14 Reaction Mechanism 2

Chemistry By
Vipul Sir
B.Tech. IIT
C
H
E
M REACTION
I MECHANISM
S 2
T
R
Y
PUSHKAR ENCLAVE, STADIUM ROAD, BAREILLY
PH. 9368239800
Chemistry...... Reaction Mechanism
REACTION MECHANISM
ADDITION REACTION
1.
(a) CH3OH / H+ (b) CH3CH2OH / H+ (c) H2O / H+ (d) HOCl / H+
2. CH3CH=CHCH3 ®
(a) CH3OH / H+ (b) H2O / H+ (c) CH3CH2OH / H+ (d) HOCl
3.
(a) CH3OH / H+ (b) H2O/H+ (c) CH3CH2OH/H+ (d) HOCl/H+

4. dil. H2SO4 /H2O®
Ph–CH2–CH=CH2 ¾¾¾¾¾¾¾¾
(a) (b) (c) (d) Ph–CH2–OH
5.
(a) (b) (c) (d)
6.
(a) (b) (c) (d)
7.
(a) (b) (c) (d)
8.
(a) (b)
(c) (a) and (b) (d)
MEDIIT CHEMISTRY: Pushkar Enclave, Stadium Road, Bareilly Ph. 9368239800 -2-
9.
(a) (b)
(c) (d)
10.
(a) (b) (c) (d)
11. HBr/R 2O2 ®

¾¾¾¾¾¾
(a) (b) (c) (d)
12.
(a) (b) (c) (d)
13.
(a) (b)
(c) (d)
14.
(a) (b)
(c) (d)
15. Arrange in decreasing order of reactivity with HCl
(a) I<III<II (b) III>II>I (c) III>I>II (d) none

16. F3C–CH=CH2+HCl®
(a) (b) F3C–CH2–CH3 (c) (d) F3CCH2CH2Cl
17. Give the major product obtained from the reaction of the following with HBr
(a) (b) (c) (d)
(i) BH3 -THF

18. ¾¾¾¾¾¾¾ ®
(ii) H2O2 /OH-
(a) (b) (c) (d)
(i) BH3 -THF

19. ¾¾¾¾¾¾¾ ®
(ii) H2O3 /OHQ
(a) (b)
(c) (d)
(i) BD3 -THF

20. ¾¾¾¾¾¾¾ ®
(ii) H2O2 /OH-
(a) (b) (c) (d)
(1) BH
21. ¾¾¾¾3¾ ®
(2) H2O2 ,OH-
(a) (b) (c) (d)
(i) Hg(OAc)2/H2O
22. ¾¾¾¾¾¾¾¾®
(ii) NaBH4
(a) (b)
(c) (d)
23.
(a) (b) (c) (d) all of these
(i) Hg(O2CCH3 )2H2O

24. ¾¾¾¾¾¾¾¾¾¾ ®
(ii) NaBH4 + NaOH
(a) (b)
(c) (d)
Hg(OAc)2 /H2O
25. ¾¾¾¾¾¾¾®
NaBD4
(a) (b) (c) (d)
26. Allyl alcohol + Br2 / CCl4 ®
(a) (b)
(c) (d)
27. Ph–CH=CH2 ¾¾¾¾¾¾ aq. NaOH(leq.)

BrCl/CCl4 ®(A) ¾¾¾¾¾¾¾® (B)
(a) A is (b) B is
(c) A is (d) B is
28. Reactivity order towards electrophilic addition of the following alkenes is
I. CH2 = CH2 II. CH2 = CH – Cl III. CH3 = CH – CH2 IV.

(a) IV < III < I > II (b) IV > III > I > II (c) IV > I > III > II (d) IV > I > II > III
29. Rat eof hydration of the following alkenes is
I. CH3–O–CH=CH2 II. F–CH=CH2 III. CH3–CH=CH2 IV.

(a) I > II > III > IV (b) I < II < III < IV (c) I > IV > III > II (d) I > IV > II > III
30. Rate of addition of Cl2 / H2O of the following alkenes is
I. CH2 = CH2 II. CH2 = CH–CHO III. CH3–CH2–CH=CH2 IV.

(a) IV>III>I>II (b) IV>III>II>I (c) I>II>III>IV (d) I>II>IV>III
31. Reaction of HBr with propene in the presence of peroxide gives
(a) isopropyl bromide (b) allyl bromide (c) n-propyl bromide (d) 3-bromopropane
32. In the presence of platnium catalyst, hydrocarbon (A) adds hydrogen to form n-hexane. When hydrogen
bromide is added to (A) instead of hydrogen, only a single bromo compound is formed. Which of the following
is (A)?
(a) H2C=CH–CH2–CH2–CH2–CH3 (b) CH3–CH=CH–CH2–CH2–CH3
(c) CH3–CH2–CH=CH–CH2–CH3 (d) CH3–CH2–CH2–CH=CH–CH3
33. Alkene RCH=CH2 reacts readily with B2H6 and the product of oxidation with alkaline H2O2 produces
(a) (b) R–CH2–CHO (c) RCH2CH2OH (d)
34. The intermediate during the addition of HCl to propene in the presence of peroxide is
+ +
&
(a) CH 3CHCH (b) CH C HCH &
(c) CH 3CH 2CH (d) CH CH C H
2 Cl 3 3 2 3 2 2
35. The reaction of CH3CH=CH OH with HBr gives
(a) CH3CHBrCH2 OH (b) CH3CH2CHBr OH
(c) CH3CHBrCH2 Br (d) CH3CH2CHBr Br
36. HBr reacts with H2C=CH–OCH3 under anhydrous conditions at room temperature to give
(a) CH3CHO and CH3Br (b) BrCH2–CH2–OCH3
(c) BrCH2–CH2–OCH3 (d) H3C–CHBr–OCH3
37. CH3–CH=CH2+Br2 ¾¾¾¾¾ in NaCl® Products . The product, not expected in this reaction is
(a) Cl (b) (c) (d) all of these

38. Consider the following compounds
(1) Ph2C=CH2 (2) (CH3)2C=CH2 (3) Ph3C=CHCF3
Correct order of rate of electrophilic addition reaction is
(a) 1>2>3 (b) 3>2>1 (c) 1>3>2 (d) 3>1>2
H( + ) ®
¾¾¾
39. [A] Major, [A] will be
EtSH
(a) (b) (c) (d)
40. [A] may be
(a) (b)
(c) (d)
H( + ) ®[A]
¾¾¾
41. D2O , [A] will be
(a) (b) (c) (d)
42. A & B respectively are
(a) (b)
(c) (d)
43. [X] will be
(a) (b)
(c) (d)
44. Which of the following compound is most reactive towards electrophilic addition reaction?
(a) CH 2=CH2 (b) (F3C)2C=CH2
(c) NH–CH=CH–CHO (d)
EAS
1. (B) is
(a) (b) (c) (d)
2.
(a) (b)
(c) (d)
3. _
(a) (b) (c) (d)
4. Most reactive compound towards electrophilic substitution is
(a) (b) (c) (d) none
5. Arrange in order of decreasing reactivity towards electrophilic reagent in;

chlorobenzene (I), benzene (II), toluene (III), phenol (IV) would be
(a) IV>III>II>I (b) IV>I>II>III (c) II>I>IV>III (d) I>II>IV>III
6. In Friedel-Crafts reaction, the electrophilic reagent is
(a) AlCl3 (b) RCO+ (c) R C+
OCl (d) none
7. Which of the following compounds reacts slower than benzene in electrophilic bromination
(a) C6H5CH3 (b) C6H5OH (c) C6H5NO2 (d) C6H5NH2
8. In the following compounds, anisole (I), benzene (II) and nitrobenzene (III) the ease of reaction with electrophiles
is
(a) I>II>III (b) II>III>I (c) II>I>III (d) III>II>I
9. In the reaction p-chlorotoluene with K NH 2 in liquid NH3, the major product is
(a) o-toluidine (b) m-toluidine (c) p-toluidine (d) p-chloroaniline
10. I. II. III. IV.
(a) III>I>II>IV (b) IV>I>II>III (c) I>II>III>IV (d) II>I>III>IV

11. Identify the correct order of reactivity in electrophilic substitution reactions of the following compounds
I. II. III. IV.
(a) I>II>III>IV (b) IV>III>II>I (c) II>I>III>IV (d) II>III>I>IV

12. The major product obtained on the monobromination (with Br2/FeBr3) of the following compound 'A' is
(a) (b) (c) (d)
13. The strongest ortho-para and strongest meta-directing groups respectively are
(a) –NO2 and –NH2 (b) –CONH2 and –NH2 (c) –NH2 and –CONH2 (d) –NH2 and –NO2
14. Which of the following structures corresponds to the product expected, when excess of C6H6 reacts with
CH2Cl2 in presence of anhydrous AlCl3
(a) (b)
(c) (d)
15. Which of the following does not undergo Friedel-Crafts reaction

(a) Aniline (b) Phenol (c) Nitrobenzene (d) All
16. Which of the following groups deactivates the benzene ring towards electrophilic substitution
(a) –NHR (b) –OH (c) –COOR (d) –OR
17. Benzene reacts with CCl4 in presenceof anhydrous AlCl3 to give
(a) tetraphenyl methane (b) chlorobenzene (c) tetrachlorobenzene (d) triphenyl methyl chloride
18. Which xylene is most readily nitrated
(a) Ortho-xylene (b) Para-xylene (c) Meta-xylene (d) all at the same rate
HNO3 ®
¾¾¾¾
19. H2SO4 Product; Product of this reaction will be
(a) (b)
(c) (d)
20. In which of the following cases, the nitration will take place at meta-position
(I) (II) (III) (IV)
(a) II and IV (b) I, II and III (c) II and III (d) I only
21. 'X' is
(a) ortho-chlorobenzotrichloride (b) para-chlorobenzotrichloride

(c) meta-chlorobenzotrichloride (d) none
22. Which of the following is most reactive towards electrophilic substitution reaction
(a) (b) (c) (d)
23. When is treated with nitrating mixture (HNO3 + H2SO4), we get
(a) (b)
(c) (d)
SUBSTITUTION
1. Arrange the following nucleophiles in the order of their nucleophilic strength

(a) OH–>CH3COO–>CH3O–>C6H5O– (b) CH3COO–<C6H5O–<CH3O–<OH–
(c) C6H5O–<CH3COO–<CH3O–<OH– (d) CH3COO–<C6H5O–<OH–<CH3O–
2. Which of the following is least reactive in a nucleophilic substitution reaction
(a) (CH3)3C–Cl (b) CH2=CHCl (c) CH3CH2Cl (d) CH2=CHCH2Cl
3. The decreasing order of nucleophilicity among the nucleophiles is
(I) CH3 – – O– (II) CH3O– (III) CN– (IV)
(a) I, II, III, IV (b) IV, III, II, I (c) II, III, I, IV (d) III, II, I, IV
4. Among the following, the strongest nucleophile is
(a) C2H5SH (b) CH3COO– (c) CH3NH2 (d) NCCH–2
5. CH 3Br + Nu– ® CH3Nu + Br– . The decreasing order of the rate of the rate of the above reaction with
nucleophiles (Nu–) A to D is [Nu– = (A) PhO–, (B) AcO, (C) HO–, (D) CH3O–]
(a) D>C>A>B (b) D>C>B>A (c) A>B>C>D (d) B>D>C>A
6. The correct increasing order of the reactivity of halides for SN1 reaction is
(a) CH3CH2–X<(CH3)2CH–X<H2C=CHCH2–X<PhCH2–X
(b) (CH3)2CH–X<CH3CH2–<H2C=CHCH2<X<PhCH2X
(c) PhCH–X<(CH3)2CH–X<CH3CH2–X<H2C=CH–CH2X
(d) H2C=CHCH2–X<PhCH2–X(CH3)2CH–X<CH3CH2–X
7. The SN1 reactivity of the following halides will be in the order
(i) (CH3)3C–Br (ii) (C6H5)2CHBr (iii) (C6H5)2C(CH3)Br (iv) (CH3)2CHBr
(v) C2H5Br
(a) (iv)>(iv)>(i)>(ii)>(iii) (b) (ii)>(i)>(iii)>(v)>(iv) (c) (i)>(iii)>(v)>(ii)>(iv) (d) (iii)>(ii)>(i)>(iv)>(v)
8. In which alkyl halide, SN2 mechanism is favoured maximum
(a) CH3Cl (b) CH3CH2Cl (c) (CH3)2CHCl (d) (CH3)3C–Cl
9. Which one of the following is least reactive in a nucleophilic substitution reaction
(a) CH3CH2Cl (b) H2C=CHCH2Cl (c) (CH3)2CHCl (d) H2C=CHCl
10. Tertiary butyl chloride preferably undergo hydrolysis by
(a) SN1 mechanism (b) SN2 mechanism (c) and of (a) and (b) (d) none
11. In a S 2 substitution reaction of the type R – Br + Cl– ¾¾¾¾
N
DMF® R – Cl + Br–. Which one of the following
has the highest relative rate
(a) (CH3)3C–CH2Br (b) CH3CH2Br (c) CH3CH2CH2Br (d) (CH3)2CH–CH2Br
12. In the following carbocation, H/CH3 that is most likely to migrate to the positive charged carbon is
(a) CH3 at C-4 (b) H at C-4 (c) CH3 at C-2 (d) H at C-2
13. Which alkyl halide will react fastest with aqueous ethanol
(a) (CH3)3C–Br (b) (CH3)3C–Cl (c) (CH3)2CH–Br (d) CH3–CH2–CH2–Br
14. –
When the concentration of alkyl halide is tripled and the concentration of OH ion is reduced to half, the rat eof
SN2 reaction increases by
(a) 3 times (b) 2 times (c) 1.5 times (d) 6 times
15. In the given reaction, CH3CH2–X+CH3SNa®. The fastest reaction occurs when 'X' is
(a) –OH (b) –F (c) –OCOCF3 (d) OCOCH3
16. The compound which undergoes fastest reaction with aq. KOH solution is
(a) C6H5 – –OCH3 (b) C6H5– –CH3 (c) C6H5–CH2–CH2–Cl (d) C6H5– –CH2–CH3
17. The rate of SN1 reaction is fastest with
(a) (b)
(c) (d)
18. Which of the following alkyl halide is hydrolysed by SN1 mechamism

(a) (CH3)2CHX (b) CH3CH2X (c) CH3CH2CH2X (d) (CH3)3CX
19. Isopropyl chloride undergoes hydrolysis by
(a) SN1 mechanism (b) SN2 mechanism
(c) SN1 and SN2 mechanism (d) Neither SN1 nor SN2 mechanism
20. The order of reactivities of the following alkyl halides for a SN2 reaction is
(a) RF>RCl>RBr>RI (b) RF>RBr>RCl>RI (c) RCl>RBr>RF>RI (d) RI>RBr>RCl>RF
21. Consider the following two anionic molecules. Which of the following statements is TRUE ?
(a) I is more basic and more nucleophilic than II.

(b) I is less basic and less nucleophilic than II.
(c) I is more basic but less nucleophilic than II.
(d) I is less basic but more nucleophilic than II.
22. Consider ammonia (I) and water (II). Which of the following statements is TRUE ?
H3N : H2O :
I II
(a) I is more basic and more nucleophilic than II. (b) I is less basic and less nucleophilic than II.
(c) I is more basic but less nucleophilic than II. (d) I is less basic but more nucleophilic than II.
Period, Nucleophilicity & Basicity runs parallel. repulsion
23. Which halide ion is the best nucleophile in dimethyl sulfoxide solution ?
(a) Fluoride (b) Chloride (c) Bromide (d) lodide
24. Which is the best leaving group in a substitution reaction of an alkyl halide ?
(a) CF (b) Br– (c) I– (d) F–
25. Which statement is TRUE with respect to an SN2 reaction ?
(a) A good leaving group is a strong base. (b) A good leaving group is a weak base.
(c) A leaving group must be negatively charged. (d) A leaving group must be a halide.
26. The reaction of 3-chloro-2,2-dimethylbutane and sodium iodide yields
(a) 3-iodo-2,2-dimethylbutane (b) 2-iodo-3,3-dimethylbutane
(c) 3-iodo-2,3-dimethylbutane (d) 2-iodo-2,3-dimethylbutane
27. Rank the following in order of decreasing reactivity with methanol
(a) III>II>IV>I (b) IV>I>II>III (c) I>IV>II>III (d) I>IV>III>II

28. Which compound RX reacts most rapidly in an SN2 reaction
(a) 2-Bromohexane (b) 1-Bromo-3-methylhexane
(c) 2-Bromo-2-methylhexane (d) 3-Bromohexane
29. Which of the following can not be made in good yield from CH3CH2Cl using an SN2 reaction
(a) CH3CH2OCH2CH3 (b) CH3CH2OC(CH3)3 (c) CH3CH2OH (d) CH3CH2SH
30. What is the MOST reactive alkyl halide for the following reaction RX + H2O ® R–OH + X–
(a) (b) (c) (d)
31. Which of the following reaction is not possible

(a) R–OH+NaBr® R–Br+NaOH (b) R–OH+HBr®R–Br+H2O
(c) both reaction are possible (d) both reactions are not possible
32. Which of the following compounds will show NGP
(a) (b) (c) (d)
33. , Major product (A) is
(a) (b) (c) (d)
34. SOCl2 ®(A) . Product (A) in

¾¾¾¾
(a) (b) (c) (d)
35. Under identical conditions, solvolysis of which of the following substrates would lead to maximum recemization
(a) (b) (c) (d)
36. Which one of the following compounds will be most reactive for SN1 & SN2 reactions
(a) (b) (c) (d)
37. For the given reactiion :
Which substrate will give maximum racemisation?
(a) (b)
(c) (d)
38. Among the bromides I-III given below, the order of reactivity is SN1 reaction is
(I) (II) (III)
(a) III>I>II (b) III>II>I (c) II>III>I (d) II>I>III
39. (a) (b) (c) CH3–CH2–CH2Br
Reactivity towards SN1

(a) a>b>c (b) b>a>c (c) b>c>a (d) c>b>a
40. Which of the following compound give same SN1 and SN2 product?
(a) (b) (c) (d)
41. Which of the folloiwng compound will not undergo nucleophilic substitution reaction
(a) (b) (c) (d)
42. Most reactive towards SN2
(a) (b) (c) (d)
43. (a) R–I (b) R–Br (c) R–Cl (d) R–F

rate of SN2 is
(a) a>b>c>d (b) b>a>c>d (c) a=b=c=d (d) d>c>b>a
44. (a) R–I (b) R–Br (c) R–Cl (d) R–F
rate of SN1
45. ; Type of reactionis
(a) SN1 (b) SN2 (c) E2 (d) E1

KSH
46. R-2-chloro butane ¾¾¾®
acetone
(a) SN1 (b) SN2 (c) E2 (d) E1
EtOQ ®
47. R-2-chloro butane ¾¾¾¾
EtOH,D
(a) SN1 (b) SN2 (c) E2 (d) E1
48.
(a) SN1 (b) SN2 (c) E2 (d) E1
49.
(a) SN1 (b) SN2 (c) E2 (d) E1

(a) Me–O–CH2–Cl (b) Me–NH–CH2–Cl (c) Me– –CH2–Cl (d) Me–CH2–CH2–Cl

(a) Me–O–CH2–CH3 (b) Me–CH2–O– –Me (c) Me–CH2–O– –Me(d)
52. ; Product 'P' is
(a) Inverted product (b) Racemic (c) Retention product (d) Meso
53. Strongest nucleophile in polar-protic solvent
(a) CH 3OQ (b) CH3SH (c) CH 3 - SQ (d) CH3OH
54. Correct order of leaving group
(a) (b) IQ < N º N
(c) (d) all
55. Which Statement is correct about aliphatic nucleophilic substitution reactions?

(a) In SN2 racemisation takes place.
(b) In SNI complete racemisation occurs
(c) In SNI partial racemisation occurs and isomer with inverted configuration forms more.
(d) In SNI partial racemisation occurs and isomer having configuration similar to that of substrate forms more.
56. In which case racemisation takes place.
(a) (b)
(c) (d) All of these

57. Correct order of rate of SN2 is
(I) (II) (III) (IV)
(a) II>III>IV>I (b) III>II>IV>I (c) II>IV>III>I (d) I>III>II>IV

58. (–)
CD2=CH–CH2Br is subjected to nucleophilic substitution reaction by EtO in EtOH. Which of the following
statement will be most appropriate?
(a) both SN1 and SN2 give two products
(b) both SN1 and SN2 give only one product
(c) SN1 gives two products buth SN2 gives on product
(d) SN1 gives one product but SN2 gives two products
59. Suggest the suitable solvent for the reaction given below :
(a) H2O (b) C2H5OH (c) HCONMe2 (d) C6H6
60. In which case chances of SN2 are maximum
(a) Br + C2H5O(–) (in H2O) ® (b) Br + C2H5O(–) (in C2H6) ®
(c) Br + C2H5O(–) in DMF ® (d) Br + C2HO(–) in DMSO ®
61. (I) (II) (III) (IV)
Ease of SN1 reaction among these compounds will be in the order as

(a) I>III>II>IV (b) IV>III>II>I (c) III>II>I>IV (d) III>IV>II>I
62. Which one of the following will be hydrolysed with maximum rate
(a) C6H5Cl (b) (c) (C6H5)3CCl (d) C6H5CH2Cl
(-)
63. OH
¾¾¾ ® A , A is
in DMSO
(a) (b) (c) (d) All
64. Which path is better for the preparation of ROH
(a) Path I (b) Path II (c) both (d) None

65. Arrange the following groups in order of decreasing leaving group abaility for SN reaction
(I) CH3SO3– (II) CF3SO3– (III) tert BuO– (IV) I–
(a) I>II>III>IV (b) IV>I>II>II (c) III>II>I>IV (d) II>I>IV>III
( -) (-) (-)
66. Arrange the nucleophiles S H,Se H, &S H in order of their nucleophilicity in di mehyl formamide (DMF)
medium
( -) (-) (-) ( -) (-) (-) ( -) (-) (-) (-) (-) (-)
(a) O H > S H > Se H (b) Se H > O H > S H (c) Se H > S H > O H (d) S H > O H > Se H
67. Which is correct about the nucleophilicity of halide ion?
(a) In DMSO order of nucleophilicity is F(–)>Cl(–)>Br(–)>I(–) while in water is I(–)>Br(–)>Cl(–)>F(–)
(b) In DMSO order of nucleophilicity is I(–)>Br(–)>Cl(–)>F(–) while in water is F(–)>Cl(–)>Br(–)>I(–)
(c) Order of nucleophilicity is same as F(–)>Cl(–)>Br(–)>I(–) in both water & DMSO
(d) Order of nucleophilicity is same as I(–)>B(–)>Cl(–)>F(–) in both water & DMSO
68. Out of RI, RBr, RF and RCl the compound which undergoes SN rapidly is
(a) RI (b) RCl (c) RBr (d) RF
ELIMINATION REACTION
1.
Value of x is
(a) 1 (b) 2 (c) 3 (d) 4
2.
3. Major product (X) is
(a) (b) (c) (d)
4. The major products obtained when this substrate is subjected to E2 reaction will be
(a) (b) (c) both (a) and (b) (d) none
5. Major product of the reaction, is Alc.KOH ®

¾¾¾¾¾
(a) Butene-1 (b) Trans-2-butene (c) cis-2-butene (d) Butyne-1

6. In order to accomplish the following conversion, what reagent and conditions would be required?
(a) Cold sodium hydroxide (b) Hot conc. sodium hydroxide

(c) Potssium t-butoxide and heat (d) Hot water
Alc.KOH EtONa
7. CH3–CH2– – CH3 ¾¾¾¾¾® Major
X : CH3–CH2– –CH3 ¾¾¾¾® Major
Y
D
Product (X) & (Y) respectively is

(a) 1-butene, trans-2-butene (b) 1-butene, cis-2-butene
(c) cis-2-butene, 1-butene (d) trans-2-butene, 1-butene
8. (a) (b) (c) CH3–CH2–CH2Br
Reactivity towards E2
9. (a) (b) (c) CH3–CH2–CH2Br
Reactivity towards E1
10. (a) R–I (b) R–Br (c) R–Cl (d) R–F
rate of E2
11. (a) R–I (b) R–Br (c) R–Cl (d) R–F
rate of E1
12.
(a) SN1 (b) SN2 (c) E2 (d) E1
13.
(a) SN1 (b) SN2 (c) E2 (d) E1
14.
(a) SN1 (b) SN2 (c) E2 (d) E1

EtOQ ®
15. R-2-chloro butane ¾¾¾¾
EtOH,D
(a) SN1 (b) SN2 (c) E2 (d) E1
16.
(a) SN1 (b) SN2 (c) E2 (d) E1
17.
(a) SN1 (b) SN2 (c) E2 (d) E1

18. Ph–CH2– NaNH2 (A) . Total number of elimination product are (includes stereoisomer)
–CH2–CH3 ¾¾¾¾®
(a) 2 (b) 4 (c) 6 (d) 8
19. ¾¾¾¾¾ CH3I Ph - C º C - CH

xNaNH2 ®(A) ¾¾¾® .
3
Sum of (x+y=?)
(a) 2 (b) 4 (c) 5 (d) 6
20. . Major product of this reaction is
(a) (b) (c) (d)
21. [HEM = Hoffmann exaustive methylation] Product (B) is
(a) (b) (c) (d)
22. ; , (A) & (B) are
(a) (b)
(c) (d)
23. ; Product (A) is
(a) (b) (c) (d)
24. . Product (B) is
(a) (b) (c) (d)
25. . Type of mechanismof above reaction is
(a) A=SN1 B = SN2 (b) A=SN2 B = SN1 (c) A=SN1 B = E1 (d) A = E1 B = SN1
26.
(a) E1 (b) E2 (c) both E1 and E2 (d) E1CB

27. Which of the following compound will not undergo E2 reaction
(a) (b) (c) (d)
(+) ( -)
28. D ® Products, Which product will not form in this reaction?
(CH3)4 N O H ¾¾
(a) CH3OH (b) Me3N
(c) H2O (d) No product will form in this reaction
29. Product; This reaction follows :
(a) E1 pathway (b) E2 pathway (c) E1CB pathway (d) Unpredictable

30. Consider the following reactions.
2–Fluoro butane + CH3O( –) ® Products...................(A)
2–Chloro butane + CH3O(–) ® Products...................(B)
tert–butyl chloride + CH3OH ® Products...................(C)
tert–butyl chloride + CH3OH ® Products...................(D)
Out of the following statements
(a) In reaction (C), (B) & (A) elimination is prominent
(b) In reaction (D) substitution occurs via SN2 pathway
(c) The reaction (A) follows E1CB pathway
(d) In reaction (C) almost 100% elimination takes place when reaction mixture is subjected to heat.
Correct statement are
(a) 1, 2, 3 (b) 2, 3 (c) 1, 2, 3, 4 (d) 1, 3, 4
31. Number of possible products obtained by the acid catalysed dehydration of 3-methyl-pentan-2-ol is (do not
consider stereoisomers)
(a) 1 (b) 2 (c) 3 (d) 4
32. [X] Major, [X] will be
33. Dehydration of alcohol at higher temperature gives rise to alkene. The alcohol which undergoes acid catalysed
dehydration rapidly is
(a) (b) (c) (d) Ph–CH2OH
34. Which alkyl halide would you expect to be least reactive in an E1 reaction?
(a) (b)
(c) (d) Ph–CH2–CH2Br
35.
Here P is
(a) pent-2-ene (b) Pent-1-ene (c) Iso pentene (d) Iso butene
ANSWER KEY
ADDITION REACTION
1. A 2. C 3. D 4. A 5. A 6. B 7. A 8. D 9. A 10. B
11. A 12. C 13. A 14. B 15. B 16. D 17. B 18. C 19. C 20. A
21. B 22. B 23. A 24. A 25. B 26. A 27. B 28. B 29. C 30. A
31. C 32. C 33. C 34. B 35. B 36. D 37. A 38. C 39. C 40. B
41. C 42. D 43. B 44. A
EAS
1. A 2. A 3. A 4. A 5. A 6. B 7. C 8. A 9. B 10. A
11. C 12. B 13. D 14. D 15. D 16. C 17. A 18. C 19. C 20. B
21. C 22. D 23. B
SUBSTITUTION
1. D 2. B 3. D 4. A 5. A 6. A 7. D 8. A 9. D 10. A
11. B 12. D 13. A 14. C 15. C 16. A 17. A 18. D 19. C 20. D
21. C 22. A 23. A 24. C 25. B 26. A 27. C 28. B 29. B 30. C
31. A 32. A 33. B 34. A 35. C 36. A 37. C 38. A 39. A 40. C
41. D 42. D 43. A 44. A 45. B 46. B 47. C 48. A 49. C 50. B
51. D 52. C 53. C 54. D 55. C 56. B 57. B 58. D 59. C 60. D
61. A 62. C 63. C 64. B 65. A 66. A 67. A 68. A
ELIMINATION REACTION
1. C 2. A 3. A 4. B 5. B 6. C 7. D 8. A 9. A 10. A
11. A 12. C 13. D 14. C 15. C 16. C 17. C 18. B 19. C 20. C
21. A 22. B 23. B 24. B 25. C 26. B 27. A 28. C 29. A 30. D
31. C 32. A 33. C 34. C 35. C

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14 Reaction Mechanism 2

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Chemistry By

(a) CH3OH / H+ (b) H2O / H+ (c) CH3CH2OH / H+ (d) HOCl

(a) CH3OH / H+ (b) H2O/H+ (c) CH3CH2OH/H+ (d) HOCl/H+

(a) (b) (c) (d) Ph–CH2–OH

(a) (b) (c) (d)

(a) (b) (c) (d)

(a) (b) (c) (d)

(c) (a) and (b) (d)

(a) (b) (c) (d)

11. HBr/R 2O2 ®

(a) (b) (c) (d)

(a) (b) (c) (d)

(a) I<III<II (b) III>II>I (c) III>I>II (d) none

(a) (b) F3C–CH2–CH3 (c) (d) F3CCH2CH2Cl

(a) (b) (c) (d)

(i) BH3 -THF

(a) (b) (c) (d)

(i) BH3 -THF

(i) BD3 -THF

(a) (b) (c) (d)

(a) (b) (c) (d)

(a) (b) (c) (d) all of these

(i) Hg(O2CCH3 )2H2O

(a) (b) (c) (d)

27. Ph–CH=CH2 ¾¾¾¾¾¾ aq. NaOH(leq.)

28. Reactivity order towards electrophilic addition of the following alkenes is

I. CH2 = CH2 II. CH2 = CH – Cl III. CH3 = CH – CH2 IV.

I. CH3–O–CH=CH2 II. F–CH=CH2 III. CH3–CH=CH2 IV.

I. CH2 = CH2 II. CH2 = CH–CHO III. CH3–CH2–CH=CH2 IV.

35. The reaction of CH3CH=CH OH with HBr gives

(a) CH3CHBrCH2 OH (b) CH3CH2CHBr OH

(c) CH3CHBrCH2 Br (d) CH3CH2CHBr Br

(a) Cl (b) (c) (d) all of these

(a) (b) (c) (d)

40. [A] may be

(a) (b) (c) (d)

42. A & B respectively are

43. [X] will be

(c) NH–CH=CH–CHO (d)

(a) (b) (c) (d)

(a) (b) (c) (d)

4. Most reactive compound towards electrophilic substitution is

(a) (b) (c) (d) none

5. Arrange in order of decreasing reactivity towards electrophilic reagent in;

10. I. II. III. IV.

(a) III>I>II>IV (b) IV>I>II>III (c) I>II>III>IV (d) II>I>III>IV

I. II. III. IV.

(a) I>II>III>IV (b) IV>III>II>I (c) II>I>III>IV (d) II>III>I>IV

(a) (b) (c) (d)

15. Which of the following does not undergo Friedel-Crafts reaction

(I) (II) (III) (IV)

(a) ortho-chlorobenzotrichloride (b) para-chlorobenzotrichloride

(a) (b) (c) (d)

23. When is treated with nitrating mixture (HNO3 + H2SO4), we get

1. Arrange the following nucleophiles in the order of their nucleophilic strength

(I) CH3 – – O– (II) CH3O– (III) CN– (IV)

17. The rate of SN1 reaction is fastest with

18. Which of the following alkyl halide is hydrolysed by SN1 mechamism

(a) I is more basic and more nucleophilic than II.

(a) III>II>IV>I (b) IV>I>II>III (c) I>IV>II>III (d) I>IV>III>II

(a) (b) (c) (d)

31. Which of the following reaction is not possible

(a) (b) (c) (d)

33. , Major product (A) is