Practice Test – 02 Sarthak WBJEE Bangla 04/02/2024
CHEMISTRY
Section A 6. Identify the set of reagents/reaction conditions X
and Y in the following set of transformations-
1. The total number of alkyl bromides (including X Y
stereoisomers) formed in the reaction CH3CH2CH2Br → Product → CH3—CH—CH3
Me3C — CH = CH2 + HBr → will be |
(1) 1 (2) 2 Br
(3) 3 (4) no bromide forms (1) X = dilute aqueous NaOH, 20°C,
Y = HBr/acetic acid, 20°C
2. The major product of the following reaction is (2) X = concentrated alcoholic NaOH, 80°C,
F3C — CH = CH2 + HBr → Y = HBr/acetic acid, 20°C
(1) F3C — CH2 — CH2Br (3) X = dilute aqueous NaOH, 20°C,
Y = Br₂/CHCl3, 0°C
(2) F3C — CH(Br) — CH3
(4) X = concentrated aqueous NaOH, 80°C,
(3) F2C — CH(F) — CH3 Y = Br2 /CHCl3, 0°C
|
Br 7. The synthesis of alkyl fluorides is best
(4) F2CH — CH — CH3F accomplished by
|
Br (1) Finkelstein reaction
(2) Swarts reaction
3. The exact order of acidity of the compounds
(3) free radical fluorination
p-nitrophenol, acetic acid, acetylene and ethanol is
(1) p-nitrophenol < acetic acid < acetylene < (4) Sandmeyer's reaction
ethanol
(2) acetic acid <p-nitrophenol < acetylene < 8. Which reducing agent is used for the following
ethanol conversion ?
(3) acetylene <p-nitrophenol < ethanol < acetic RCOOH → RCH2OH
acid
(1) LiAIH4
(4) acetylene < ethanol <p-nitrophenol < acetic
acid. (2) NaBH4
(3) K2Cr2O7
4. The major product of the following reaction is (4) KMnO4
CH3 CH2CH – CH2 (i) KOH alc.
(ii) NaNH 2
Br Br in liq. NH 3 9. Cumene on reaction with oxygen followed by
(1) CH3CH2 CH — CH2 hydrolysis gives
| |
NH2 NH2 (1) CH3OH and C6H5COCH3
(2) CH3CH = CHCH2NH2 (2) C6H5OH and (CH3)2O
(3) CH3CH = C = CH2
(3) C6H5OCH3 and CH3OH
(4) CH3 CH2C CH
(4) C6H5OH and CH3COCH3
alc. KOH Hbr Nal
5. CH3 – CH – CH3 X Y Z
Peroxide Acetone
10. Methoxybenzene on treatment with HI produce
Br
In the given reaction what will be the final product ? (1) iodobenzene and methanol
(1) CH3CH2CH2I (2) phenol and methyl iodide
(2) CH3CHICH2I
(3) iodobenzene and methyl iodide
(3) CH3CH2CH2CH2CH3
(4) phenol and methanol
(4) CH3 CH2 CHI3
11. The correct order of reactivity of following 14. The correct order of pKa values for the following
haloarenes towards nucleophilic substitution with compounds is
aqueous NaOH is OH OH OH OH
Cl
(A)
Cl
(B)
NO 2 O
N NO 2o
Cl
(A) (B) (C)
(
(D)
(C)
(1) B > D > A > C (2) B > A > D > C
OMe
NO 2 O
(3) C > A > D > B (4) A > B > C > D
Cl
NH 2 h
(D)
O 2N
o
NO 2 O
15. NaNO 2 + HCl KI
X Y
Choose the correct answer from the options given 280 K
below :
(1) C > A > D > B (2) A > B > D > C X and Y in the reaction are
(3) D > B > A > C (4) D > C > B > A
12. The major product in the following reaction
(i) Hg(OAc) 2 , H2 O
(ii) NaBH 4
(1)
(1)
(2)
(2)
(3) (3 )
3
OH
OH
(4)
(4)
13. The compound which reacts fastest with Lucas
reagent at room temperature is
(1) butan-2-o1
(2) butan -1-o1
(3) 2-methyl propan-1-o1
(4) 2-methyl propan-2-o1
Section B K 2Cr2 O7 I2/NaOH
18. C4 H10 O C4 H8 O CHI3
5. H 2SO 4 warm
16. Identify X in the following sequence of reactions : N
CH3–CH–CH–CH2–CH2–CH3 Here, N is
| |
Br Br
(1) OH
(1) CH3 – CH – CH–CH2CH2CH3
| | OH
Br NH2
CH3 H (2)
(2) C C
H CH2 CH2 CH 3 (3) O
CH3 CH2 CH2 CH3 (4)
(3) C C OH
H H
(4) CH3 – CH – CH – CH2CH2CH3
19. The intermediate X, in the reaction
| | OH
OH
NH2 NH2 (i) NaOH
+ CHO is
(i) H
CHCl3 + [Link] + [X]
17. Identify the correct order of reactivity for the
following pairs towards the respective mechanism
Br OH
(A) Br
SN2 CCl3
c
Br (1)
Br
(B) Sn 1
OH
Cl Cl CHCl2 c
(2)
(C) Electrophilic substitution
– +
O Na
NO 2 o
CHC l2 c
(3)
Br
Br
– +
(D) Nucleophilic substitution O Na
CCl3 c
NO 2 o
(4)
Choose the correct answer from the options given
below :
(1) (A), (C) and (D) only
(2) (A), (B), (C) and (D) only
(3) (A), (B) and (D) only
(4) (B), (C) and (D) only
20. Find out the major product from the following
reaction.
H 2SO 4 (Concentrated)
OH
(1) (2)
(3) (4)
ANSWER KEY
Section A 11. (3)
1. (3) 12. (1)
2. (1) 13. (4)
3. (4) 14. (1)
4. (4) 15. (1)
5. (1) Section B
6. (2) 16. (2)
7. (2) 17. (2)
8. (1) 18. (2)
9. (4) 19. (3)
10. (2) 20. (2)
HINTS AND SOLUTION
Section A 6. (2)
1. (3) CH3CH2CH2 Br ⎯⎯⎯⎯⎯⎯
Alcoholic NaOH
→ CH3 − CH = CH2
80 C
CH 3
| ⎯⎯⎯
HBr
→ CH3 − CH − CH3
CH 3 − C − CH = CH 2 + H − Br → |
| Br
CH 3 7. (2)
CH 3 CH 3 Refer to Video Solution
| |
*
8. (1)
CH 3 − C − CH − CH 2 + CH 3 − C − C H − CH 2
| | | | | | Refer to Video Solution
Br CH 3 H CH 3 Br H
(Major product) (R+S)Minor 9. (4)
2. (1)
The major product of the given reaction is
F3C − CH2CH2Br .
Complete reaction is as follows : Cumene Cumene
F3C − CH = CH2 + HBr → F3C − CH2CH2 Br (Isopropyl hydroperoxide
benzene)
The presence of strong electron withdrawing group
leads to a formation of a less stable carbocation on
10. (2)
the middle carbon atom. The major product is
formed with respect to the stable carbocation on
terminal carbon atom attached to double bond.
3. (4)
11. (3)
Acidity : HC CH C2 H5OH The correct reactivity of haloarenes towards
nucleophilic substitutions with aq. NaOH is
pK a value : 25 16 7.1 4.75
1
Acidity ∝
pKa value
Generally, aryl halides are less reactive towards
nucleophilic substitutions with aq. NaOH due to
4. (4) presence of electron releasing group i.e., (−OCH3 )
The reaction proceeds as : which decreases its reactivity towards nucleophilic
Alc. KOH substitution. Whereas, the presence of an electron
CH 3CH 2 − CH − CH 2 → CH 3 − CH 2 − C = CH 2 withdrawing group i.e., (−NO2 ) at ortho and para
| | | position increases its reactivity towards
Br Br Br nucleophilic substitution. As the number of
NaNH2/liquid NH3 electron withdrawing groups increases, reactivity
CH 3 − CH 2 − C CH ⎯⎯
H+
CH 3CH 2 C CNa + increases.
12. (1)
5. (1)
CH3 − CH − CH3 ⎯⎯⎯⎯[Link]
→ CH 3 − CH = CH 2
| (X)
Br Oxymercuration - Demercuration reaction follow
⎯⎯⎯⎯HBr
Peroxide
→ CH3CH 2 CH 2 Br ⎯⎯⎯⎯
NaI
Acetone
→ CH 3CH 2CH 2 I Markownikoff's addition..
(Y) (Z)
13. (4) Section B
16. (2)
2-methyl propan-2-ol is a tertiary alcohol, will
react fastest with Lucas reagent CH 3 − CH − CH − CH 2 − CH 2 − CH 3
| |
Br Br
NaNH2, E2 path (NaNH₂
will perform double
dehydrohalogenation)
CH3 − C C − CH2 − CH2 − CH3
Na/liq. NH3 (Birch
14. (1) reduction; anti-addition of
H₂)
(A)
17. (2)
(A) SN2 reaction decreases with increase in steric
crowding.
(B) (B) SN1 reaction increases with stability of
carbocation.
(C) EAS reaction decreases with decrease in
electron density.
(D) Presence of electron withdrawing group at
ortho and para-position w.r.t. halogen in
haloarene increases nucleophilic aryl
substitution.
(C)
18. (2)
I 2 / NaOH
As, C 4 H 8O → CHI3
warm
So, C 4 H 8O should have − C − CH 3 group
(D) ||
O
19. (3)
Phenol in presence of sodium hydroxide reacts with
chloroform to form salicylaldehyde. The reaction is
K a value increases by electrons withdrawing group known as Reimer-Tiemann reaction.
i.e., NO2 . Hence, the order of K a value will be
20. (2)
C A D B. The major product from the following reaction is
1 given
Also, we know that, pK a
Ka
So the order of, pK a value is B D A C .
Thermodynamically
15. (1)
controlled product
Refer to Video Solution
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