 2 - fluoro- 3 - oxo pentanoic acid
(D) 4 - fluoro- 5 - hydroxy- 3,5 - dioxopenutanenitrites

2. How many types of functional group present in the compound

O OH
Cl

Cl OH

O
O
(A) 6 (B) 4 (C) 5 (D) 7

3. Correct order of seniority order of functional group

O

(A) (B)

(C) (D)

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA # 1

Paragraph -2
In chemistry, resonance or mesomerism is a way of describing delocalized electrons within certain
molecules or polyatomic ion where the bonding cannot be expressed by one single Lewis formula. A
molecule or iron with such delocalized electrons is represented by several contributing structures
(also called resonance structures or canonical forms.
Each contributing structure can be represented by a Lewis structures, with only an integer number of
covalent bonds between each pair of atoms within the structure. Several Lewis structures are used
collectively to describe the actual molecular structure. Which is an approximate intermediate
between canonical forms called a resonance hybrid. Contributing structures differ only in the
position of electrons, not in the position of nuclei?

4. Which of the following compound will be resonance stabilized?

O O N O
(A) (B) (C) (D)

5. Which of the following is a pair of resonance structures?

+
+

+ O OH
(A) (B)

+ +

(C) (D)

6. Find out the which order is correct for resonance energy

(A) (B) N

<
N S

(C) H (D)

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA # 2

Paragraph-3
The other effect if based on the premise that an ortho-substituted acid (take benzoic acid as an example) is
more acidic than the metal or para- substituted form. this effect is not dependent on the nature of the
substituent ( e-donating or e- withdrawing ). The reason for this is that the steric hinderance between the
substituent and the neighboring carboxylate forces the carboxylate to bend out of the plane of the aromatic
ring. This conformational shift alters the delocalization of the charge into the benzene ring, making it easier
for the negative charge to be delocalized throughout the pi-system.

7. The decreasing order of acidity (Ka) order

O OH
O

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

8. Which of the following compound is strongest acidic

COOH

N N N
O O O O
(A) (B) (C) (D)

9. The correct order of acidity of the compounds P R is

O
O HO O

HO O
O O

(A) P > Q > R (B) Q > R > P (C) R > P > Q (D) Q > P > R

Paragraph 4
According to the Lowry-Bronsted definition an acid is a substance that gives up a proton, and a base is a
substance that accepts a proton. In a given acid base reaction formation of weaker acid is favourable.

10. Which of the following is strong acid?

OH CO2H
O2N NO 2
OH CO2H
NO 2

(A) (B) (c) NO 2 (D) OCH3

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA # 3

11. Select the correct statements
(i) Acetic acid is soluble in NaHCO3 solution
(ii) Phenol is soluble in Na 2 CO3 but insoluble in NaHCO3
HO O

(iii) HO O is soluble in NaOH and NaHCO 3 solution

(A) i, ii only (B) i, iii only (C) ii, iii only (D) i, ii, iii

12. Find out the correct statement about given reaction

(A) Reaction favours to product formation

(B) (1) is the strongest acid
(C) (2) is the strongest base
(D) All of these

Paragraph 5
Electron delocalization lowers the potential energy of the substance and thus makes it more stable
than any of the contributing structures. The difference between the potential energy of the actual
structure and that of the contributing structure with the lowest potential energy is called the
resonance energy or delocalization energy.

13. The decreasing order of the resonance energy is:

S N
H N

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

14. N

(i) Total number of degree of unsaturation value = x

(ii) Total number of atom having localized lone pair = y
(iii) Total no. of resonance stabilized anion after deprotonation = z
(A) 10 (B) 8 (C) 7 (D) 9

15. Which of the following readily undergo hydrogenation

(A) (B) (C) (D) All of these

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA # 4

Paragraph 6
Basicity, You will recall that the nitrogen atom of ammonia is sp3 hybridized and there is an unstread pair of
electrons in the fourth tetrahedral orbital. This makes ammonia base and a nucleophile. Because nitrogen is
less electronegative than oxygen ammonia is a much stronger base than water and also a much better
nucleophile. Amines, which are merely organic derivatives of ammonia are also tetrahedrally hybridized and
are comparably basic and nucleophilic to ammonia. You might recall that amines are completely neutralized
(prevented) by carboxylic acids.

16. Pyrrole is less basic than pyridine. The orbital having the lone pair of electrons on nitrogen in pyrrole
is
(A) S orbital (B) P orbital (C) Sp 2 (D) Sp3

17. The increasing order of basicity among the following is:

(A) y < x < z (B) y < z < x (C) x < z < y (D) x < y < z

18. Order of basic strength

NH NH NH
NH

HN NH HN O HN

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

Paragraph 7
The electron cloud in a bond between two unlike atoms is not uniform and is slightly displaced
towards the more electronegative of the two atoms. This causes a permanent state of bond
polarization, where the more electronegative atom has a slight negative charge ( ) and the other
atom has a slight positive charge ( + ) . If the electronegative atom is then joined to a chain of
atoms, usually carbon, the positive charge is relayed to the other atoms in the chain. This is the
electron-withdrawing inductive effect, also known as the I effect. Some groups such as the alkyl
group, are less electron- withdrawing than hydrogen and are therefore considered as electron
releasing. This is electron releasing character and is indicated by the + I effect. In short, alkyl
groups tend to give electrons, leading to induction effect.
As the induced change in polarity is less than the original polarity, the inductive effect rapidly dies
out and is significant only over a short distance. Moreover, the inductive effect is permanent but
feeble since it involves the shift of strongly held bond electrons and other stronger factors may
obvershadow this effect.

19. The I effect of N Me3 , COCl, NO 2 , SO3 H decreases in the order
+ +
(A) NO 2 > N Me3 > COCl SO3 H (B) N Me3 > NO 2 > SO3 H > COCl
+ +
(C) N Me3 > SO3 H > NO 2 > COCl (D) SO3 H > NO 2 > N Me3 > COCl

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA # 5

20. Find out the acidic strength order:
I: CHF2 CH 2 CO 2 H II: CH 3CF2 CH 2 CO 2 H
III: CH 3CH 2 CF2 CO 2 H IV: CH 3CH 2 CH 2 CO 2 H
(A) I > II > III > IV (B) I > IV > III > II (C) III > II > I > IV (D) IV > I > II > III

21. Find out the correct order stability

Me

Me Si
>
(A) (B)

+
+

(C) (D)

Paragraph 8
The German chemist Erich Huckel was the first to recognize that an aromatic compound must have an odd
number of pairs of electrons. In 1931 he described this requirement by what has come to be known as
Huckels rule, or the 4n + 2 rule. The rule states that for a planar, cyclic compound to be aromatic , its
uninterrupted cloud must contain ( 4n + 2 ) electrons, when n is any whole number.

22. Which one is the aromatic compound

(A) Cyclotheptatrienyl cation (B)

O

(C) (D)

23. Amongst the following compounds the one that is non-aromatic, is

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

24. The compound that gives precipitate on warming with aqueous AgNO3 is
Br Br
Br
Br

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

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA # 6

Paragraph 9
Hyperconjugation is the stabilising interaction that results from the interaction of the electrons in a
bond usually C H or C C ) with an adjacent empty or partially filled p-orbital or a orbital
to given extended molecular orbitals that increases the stability of the system

25. The correct order of heat of hydrogenation for the following compounds is

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

26. Find out the stability order of the given following carbocation intermediate

+ +
+

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

+
27. Which one is more stable than
+

+
(A) MeO (B) (C) (D) All of these

Paragraph (Resonance effect 10)

The resonance of feet involves delocalization of electrons- typically, those called ( pi ) electrons. It
depends upon the overlap of certain orbitals, and therefore can only operate when the substituent is
located in certain special ways relative to the charge centre. By its very nature, the resonance effect
is a stabilising effect, and so it amounts to electron withdrawal from a negatively charge center and
electron release to a positively charged centre

28. Which one is the most stable carbocation

+ +

(A) O (B)
+ N

(C) (D)

29. In which of the following resonance effect is not observed

+

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

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA # 7

30. Find out the order of stability of carbanion.

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

Matrix Match

31.
Column-I Column-II
OH
(P) Aromatic

(A)
N
(Q) Anti aromatic
(B) N

(R) Non aromatic

(C)
+
(S) Reaction with Na to evolve H 2 gas

(D) O
(T) undergo dimerization

32.
Column-I Column-II
+ (P) + I
(A) N H3
(B) N = O (Q) I
(C) NO 2 (R) + M
(D) ONa (S) M

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA # 8

33.
Column-I Column-II
(A) 1,5 dimethyl cyclobhexa-1,3-
diene

(P)
(B) 2,5 dimethyl cyclohexa-1,3-diene

(Q)
(C) 1,6 dimethyl cyclohexa-1,3-diene

(R)
(D) 2, 6 dimethyl cyclohexa-1,3-diene

(S)

34.
Column-I Column-II
(P) (A) Aromatic

(B) Anti aromatic

N
(Q)
(C) undergo dimerization

N
(R)
(D) Non aromatic

(S)

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA # 9

35.
Column-I Column-II
(P) Aromatic compound
+
+
(A)
(Q) Non aromatic compound

(B)
(R) Planar

(C)
(S) Non-Planar
O

(D)

36.
Column-I Column-II (pKa of conjugate acid)
(P) 7.05
Cl

(A)
(Q) 8.75

(B)
N (R) 8.92
N
(C) H
(S) 9.85

(D) N

37.
Column-I Column-II
2
(P) Sp Hybridization

(A)
(Q) Paramagnetic

(B)
(R) Diamagnetic
(C)
(S) Sp3 hybridization

(D)

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA # 10

38.
Column-I Column-II
Br (P) 3 Bromo 3 chloro cyclopropene

(A) Cl

(Q) 3 Bromo 1 chloro cyclopropene

Cl Br
(B)
(R) 1 Bromo 2 chloro cyclopropene

Br
(C) Cl

(S) 1 Bromo 3 chloro cyclopropene

Br

(D) Cl

39.
Column-I Column-II
N
O (P) Resonance
O

(A)
(Q) Hyperconjugation

(B)
(R) Inductive effect

O
(C)
F
(S) M effect of gp
(D)

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA # 11

 ANDHERI / BORIVALI / DADAR / CHEMBUR / THANE / MULUND/ NERUL / POWAI
IIT JEE: 2016 CRASH COURSE (C 7 A 2) DATE:
TOPIC: IUPAC, NOMENCLATURE, GOC

ANSWER KEY

1. (A) 2. (C) 3. (D) 4. (A) 5. (A)

6. (C) 7. (C) 8. (C) 9. (C) 10. (C)

11. (D) 12. (D) 13. (D) 14. (A) 15. (B)

16. (C) 17. (C) 18. (B) 19. (C) 20. (C)

21. (B) 22. (A) 23. (D) 24. (C) 25. (B)

26. (C) 27. (A) 28. (A) 29. (C) 30. (B)

31. (A) P, S; (B) Q, T; (C) R; (D) P

32. (A) Q; (B) Q, R, S; (C) Q, S; (D) P, R

33. (P) C; (Q) D; (R) A; (S) B

34. (P) B, C; (Q) B; (R) A; (S) A, C

35. (A) P, R; (B) P, R; (C) Q, S; (D) Q, S

36. (A) P; (B) Q; (C) S; (D) R

37. (A) P, R; (B) P,Q; (C) P, R, S; (D) P, R

38. (A) R; (B) S; (C) Q; (D) P

39. (A) P, Q, R, S; (B) Q; (C) P, R, S; (D) R

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA # 12