Fiitjee: Subject: Chemistry Alkyl Halide Aryle

FIITJEE
SUBJECT: CHEMISTRY ALKYL HALIDE ARYLE
NAME…………………….. ENROLL NO……………. BATCH…………………
SECTION-I (ONLY ONE CORRECT)

1. What will be the correct order of rate of solvolysis of the following alkyl chlorides in 50% aqueous
ethanol at 44.6C?
(A) II > III > I (B) III > I > II

(C) I > III > II (D) III > II > I
(Rate of solvolysis is directly proportional to stability of carbocation).
2. In the following compounds, the order decreasing reactivity
of different chlorine atom towards NaSH is no aqueous
solvent is
(A) i > iv > ii > iii
(B) iv > i > iii > ii
(C) i > iv > iii > ii
(D) iii > ii > iv > i
3. What is the correct order of SN1 reactivity of the following alkyl halide?
C6H5 CH2 Br,C6H5 CH  C6H5  Br, C6H5 CH  CH3  Br,C6H5 C  CH3   C6H5  Br
1  2  3  4
(A) 4 > 2 > 3 > 1 (B) 4 > 3 > 2 > 1
(C) 4 > 2 > 1 > 3 (D) 2 > 3 > 4 > 1
4. Choose the incorrect statement
(A) Among dichloro benzenes, para dichloro benzene has highest melting point
(B) Boiling point of isomeric haloalkanes decreases with increase in branching
(C) One molecule of DDT contain five atoms of chlorine
(D) Chloroform is slowly oxidised by air in the presence of light to form methanol
5. For the given reaction,
Which substance will give maximum racemisation?
(A) (B)
(C) (D)
6. Pyrrol + Phenyl magnesium bromide  E + F

E + Methyl chloride  G + H
F + Methylchloride  no reaction without a catalyst
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The structure of the products (E) to (H) respectively are

(A) 3, 2, 6, 7 (B) 4, 5, 6, 1
(C) 2, 3, 4, 5 (D) 3, 2, 4, 5
7. The major product obtained in the following reaction will be
(A) (B)
(C) (D)
8. In the cyclization reaction given below, the most probable product of the reaction
(A) (B)
(C) (D)
9. In the reaction
Product P; should
(A) (B)
(C) (D)
FIITJEE
(A) (B)
(C) (D)
11.
(A) (B)
(C) (D)
12.
(A) (B)
(C) (D)
13.
FIITJEE
(A) (B)
(C) (D)
14 The relative rates of chlorination at various positions in 1-Flurobutane are
(A) 3 > 1 > 2 > 4 (B) 2 > 3 > 1 > 4

(C) 3 > 2 > 4 > 1 (D) 3 > 2 > 1 > 4
15. What is the correct order of SN1 reactivity of the following alkyl halide?
C6H5 CH2 Br,C6H5 CH  C6H5  Br, C6H5 CH  CH3  Br,C6H5 C  CH3   C6H5  Br
1  2  3  4
(A) 4 > 2 > 3 > 1 (B) 4 > 3 > 2 > 1
(C) 4 > 2 > 1 > 3 (D) 2 > 3 > 4 > 1
16. Pyrrol + Phenyl magnesium bromide  E + F

E + Methyl chloride  G + H
F + Methylchloride  no reaction without a catalyst
The structure of the products (E) to (H) respectively are

(A) 3, 2, 6, 7 (B) 4, 5, 6, 1
(C) 2, 3, 4, 5 (D) 3, 2, 4, 5
17. The major product obtained in the following reaction will be
(A) (B)
(C) (D)
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18. R   MeCH I Et  131I  MeCH I Et containing some I131
obs  15.9 obs  15.26
How much of the compound has undergone racemisation?
(A) 50% (B) 10%
(C) 4% (D) 6%
Thus, 4% of the iodide is reacemized.
19. The number of structural isomers obtained on monochlorination of 2-methylbutane is “x” and out
of them the number of optically active compounds are “y”. The numbers “x” and “y” respectively
are
(A) 4, 4 (B) 5, 2
(C) 4, 2 (D) 5, 3
(A) (B)
(C) (D)
21. In the reaction
Product P; should
(A) (B)
(C) (D)
22. Some allylic carbocations are prepared as follows



(a) C  C  C 
H
C  CC


(b) C  C  C  C 
H
C  C  C C
(c)


(d) C  C  C 
H
C  C C
What is the correct order of stability of the above carbocations?
(A) a = b < c < d (B) c > a = b > d
(C) c > a > b > d (D) c > b > a > d
23. 3,5-dimethylcyclopentene reacts with N-bromo succinimide (NBS) in CCl4 in presence of

light. Identify the expected product(s) out of the given pairs.
The compound (C) would
FIITJEE
(A) (B)
(C) (D)
24.
(A) (B)
(C) (D)
25. Consider the following substarates:
The correct order of reactivity towards SN2 would be

(A) I < II < III < IV (B) II < III < I < IV
(C) IV < III < I < II (D) II < I < III < IV
26. R  O  Na  R X   R  O  R  NaX
Choose incorrect statement regarding the above reaction
(A) It is a nucleophilic substitution bimolecular reaction
(B) The alkoxide of Na may be primary, secondary or tertiary
(C) The alkyl halide should be primary
(D) It is used to prepare only symmetrical ethers
(A) A (B) B
(C) C (D) D
27. Which of the following statements is false

(A) Bridgehead halides are inert towards both SN1 and SN 2 reaction
(B) The first step in both SN1 and E1 reactions is the same
(C) SN 2 reaction is favoured by weak nucleophile and protic solvent
(D) E2 eliminations are favoured by the use of a solvent of low polarity and high
concentration of a strong base
28. Which of the following statements is correct, when tertiary butyl bromine is allowed to react with
sodium methoxide in a mixture of methanol and water?
With increase in concentration of sodium methoxide:
(A) The rate of formation of methyl ter-butyl ether increase
(B) The rate of formation of methyl ter-butyl ether increases
(C) The rate of disappearance of ter-butyl bromide increases
(D) All the above
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29.
(A) product (A) and (B) both are aromatic, although (A) is very less stable
(B) product (A) can give Diels-Alder reaction
(C) product (B) is a mixture of two structural isomers
(D) All are correct
30.
A can be
(A) (B)
(C) (D)
31. Br

Mg
ether
  A  
cyclopentadienone
P  ; The product P  is
Br
(A) (B)
O
(C) (D) O
32. Select the incorrect statement about Grignard reagent

(A) It may be made from primary, secondary and tertiary alkyl halides
(B) It cannot be made from vinyl halide
(C) Reactivity follows the order R –I > R – Br > R – Cl > R – F
(D) These are strong nucleophiles and strong bases
33. Which cannot undergo E2 reaction

(A) (B)
(D)
(C)
FIITJEE
34.
This is called
(A) Hoffmann elimination (B) Cope reaction

(C) Saytzeff reaction (D) Carbyl amine reaction
35. Periodic acid splits glucose and fructose into formic acid and formaldehyde. Ratio of moles of
formic acid and formaldehyde in glucose and fructose per mole is
(A) 5/1 and 3/2 (B) 5/1 and 5/1
(C) 4/2 and 4/2 (D) 5/1 and 4/2
SECTION-II (ONE OR MORE THAN ONE)

1. Which of the following undergo substitution by NH2  NH3 ?
(A) (B)
(C) (D)
2. During the chlorination of 3–chloronitrobenzene the possible product(s) is/are

(A) Cl (B) NO2
Cl
Cl
Cl
Cl
(C) NO2 (D) NO2
Cl
Cl Cl Cl
SECTION-III (REASONING)
1. STATEMENT-1: Ph  O  CH2  CH2  Cl in a typical hydrolysis reaction with water gives
2
Ph  O  CH2  CH2  OH , give 5  10 times faster reaction than hydrolysis of
Ph  S  CH2  CH2  Cl
and
STATEMENT-2: S-atom is better nucleophile than O-atom.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for
Statement-1
(B) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for
Statement-1.
(C) Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True
FIITJEE
2. STATEMENT-1: Ph  O  CH2  CH2  Cl in a typical hydrolysis reaction with water gives
2
Ph  O  CH2  CH2  OH , give 5  10 times faster reaction than hydrolysis of
Ph  S  CH2  CH2  Cl
and
STATEMENT-2: S-atom is better nucleophile than O-atom.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for
Statement-1
(B) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for
Statement-1.
(C) Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True
SECTION-IV (PARAGRAPH)
The high potential quinine, 2,3-dichloro-5, 6dicyanobenzoquinone (DDQ), is a powerful dehydrogenating
agent. Initially it was used for the dehydrogenation of hydroaromatic compounds. Later its use was
extended to the steroid field. Reaction with DDQ may be carried out in the inert solvents such as benzene,
toluene dioxane. THF, but dioxane and hydrocarbon solvents are often preferred, because DDQH2 formed
in these solvents in insoluble and can be removed by filtration.
1. What will be the major product formed in the reaction given below?
(A) (B)
(C) (D)
1. C
2 What will be the major product of the following reaction
(A) (B)
(C) (D)
FIITJEE
PARAGRAPH-II
The preparation, isolation, and characterization of highly unstable compounds remain a challenge for
synthetic organic chemists. To circumvent these problems, chemists have developed the method of
matrix isolation, which typically involves trapping an unstable compound by freezing. Compounds isolated
by this technique are benzyne and a propellane
Benzyne
Benzyne is highly unstable intermediates that is thought to be formed from the base promoted elimination
of a halide and a hydrogen from adjacent carbon atoms in an aryl halide. It has been proposed that the
structure of benzyne is highly strained and contains a very reactive triple bond. Although benzyne cannot
be routinely isolated, evidence for the existence of this intermediates has been provided by the isolation of
its decomposition by product, triphynylene, which is presumably formed from a reaction between three
molecules of benzyne. In adition, benzyne can now be trapped (and detected spectroscopically) by the
photochemical decomposition of a high energy reactant in a frozen argon matrix
Propellanes are extremely reactive compound in which two carbons that are directly connected are also
connected by three other bridges. The propellant shown in Reaction 2 readily reacts with itself to form the
corresponding dimer
Under controlled reaction conditions, however, this propellane can be isolated. As shown in Reaction 3,
when the dillodo compound is treated with potassium at relatively high temperatures, the resulting
propellane may be trapped by rapidly freezing the vapour into a nitrogen matrix.
4. Which of the following represents a resonance structure of benzyne?

(A) (B)
(C) (D)
FIITJEE
5. According to the passage, the solid matrix in which an unstable compound is to be trapped should
(A) be composed of a substance with a high freezing point
(B) be composed of a substance with a low freezing point
(C) react with the starting material to give the unstable product
(D) react with the unstable product to give a new, stable product
6. In addition to benzyne, which of the following compounds will most likely be formed in the
reaction?
(A) 4O2 (B) 2CO (C) 2CO2 (D) H2 CO3
Paragraph-III
Consider the following reactions:
Similar reaction occurs with  CH3 2 SO DMSO  and the difference between  CH3 2 S and  CH3 2 SO is
the dimethylsulphonium methylid (I) adds to ketone irreversibly whereas the addition of
dimethylsulphoxonium methylid (II) of DMSO (corresponding to I of  CH3 2 S is reversible. Therefore , -
unsatured carbonyl compounds when treated with II yields stable product (in which carbonyl group i s
retained) finally.
7.
The major product (IV) is
(A) (B)
(C) (D)
8.
The major product (V) is

(A) (B)
FIITJEE
(C) (D)
Paragraph-IV
In case of alkanes anticonformers are more stable than Gauche and other conformations. However, in
case of the groups at adjacent positions, strong van der Waal forces of attraction or hydrogen bonding are
more stabilized in Gauche form instead of anti form. In E2 reactions anti elimination occurs while in E1 &
E1cB it is not necessary.
9. In the following reation which ‘H’ elimates preferentially from alkyl fluoride?
(A) Ha (B) Hb
(C) Hc (D) Hd
Paragraph-V
Both the C  H and C  X bonds are breaking the the transition state of E2 reactions. The rate of E2
reactions is of second order. The rate shows primary isotopic effect. The rate is also correlated with
nucleofugality. i.e ability of leaving group to leave. This element effect is also observed in E1Cb reaction
K
in which the second step is rate determining. For E1Cb H  1 while in E1 reaction only nucleofuge
KD
departs in slow step.
10. For the given compound I and II the rate of elimination in presence of EtO EtOH shows
KH
 7.1 . What is true about this reaction?
KD
(A) Only H (or D ) is eliminated in the rate determining step

(B) Only Br  is eliminated in rate determining step
(C) Both C – H (D) and C – Br bonds are breaking simultaneously in transition state
(D) The reaction intermediate is resonance stabilized
11. KH
Observe the given reaction. In this reaction,  1. Identify the incorrect about this reaction.
KD
(A)
The nucleofuge is
(B)
The product is
(C) In EtO EtOH H- exchange will be observed
(D) In EtO EtOH the rate of reaction will be faster as compared to EtO EtOD
FIITJEE
12. Consider the following statement, “In 80% aqueous ethanol, t-butyl iodinate solvolysis 100 times
as rapidly as t-butyl chloride, but the ratio of elimination to substitution product is the same for
chloride and iodide”
(A) For elimination product C  H and C  X are eliminated in the same step
(B) The nucleophilicity order is Cl  I
(C) The percentage of substitution product is equal to percentage of elimination product
(D) Only the nucleofuge departs in the slow step
12.
Paragraph-IV
ALKYL HALIDE
13. Which of the following is compound P?

(A) (B)
(C) (D)
14. R and S are

(A) Position isomers (B) Enantiomes
(C) Geometrical isomers (D) Functional group isomers
15. Identify structure of compound T:

(A) (B)
(C) (D)
INTEGER
1.
On solvolysis, number of chlorine atoms replaced by –OH groups from the above substrate is
FIITJEE
Me Me
2. Et C Br 
H2 O
 Et C Br HBr
Me H
 80%racemisation 
The percentage of backside attach in Solvolysis reaction is given as 10x%. What is value of x.
FIITJEE
ANSWER
SINGLE CORRECT
1. D 9. D 16. A 24. C 32. B
2. A 10. C 17. B 25. D 33. C
3. A 11 B 18. C 26. D 34. B
4. D 19. 27. C 35. A
12. D
5. C 13. B
20. C 28. C
6. A 14. D 21. D 29
7. B 15 A 22. D 30. C
8. C 23. D 31. C
ONE OR MORE THAN ONE

1. A, B, C, D
2. BC
ASSERTION & REASONING
1. D
2. D
PARAGRAPH
1. C 6. C 11.
2. D 12.
7. B
3. C 13. A
8. A
4. B 14. C
9. A
15. B
5. B 10.
INTEGER
1. 3
2. 6

Fiitjee: Subject: Chemistry Alkyl Halide Aryle

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FIITJEE

SUBJECT: CHEMISTRY ALKYL HALIDE ARYLE

NAME…………………….. ENROLL NO……………. BATCH…………………

SECTION-I (ONLY ONE CORRECT)

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

Which substance will give maximum racemisation?

6. Pyrrol + Phenyl magnesium bromide  E + F

The structure of the products (E) to (H) respectively are

7. The major product obtained in the following reaction will be

14 The relative rates of chlorination at various positions in 1-Flurobutane are

(A) 3 > 1 > 2 > 4 (B) 2 > 3 > 1 > 4

16. Pyrrol + Phenyl magnesium bromide  E + F

The structure of the products (E) to (H) respectively are

17. The major product obtained in the following reaction will be

21. In the reaction

22. Some allylic carbocations are prepared as follows

23. 3,5-dimethylcyclopentene reacts with N-bromo succinimide (NBS) in CCl4 in presence of

25. Consider the following substarates:

The correct order of reactivity towards SN2 would be

27. Which of the following statements is false

32. Select the incorrect statement about Grignard reagent

33. Which cannot undergo E2 reaction

(A) Hoffmann elimination (B) Cope reaction

SECTION-II (ONE OR MORE THAN ONE)

2. During the chlorination of 3–chloronitrobenzene the possible product(s) is/are

4. Which of the following represents a resonance structure of benzyne?

Consider the following reactions:

The major product (IV) is

The major product (V) is

(A) Only H (or D ) is eliminated in the rate determining step

13. Which of the following is compound P?

14. R and S are

15. Identify structure of compound T:

ONE OR MORE THAN ONE

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