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Alkyl Halides and Aryl Halides - QB
Alkyl Halides and Aryl Halides - QB
A)H3C I B) I CH3
C2 H 5 C2 H 5
H3C
C) Mixture of (A) and (B) D) CH3
CH3 2 NH H2 /Pd
3. F NO2 X Y; Y is
DMF /
CH 3
A) H2N N B) H NH2
CH 3
NH2
H3 C H3C
C) N D) N NO 2
CH3 H3C
Ph
Me H alc.KOH
4. The organic compound (P) of the reaction P is
Br H
Ph
Ph Ph
Ph Me Ph Me Me H Me H
A) B) C) D)
H H H OH
H Ph Ph H
Ph Ph
Cl Cl
t - BuO
5. A ; A is
t - BuOH
t-BuO
O
A)
B)
O
Cl Ot-Bu
C) D)
O O
6. The ease with which an alcohol can be halogenated by treating it with HX in the presence of
anhydrous ZnCl2 is
FeCl3
A) + Cl2
low temperature
Cl
Cl Cl
uv light
B) + Cl2
high temperature
Cl Cl
Cl
CH3
CH 2 Cl
light, high temp.
C) + Cl2
no. catalyst
N N Cl Cl
CuCl, heat
D) + N2
C) H3C O C N D) H3C N C O
10. An alkyl halide of formula C6H13Cl on treatment with potassium t-butoxide gives two
isomeric alkenes C6H12 . Both alkenes on hydrogenation give 2, 3, dimethyl butane.
Isomeric alkenes are
H3C H3 C
A) CH3 CH3
H2C and H3C
CH3 CH3
H3C
H 3C
B) CH3
and
H 2C
CH3
CH3
H3C CH3
CH3 and
C) H3C
H3C CH3
CH3
H3C
D) CH3
and H2C
H2C
CH3
CH3
11. An Alkyl halide with molecular formula C6H13Br on treatment with alcoholic KOH gave two
isomeric alkenes A and B. Ozonolysis of the mixture gave the following compounds.
H3C C CH3 , H3C CHO , H3C CH2 CHO and (H3C)2HC CHO
O
The alkyl halide is
A) 2-Bromohexane B) 3-Bromo-2-Methylpentane
C) 2,2-dimethyl-1-Bromobutane D) 2-Bromo-2,3-dimethylbutane
F
(1)
(3)
O
O S
O O
(2) O
A) 3 > 1 > 4 > 2 B) 2 > 1 > 3 > 4 C) 1 > 2 > 3 > 4 D) 4 > 3 > 1 > 2
CH3
15. Br CH 2 (CH2)2 CH Br + H3C NH 2 product is
CH3 CH3
A) N B) N C) N CH3 D) N CH3
CH 3
H CH3 CH3 H
CMe3 CMe3
C) D)
Br Cl
OH
NaNH2 H
19. Intermediate ? Product
liq .NH3
Br
Choose the correct statement (s).
OH
A) is formed.
NH2
B) Intermediate formed is aromatic
OH
NH2
D) is also formed
OH OH
20. Amongst following the right statements are
A) In SN 2 reactions if reactant has R configurations the product has S configuration.
B) In SN 2 reactions the configuration of reactant gets inverted.
C) In SN 2 reactions if reactant is dextrorotatory the product is laevorotatory.
D) In SN 2 reactions if reactant has R configuration the product can have R or S
configuration.
21. Which of the following compound will be least reactive towards NaOH?
CH3
Cl
A) CH3Cl B) C) D) H3C
Cl
Br
HOH
22. In the given reactionH3C I X ; [X] will be
HO
A) H3C OH B) H3C
C) H3C D) H3C
HO
HOH
23. In the given reactionH5C6 CH CH CH2 Br X + Y ; [X] and [Y] are
OH
CH2
A) H5C6 OH B) H5 C6
CH2
C) D) H5C6
OH
24. Major product of the below reaction
O
18 dil.OH
HO C CH2 CH2 CH2 Br
O 18 O
C 18 C
A) O B) O
O O
C) HO C CH2 CH2 CH2 OH D) HO C CH2 CH CH2
25. Which of the following on treatment with NaNH2 in liquid NH3 gives m- anisidine?
A) o-Bromonaisole B) m-Bromoanisole
C) p-Bromoanisole D) Chlorobenzene
26. Which of the following reaction result in a product with more number of carbon atoms than
the starting compound?
A) Fitting reaction B) Gattermann reaction
C) Wurtz reaction D) Dow’s process
27. In the reaction CHCl3 4 OH H COO 3Cl 2H2O . The intermediate species formed
in above reaction.
A) CCl3 B) :CCl2 C) CH OH3 D) COCl2
Br Br Br CH3 3 CBr
30. When nitrobenzene is treated with Br2 in presence of FeBr3 the major product formed is
m-bromonitrobenzene. Statements which are related obtain the m-isomer are
A) The electron density on meta carbon is more than on ortho and para position
B) The intermediate carbonium ion formed after initial attack of Br at the meta position is
least destabilized.
C) Loss of aromaticity when Br attacks at the ortho and para position and not at meta
position.
D) Easier loss of H to regain aromaticity from the meta position than from otho and para
positions.
31. Benzyl chloride C6H5CH2Cl can be prepared from toluene by chlorination with
A) SO2Cl2 B) SOCl2 C) Cl2 D) NaOCl
LET US ADVANCE
A-1
SINGLE OPTION CORRECT TYPE
1. A SOCl2 B SO2 HCl
A Na C H2
B C (C2H5 )O NaCl
Then A is
A) C2H5Cl B) C2H5OH C) C2H6 D) C4H10O
2. Chlorination of Toluene with an excess of Cl2 in the presence of light and heat gives
product(X). The compound (X) is heated with Aqueous NaOH and finally acidified to give a
compound(Y). Y is
CH3 CH CH
3 3
OH COOH
A) B) C) D)
OH
OH
3. Bottles containing C6H5I and C6H5CH2I lost their original labels. They are labelled as A and
B for testing. A and B were separately taken in test tubes and boiled with NaOH solution.
The end solution in each tube was made acidic with dil. HNO3 and some AgNO3 solution
added. Solution B gives a yellow precipitate. Then which of the following statement is true for
experiment
A) Addition of AgNO3 was unnecessary B) A was C6H5I
C) A was C6H5CH2I D) B was C6H5I
50 C - 60 C reduction CH3COCl
4. C6H6 + HNO3 + H2SO4 A B C . Then C is
A) Aniline B) Nitro benzene C) Acetanilide D) Benzedine aniline
C NO 2 HOH
H3 CO CH CH P
CH3 CH3
The major product ‘P’ is
CH3
A) MeO CH CH C NO2
CH3 OH CH3
CH3 H CH3
B) MeO C C C NO 2
OH H CH3
CH3
C) MeO CH CH C NO2
CH3 CH3 OH
OH
I
Me C H KSH
6.
Et C D DMSO
H
SH H H SH
Me C H Me C H HS C Me H C Me
A) B) C) D)
Et C D Et C D Et C D Et C D
H I H H
i) B2H6 /OH
7. (A), Product (A) is
ii) SOCl2 / pyridine
Me
A) Me B) Me C) Me D) Me
Cl Cl OH OH
NaCN
A
8. H3C CH CH2 Cl , (A) and (B) would be
CH3 B
AgCN
CH3 CH3
CH3 CH3
CH3 CH3
C) H3C C CN and H3C CH CH2 NC
CH3
CH3
D) H3C CH CH2 CN and H3C C NC
CH3 CH3
9. Under specified conditions substance ‘X’ undergoes substitution and elimination reactivity to
give A D . A and B are stereoisomers. But not enantiomers. C and D are elimination
products. A is not an isomer of C. Which of the following could be the staring material ‘X’?
Br CH3
CH3
Br
A) B)
Me H H3C
H
Br
H 3C Br
CH3
C) D)
H
CH3
H3 C H
10. Which of the following will best convert nitrobenzene into 3-Fluorobromobenzene?
NO2 Br
F
A) F2 / AlCl3 , NaNO2 /HCl 0 C-5 º C ,CuBr
B) Br2 /FeBr3 , reduction, NaNO2 /HBF4 0ºC,
C) Reduction, NaNO2 /HBF4 0ºC, Br2 /FeBr3
D) Reduction, Br2 /FeBr3 ,NaNO2 /HBF4 0 ºC,
MULTIPLEOPTION CORRECT TYPE
11. Reaction between neo-pentyl bromide and ethanol gives 2-ethoxy-2methylbutane as the
major product because _________.
CH3
H3 C CH 2 Br
CH3
A) This involves a 1, 2-hydirde shift
B) This involves a 1, 2-alkyl shift
C) This occurs through a SN1 mechanism
D) This is also accompanied with the formation of alkenes as by product.
CH3
CH2OH HO
OH
OH
A) B) C) D)
15. Chloro benzene on heating with conc. KOH under pressure gives phenol. The correct
statement about the reaction is
A) It is addition elimination reaction
B) It is an electrophilic substitution reaction
C) The reaction involves benzyne intermediate
D) All are correct
OH
Br Br
COOH
B) Compounds E is
CH2
COOH
C) Compounds E is
O
OH
COOH
D) Compounds F is
CH2 Ph
OH
A) B) C) Cl CH2 NH2 D) H3 C CH Cl
Cl HC CH2
Cl
I H2 C CH CH 2 Cl
18. A B
acetone ZnCl2
Br
I
A) (A) can decolourise Br2 water
B) (B) decolourise Br2 water
C) (B) on hydrolysis produces optically active product
D) (A) is a diiodide
COMPREHENSION TYPE
Passage-1
An organic compound (A) has molecular formula C5H9Br . (A)decolourises brown colour of
bromine water but does not rotate plane polarized light. (A) on treatment with
HBr / PhCO2 O2 from C5H10Br2 which on further treatment with Na /R2O gives a cyclic
compound which on dibromination gives eight isomeric products.
CH2 Br
A) H3C B) H3C
Br
C) D) H3C CH2
CH2
Br
20. Compound (A) on treatment with HBr will produce.
A) An achiral dibromide B) A racemic mixture
C) A single pure enantiomer D) A meso dibromide
21. The true statement regarding the monochloro derivative product formed in the reaction
below is
H2Ni Cl2
(A) Monochlorination
UV
A) Three position isomers are formed B) Total five isomers are produced
C) Two pair of enantiomers are formed D) A pair of diastereomers are formed
Passage-2
In the study of chlorination of propane, four products (A), (B), (C) and (D) (structural
isomerism) of the formula C3H6Cl2 were isolated. Each was further chlorinated to provide
trichloroproducts C3H5Cl3 .
It was found that A provide one trichloro product, (B) gave two and (C) and (D) each gave
three. It is found that (D) is optically active.
C) CH3CH2CHCl2 D) CH3CHClCH2Cl
Cl
KOH aq
Cl CH2 CH3
B) Q) SN Ar
Cl
O2 N
KOH aq
C) Cl NO2 R) SN
O2 N
T) No reaction
Ag. powder
B) CHCl3 Q) Chloropicrin
KOH alc.
C) CHCl3 + CH3NH2 R) Hypnotic
HNO3 conc.
D) CHCl3 S) Acetylene
T) Chloretone
INTEGER TYPE
27. Number of possible products (including stereo isomers) for the following substrate.
Br
alc.KOH
29. The well insecticide gammexane is one of the stereoisomers of hexachlorocyclohexane. How
many moles of reagent. We need for conversion of benzene into hexachlorocyclohexane?
30. From the list of compounds given below ‘X’ is the number of compounds do not show SN 2
then the value ‘X’?
Cl Br Cl
CH 2 CH 2 CH 2 Br Cl
,
, , , ,
F
CH2 Br
Cl
, , ,
,
Cl
Cl
A-2
O CH3
2. is converted into by
Br
A) (i) CH3 — MgI, H3O (ii) H2SO4 , , (iii) HBr, R2O2
B) (i) CH3 — MgI, H3O (ii) H2SO4 , , (iii) HBr
H
N Br2
3. In the given reaction X ; X is
H Br H
N N N N
A) Br B) C) Br D)
Br
Br Br
4. Identify the set of reagents / reaction conditions 'X' and 'Y' in the following set of
X Y
transformation H3C CH2 CH2Br product H3C CH CH3
Br
A) X = dilute aqueous NaOH, 20 °C; Y = HBr/acetic acid, 20 °C
B) X = concentrated alcoholic NaOH, 80 °C; Y = HBr/acetic acid 20 °C
C) X = dilute aqueous NaOH, 20 °C; Y = Br2 /CHCl3 , 0 °C
D) X = concentrated alcoholic NaOH, 80 °C; Y = Br2 /CHCl3 , 0 °C
O
O
Based on the above reaction [C] should be
O
CH2
CH2 CH2 Cl
CH2 CH2 CH2 C Cl CH2 C
A) B)
O
CH2 CH2 OH
CH2 C
C) D)
O
O
CH3
6. Hofmann HBr
H3C CH CH CH3 (B) (C)
Elimination
Br HBr
R2O2
(D)
Correct order of rate of SN1 for (A), (C) and (D) will be
A) (A) > (C) > (D) B) (C) > (D) > (A) C) (A) = (C) > (D) D) (C) > (A) > (D)
i) NBS (A)/
7. (A) (B) , (B) will be
ii) alc KOH
A) B) C) D)
Br
CH3OH
8. In the given reaction C CH 2 [X] .[X] as the major products among the
CH3
following elimination product is
CH3
A) C CH 2 B) C CH 3
CH3
CH3
CH3
C) D) CH3
CH3
H 2C CH 2 CH3
C) H D)
H3C OH O
A) X Y Br
Br
B) X Y
C) X Y
Br
CH3
D) X Y Br
O
D) Chloral
15. Identify the compounds that will undergo neighboring group participation reaction.
A)H3C CH2 S CH2 CH2 Br B) H3C NH CH2 CH2 CH2 Br
C) H3C CH C O D) H3C O CH2 CH2 CH2 Br
Br O
16. Rate of SN 2 depends on
A) Conc. of Nucleophile B) Conc. of substrate
C) Nature of leaving group D) Nature of solvent
17. Which of the following reaction(s) is(are) feasible?
NaCN
A) CH3 3 CBr (H3C) 2C CH2 + HCN
NaHS
B)R CH2 Cl R CH2 SH + NaCl
Br
C)R CH2 SH2 R CH2 Br + H2S
i) p - TsCl
D)R CH2 OH R CH2 CN + OH
ii) NaCN
DMF
18. True statement among the following is/are
A) The weaker base after the group departs, the better the leaving group.
B) A reactive leaving group would raise the energy of the product, driving the equilibrium
towards the reactants.
C) Better leaving group only increases SN 2 rate, not SN1 .
D) Relative leaving group ability may vary with change of solvent.
COMPREHENSION TYPE
Passage-1
A leaving group in an alkylating agent can be displaced not only by a nucleophile added to
the reaction mixture but also by one in the alkylating agent itself. This holds for alkylating
agents that contain a nucleophilic electron pair at a suitable distance from the leaving group.
This neighboring group displaces the leaving group stereoselectively through backside attack
and this attack corresponds to the of an SN 2 reaction. The nucleophilic electron pairs of the
neighbouring group can be non-bonding, or they can be in a -bond. The higher rate of
reversal substitution reactions are explained using this neighboring group participation.
Et Et OH
A) N B) N
Et OH Et
Et Et OH
C) N D) N
Et OH Et
Passage-2
Br2
H3C C R HCBr3 + RCOO
OH
O
In the haloform reaction, methyl ketones (and the only methyl aldehyde, acetaldehyde) are
cleaved with halogen and a base. The halogen can be bromine, chlorine or iodine. What takes
place is actually a combination or two reactions. First under the basic conditions, the methyl
group is trihalogenated. Then the resulting trihalo ketone is attacked by hydroxide ion.
OH
Br3C C R + OH Br3C C R CBr3 + RCOOH
O O Shift Proton
RCOO + CHBr3
Iodine is most often used as the test reagent, since idoform is an easily indentiflable yellow
solid.
22. The idoform reaction is often used as a test for
A) Methanol B) Ethanol C) Propan-1-ol D) Butan-1-ol
23. For the test of methyl ketones which of the following reaction preferred?
A) Chloroform reaction B) Bromoform reaction
C) Idoform reaction D) Reduction
O
I2 /NaOH aq. NaOH aq. Proton
24. H3C C H P Q + R S + T ; R is
Transfer
from R to Q
A) Formic acid B) Acetic acid
C) Formate ion D) Acetate ion
MATRIX MATCHING TYPE
25. Match the Column-I with Column-II (Number of structural isomers produced in E2-
elimination) and select the correct answer.
Column-I Column-II
Br
A) P) 3
Br
B) Q) 0
Br
C) R) 1
D) S) 2
Br
26.
Column-I Column-II
A) Cl P) i Hg OAc 2 ; ii NaBH4
OH
C) R) EtBr
i BH3
D) S)
ii H2O2 /OH
OH
INTEGER TYPE
27. The number of compounds which give white precipitate with alcoholic AgNO3 is
Cl
Cl Cl CH3
Cl
Cl
Cl
Cl
H3 C Cl H3 C
I Br Cl
Br
, ,
,
Cl Br
Br Br Cl
,
, , Cl , ,
KEY
STRENGTHEN THE SKILLS
1. D 2. B 3. A 4. B 5. B 6. B 7. D
8. A 9. B 10. A 11. B 12. B 13. C 14. D
15. C 16. D 17. AC 18. AB 19. AB 20. AD 21. CD
22. AB 23. AB 24. AB 25. ABC 26. AC 27. AB 28. BCD
29. AB 30. AB 31. AC
LET US ADVANCE
A-1
1. B 2. D 3. B 4. C 5. B 6. D 7. A
8. D 9. C 10. B 11. BCD 12. BCD 13. ACD 14. AD
15. AC 16. ABD 17. AD 18. BC 19. C 20. B 21. C
22. B 23. C 24. D 25. A-R,B-T,C-QR,D-PRS
26. A-RT,B-S,C-P,D-Q 27. 3 28. 7 29. 3 30. 3
A-2
1. A 2. A 3. D 4. B 5. B 6. D 7. C
8. C 9. B 10. B 11. AC 12. BD 13. ACD 14. BCD
15. ABCD 16. ABCD 17. ABD 18. ABD 19. A 20. B 21. B
22. B 23. C 24. A 25. A-S,B-R,C-P,D-Q 26. A-Q,B-R,C-P,D-S
27. 5 28. 2 29. 2 30. 6