2B-Alcohols, Ethers & Phenols - FINAL - 06!03!14 (86-112)

JEE ADVANCED-VOL - VIII ALKYL HALIDES & ARYL HALIDES
EXERCISE
LEVEL - IV
OH
H+
1.

CH3
CH2 CH3
(A) (B) (C) (D)
OH H+
2.
?

CH2 CH3 CH2 CH2
(A) (B) (C) (D)
H 2O
3 . M ajor product is ?
Cl
H 3 CO NO 2
(A) (B) OH
OH
H 3 CO NO 2
H3CO NO2
OH
(C) (D) OH
H3CO NO2
H3CO NO2
86 Narayana Junior Colleges

ALKYL HALIDES & ARYL HALIDES JEE ADVANCED-VOL - VIII
Cl
a Cl CH 3 OH
4. b
c
O Cl
Which of the following statements is correct ?

(A) major product is formed at a . (B) major product is formed at b .
(C) major product is formed at c . (D)Reaction does not take place.
TsCl
HS OH A B
5. Pyridine
B is
SH
SH HO
S O
(A) (B) (C) (D)

OH
H2C
OH PCC /CH2Cl2
6.
H3C
H3C
(A) H3C (B)

H3C
O O
(C) H3C (D) H3C

CH3 CH3
O
PBr3 Mg / Ether H3O+
7. C H CH OH A B C D
6 5 2
(A) C6H5CH2OCH2CH3 (B)C6H5CH(OH)CH2CH2OH

(C) C6H5CH2CH2CH2OH (D)C6H5CH2CH2 OCH3
Narayana Junior Colleges 87
CH2
H+
8. OH ?
CH3 CH2 CH3 CH2

(A) O (B) O (C) O (D) O
H3C
OH SOCl2
9. H3C
?
CH3
H3C OH H3C Cl H3C H3C

Cl
(A) H3C (B) H3C (C) H3C (D )H3C
CH3 CH3 CH3 CH3
10 . A C6H12O compound does not react with Br2 in CCl4, produces a flammable gas on treatment
with LiAlH4, and reacts with H2CrO4 changing the color from orange to green. Which of the
following compounds best agrees with these facts?
(A)1-methylcyclopentanol (B) methoxycyclopentane
(C)2-cyclopropyl-2-propanol (D) 2-cyclobutylethanol
O O
CH3 x moles of HI CH3 y moles of HI
11.
Sum of x and y is
(A) 2 (B) 3 (C) 4 (D) 5
18
O H+/H2O
CH3
12.
H3C
Products formed are

18 18
18 H O H O
OH CH3 OH CH3
(A) & (B) &
H3C H3C
HO 18 HO
O O
(C) & (D) &

CH3
O O
AlCl3
CH 3
Product formed is?
13. 
CH(CH 3 ) 2
CH3 CH3 CH3

OH OH
O
(A)H3C (B)
O CH(CH3)2 CH(CH3)2
CH3 CH3
OH OH
(C) (D) H3C
CH(CH3)2 O CH3
Cl
OH
-
H 3C CH 3 OH /
+ ?
14.
NO 2
CH3 H3C O
O
(A) (B) NO 2
CH3 NO 2 CH3
O O
H3C
(C) (D)
H3C CH3 NO2 H2C CH3 NO2
15. Which of the statements is incorrect?

(A)2,4,6 trimethyl phenol is less acidic than 2,4,6trinitrophenol.
(B)2,6 dichlorophenol is stronger than 3,5 dichloro phenol
(C)para nitro phenol is more acidic than meta nitro phenol.
(D)para chloro phenol is less acidic then para flouro phenol.
HO
H+
16 . ?
OH
(A) (B) (C) (D)

O HO OH
17. Appropriate product among the following.
OH OH
D CDO D CHO
(A) (B)
D
OH O
ODC CHO D CHO
(C) (D)
CH3
OH
18. H+ (major)
?
CH3
CH3
CH3
(A) (B)
CH3 CH3
CH2 CH3
(C) (D)

19. A C7H14O optically active alcohol is oxidised by jones reagent to an optically inactive ketone
.The molecule is .
HO
OH
H3C OH O
(A) (B) (C) (D)

OH
HO HO
O H + / H 2O
20. ?
O
O O
HO OH
(a) ( b) (c) CH3 (d)
OH
HO
HO
OH
(i)CHCl3 + KOH
21. ?
(ii)CH2I2 + NaOH
OH
OH OH O OH
(A) (B) (C) (D)

HOOC OH OHC OH OHC O OHC OH
22. A chiral C5H10O ether reacts with hot HI to give a C5H10I2 product. Treatment of this with hot
KOH in ethanol produces 1,3-pentadiene. What is the structure of the original ether?
CH3 CH3
CH3 CH3
(A) (B) (C) (D)H3C
O O O O
23. A chiral C7H16O2 diol is oxidized by PCC in CH2Cl2 to an achiral C7H12O2 compound.
Which of the following would satisfy these facts?
H3C H3C H3C H3C
OH OH OH OH
H3C H3C
(A) H3C OH
(B) H3C OH
(C) H3C OH (D) H3C OH
H3C H3C H3C H3C

24. A chiral C5H10O alcohol is reduced by catalytic hydrogenation to an achiral C5H12O alcohol.The
original alcohol is oxidized by activated MnO2 to an achiral carbonyl compound (C5H8O)Which
of the following might be the chiral alcohol?
(A)1-penten-3-ol (B) 4-penten-2-ol
(C)3-methyl-2-buten-1-ol (D) 2-methyl-2-buten-1-ol
25. Which of the following ethers is unlikely to be cleaved by hot conc. HBr?
O O O O
CH3
(A) (B) (C) (D)
26. Phenol reacts with Phthalic anhydride in the presence conc. H 2 SO4 to give
(A) Methyl orange (B) Phenolphthaline (C) Aspirin (D) Methyl Blue
27.
- +
O Na
CO2 Ac2O
A B
 H3PO4
Identitify B in the sequence
(A) Methyl orange (B) Phenolphtheline (C) Aspirin (D) Methyl Blue
O
O HO
28.
OH x OH
In the above transaformation ‘X’ could be
(A) NaBH 4 C2 H 5OH H 3O  (B) N 2 H 4 OH  Glycol | 
(C) LiAlH 4 Et2O H 3O  (D) DIBAL  H THF H 3O 
HO OH O O
29.
H3C H3C H
The above transformation can be done by using

(A) Baeyer’s Reagent (B) Tollen’s reagent
(C) Pyridinium dichromate in CH 2Cl2 (D) Jone’s reagent
30. An unknown organic compound (A) having M.F. C3 H 8O3 reacts with an excess of acetyl chloride
gives an acetyl derivative with M.Wt. 218. Then howmay hydroxyl groups are in ‘A’.
(A) 2 (B) 3 (C) 4 (D) 5
MULTIPLE CORRECT ANSWER TYPE QUESTIONS
31. HBO and Oxymercuration -Demercuration , and acid catalysed hydration will not give the same
product in
CH2
CH3
(A) (B)
H3C CH3 CH2
CH3
(C) (D)
32. Which method is usefull synthesis of ether
(A)
-
(B)H C O + (CH3)2SO4
3 Na
-
O + H3C
Na
(C) H3C + O SO2C6H5CH3
(D)(CH3)3CBr + CH 3CH2ONa
33. Which of the following alcohols donot give white turbidity on treatment with HCl/ZnCl2
CH3
N
H3C H3C OH
(A) (B) OH (C) (D)
OH
OH CH3
34. Which of the following gives positive victormeyer test and yellow precipitate with NaOH / I2
OH NO 2
H3C H3C
(A) (B) (C) (D)H3C
H3C CH3 OH OH CH3
35. Which of the following is correctly matched
CH3
HI H3C O H+/H2O
(A)H3C O SN1 (B) CH3 SN1
CH3 CH3 CH3
H3C O HI
CH3 HI SN2
(C) (D) O SN1
CH3

36. In which of the following ring expansion / ring contraction takes place when protic acid is added
to the compound?
HO
OH
CH3
(A) (B)
CH3
OH
(C) (D) OH
H3C
37. Which of the following undergo reimer tiemann reaction?
OH CH3 OH NO2
O
(A) (B) (C) (D)
38. Which of the following statements is (are) correct?

(A) Nitration of phenol is faster than phenyl acetate.
(B) Reaction of phenoxide ion is faster than para cyano phenoxide With PhCH2Cl.
(C) Base cataltsed hydrolysis of p-nitrophenyl acetate is faster than phenyl acetate.
(D) Acid catalysed esterification of phenol is faster than p-nitro phenol.
39. Which of the follwoing compounds would give alcohol on reduction by LiAlH 4 / Et2O / H 3O 
O
O O-
(A) (B)
O
O
O O
O O
C) D)
CH
Cl HO
3
HO
40. Select the correct statemnts from the follwoing
(A) P-methoxy phenol is more reactive than P-nitro phenol towards Reimer-Tieman reacton.
(B) Phenol gives ortho isomer predominantly than para isomer in Reimer-Tieman reacton.
(C) The electrophile involved in R.T.R is Cl  .
(D) Para cresol is less reactive than phenol in R.T.R.
41. Which of the follwoing speces would you expect to obtain when P-creaol is subjected to Reimer-
Tieman reacton.
OH
OH O O
CHO
(A) (B) (C) (D)
CH 3 CHCl2 CH 3 COO H
CHO
COMPREHENSION TYPE QUESITONS

COMPREHENSION -1
1-chloromethyl -4 - methyl - 1,3 -cyclopentadiene is solvolysed in aqueous acetone
based on the above solve the following questions.
42. Which of the intermediates is not possible?
(A) (B) (C) (D)
43. Which of the following product is not formed ?

OH
(A) (B) OH
OH
(C) HO (D)
44. The number of enantiomeric pairs formed during the reaction is

(A)1 (B) 2 (C) 3 (D) 4
COMPRAHENSION - 2
The alkali metals (Li, Na, K etc.) and the alkaline earth metals (Mg and Ca, together with Zn) are good
reducing agents, the former being stronger than the latter. Sodium, for example, reduces elemental chlorine
to chloride anion (sodium is oxidized to its cation), as do the other metals under varying conditions. In a
similar fashion these same metals reduce the carbon-halogen bonds of alkyl halides. The halogen is converted
to halide anion, and the carbon bonds to the metal (the carbon has carbanionic character). Halide reactivity
increases in the order: Cl < Br < I .These reactions are obviously substitution reactions, but they cannot be
classified as nucleophilic substitutions, as were the earlier reactions of alkyl halides. Because the functional
carbon atom has been reduced, the polarity of the resulting functional group is inverted (an originally
electrophilic carbon becomes nucleophilic).Reactions of organolithium and Grignard reagents reflect the
nucleophilic (and basic) character of the functional carbon in these compounds.The nucleophilic carbon of
these reagents also bonds readily with electrophiles such as iodine and carbon dioxide. The polarity of the
carbon-oxygen double bonds of CO2 makes the carbon atom electrophilic, shown by the formula in the
shaded box, so the nucleophilic carbon of the Grignard reagent bonds to this site.
45. What is the product (B) of the following reaction sequence ?
O
Br
Mg
A B
Et2O
Hydrolysis of B gives
OH
OH
(A) (B)
OH
(C) (D )
OH
OH
46.
Product formed is
OH O
OH OH
(A) (B)
Et Et
OH O
OH OH
(C) (D)
Et Et

COMPRAHENSION -3
Ring-opening reactions of epoxides can proceed by either SN2 or SN1 mechanisms, depending on the
nature of the epoxide and on the reaction conditions. If the epoxide is asymmetric, the structure of the
product will vary according to which mechanism dominates. When an asymmetric epoxide undergoes
solvolysis in basic methanol, ring-opening occurs by an SN2 mechanism, and the less substituted carbon is
the site of nucleophilic attack. Conversely, when solvolysis occurs in acidic methanol, the reaction occurs
by a mechanism with substantial SN1 character, and the more substituted carbon is the site of attack. These
are both good examples of regioselective reactions. examine the basic, SN2 case first. The leaving
group is an alkoxide anion, because there is no acid available to protonate the oxygen prior to ring opening.
An alkoxide is a poor leaving group, and thus the ring is unlikely to open without a ‘push’ from the
nucleophile. Like in other SN2 reactions, nucleophilic attack takes place from the backside, resulting in
inversion at the electrophilic carbon. The best way to depict the acid-catalyzed epoxide ring-opening
reaction is as a hybrid, or cross, between an SN2 and SN1 mechanism. First, the oxygen is protonated,
creating a good leaving group. Then the carbon-oxygen bond begins to break and positive charge begins
to build up on the more substituted carbon .
answer the folllowing based on the above:
CH3CH2OH Product formed is?

47. O
NaOH
OH OH
(A) (B)
OCH2CH3 OCH2CH3
OH OH
(C) (D)
OCH2CH3 OH
- +
O CH O Na
48. Cl 3 The final product that is formed in the reaction is
HO OH
(A) H3CO (B) HO OCH3

O CH3
HO
CH3
(C) O O (D) Cl
O CH3
O 1 EQV PhS 
O
49. The product formed after nucleohillic attack and
OH
mild hydrolysis is
O O
O O
(A) O (B) O
OH OH
O O
O O
(C) O (D) O
OH OH
COMPRAHENSION- 4
Where E = electrophile, L.G. = Leaving Group

based on the above answer the following
50. Which of the following combinations give aryl alkyl ethers on heating
(A) O 2N Cl & +Na -O
(B) Cl & +Na - O
(C) Cl & +Na-O
Cl & +Na-O
(D)
O2N
51 . Which of the following does not give phenolic type compound on acidic hydrolysis .
O
O O
O
(A) (B) (C) (D)
52. Which of the following products cannot be formed without blocking reagent action on phenol ?
OH
OH
Br Br
COOH
(A) (B)
Br
OH
O
Br
(C) (D)

COMPRAHENSION- 5
Compound (A), C10H12O gives off hydrogen on treatment with sodium metal and decolourises Br2 in
CCl4 to give (B), C10H12OBr2. (A) on treatment with I2 in NaOH gives iodoform and an acid (C) after
acidification. Give the structures of (A) to (C) and also of all geometrical and optical isomers of (A).
Answer the following based on the above.
53. Compound A is
OH
(A) (B)
HO
HO
(C) (D )
O H
54. Compound B is
Br
Br
Br
Br
(A) (B)
HO
HO
Br
Br
(C) (D ) HO Br
HO
55. Which of the following statements regarding A are incorrect ?

(A) In the presence of acidic medium Aforms a 5 membred ring.
(B) A has 2 geometrical isomers.
(C) A has 4 pairs of diasteereomers.
(D) A has 2 chiral centres

MATRIX MATCHING TYPE QUESTIONS

56. column 1 column 2
( pair of alchols ) ( Tests which can distinguish them)
HO
OH
(A) Ph Ph
(P) Iodoform test
and
OH
(B) and OH (Q)Victor mayor test
OH
(C) (R)Lucas test.

CH3CH2OH and
OH
(D) OH (S) sodium dichromate in acidic medium Under

and
normal conditions.
57. COLUMN -1 COLUMN - II

O
OH-
(A) (P)Involves carbocation formation
O
O Ph
H+,H2O
(B) (Q) Acyl cleavage
O
Conc.HI
(C) (R) Racemic mixture
O
HI
H3CO CHD
(D) O NO2 (S) Product gives iodoform test

58. COLUMN I COLUMN II
H CH3
H

H  
O
(A) D (P) Isotopic effect
Cl P
O
Cl
CH3
Conc.H 2SO 4
D
(B) OH  (Q) Zaitsev’s product
OTs
R3N
H
(C) CH3 (R) Rearrangement
H
CH3
Conc.H2SO4
(D) Ph CH3 (S)Bimolecular elimination
OH

INTEGER TYPE QUESTIONS

OH
H+
59. The number of pi bonds in the final product is
60.The number of moles of Periodic acid used in oxidation of

H
H
HO O
HO
H H is
H OH
HO OH

61. During the reaction of Benzene diazonium chloride with para-cresol the substitution occurs at
___ position of p-cresol.
62. on heating forms _____ membred ring transition state.
OH
H+
63. The number of dehydration products are ___
64. The number of intermediates + transition states passible during the following reaction is ___
OH
H+
65. The number of moles of dichromate used in oxidation of RCH2OH to RCO2H is ______
66. The number of moles of Manganate ion used in oxidation of cyclopentene to cyclopent( 1 . 2 )diol
is__
67 . The number of moles of HIO3 formed during periodic oxidation of cyclohexa (1,2,3) triol ____
68. The number of compounds that undergo ring expansion on reaction with H2SO4 is
OH
OH OH OH
OH
HO OH
OH
OH
OH

STATEMENT TYPE QUESTIONS
This section contains 4 reasoning type questions. Each question has 4 choices (A), (B), (C) and (D), out
of which ONLY ONE is correct.
(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 NOT a correct
explanation for STATEMENT–1
(C) STATEMENT–1 is True, STATEMENT–2 is False
(D) STATEMENT–1 is False, STATEMENT–2 is True
69. STATEMENT–1 : > rate of dehydration.

OH OH
STATEMENT–2 :Rate of dehydration is directly proportional to stability of carbocation
NO 2
OH
O
Basic medium
70. STATEMENT–1 :
+
O 2N
Cl
STATEMENT–2 : reaction proceeds by electrophillic aromatic substitution.
H H
14 (1)TsCl CH3
H3 C
71. STATEMENT–1 : HO
OH (2)H2O 14
H3C CH3
STATEMENT–2 : Reaction proceeds via inversion of configuration in SN2

O O 18
18
+ H O
O O Ph
Ph H / H 2O
72. STATEMENT–1 : H3C H3C H + Ph
Ph Ph
Ph
O
18
O
Ph
STATEMENT–2 : Hydrolysis of H3C involves unimolecular mechanism.
Ph
Ph

HO O HO O
73. STATEMENT–1 : is more acidic then

HO O HO O
HO O
STATEMENT–2 : Conjugate base of is more stable

HO O
CH 3
O 2N
74. STATEMENT–1 : Cl undergoes inversion in DMSO with hydroxide ion
Br
STATEMENT–2 : The reaction proceeds by SN2 mechanism.
75. STATEMENT–1 :In protic solvents phenoxide ion is alkylated primarily at C-alkylation whereas in
polar aprotic solvents O-alkylation with alkyl halide .
STATEMENT–2 : C-alkylation products are more stable then O-alkylation products.
76. STATEMENT–1 :Optically active 2-iodo octane looses its optical activity with NaI in acetone
STATEMENT–2 : Repeated walden inversionon the reactant and its product gives racemic mixture
77. STATEMENT–1 :Phenol undergoes kolbe’s reaction while cyclohexanol does not.
STATEMENT–2 :Phenoxide ion is more basic then ethoxide
78. STATEMENT–1 :Para chloro phenol is more acidic then para flouro phenol.
STATEMENT–2 :negative inductive Effect if flourine is greater then in chlorine
LEVEL - IV - KEY
SINGLE ANSWER TYPE QUESTIONS
01.B 02.A 03.B 04.C 05.B 06.B 07.C 08.A
09. B 10. D 11. B 12.D 13.A 14.A 15.D 16.A
17.D 18.A 19.C 20.B 21.C 22.B 23.B 24.A
25.D 26. B 27. C 28.C 29. C 30. B
ONE OR MORE THAN ONE ANSWER QUESTIONS
31.A,B,D 32.A,B,C 33.A,C 34.A,C 35.A,B,C 36.A,B,C,D 37.A,B
38.A,B,C 39. A,B,C,D 40. A,B 41. B,C
COMPREHENSION QUESTIONS
42. d 43. d 44. b 45. a 46.c 47. a 48. c 49. a
50. a 51. a 52. c 53. a 54. a 55. d
MATRIX MATCHING QUESTIONS
56. A-P,S, B-P,R , C-Q,R, D-QRS 57. A-Q,S , B-P, R ,S, C-P,S , D-R,P
58. A-P, B-R, C- P,Q,S, D-R
INTEGER TYPE QUESTIONS
59.7 60.3 61.2 62.6 63.4 64.9 65.2 66.2
67.2 68.3
STATEMENT TYPE QUESTIONS
69.D 70.C 71.D 72.D 73.A 74.A 75.B 76.A
77.C 78.B

LEVEL IV HINTS
OH +
CH2 +
CH
01.
+ +
CH2 CH CH2 CH2
OH
02.
03. intermediate is more stable leading to B

H 3 CO NO 2
Cl Cl
Cl Cl
04.
O O
SH TsO
05. tosyl chloride makes hydroxide a poor leaving group into good leaving group and reaction
proceeds via SN2 mechanism
06.
07. Alkyl bromide reacts with Mg to form grignard reagent.R part of grignard reagent acts a as nucleophile
leading to epoxide ring opening.
+
CH CH3 CH3
08. OH O

O
Cl S
O
09.
10. OH
11. aryl ethers require only 1 mole while the other compound requires 2
H H
18 + 18
O O 18
12. O
13. fries rearrangement . The hydroxyl group directs the incomming electrophile at para position with respect
to it.
14. aryl halides undergo nucleophillic aromatic substitution in the presence of strong -R group at ortho , para
position .
15. para chloro phenol more acidic then para flouro phenol since para chloro phenoxide has larger number
of resonance stablised structures due to presence of d orbital..
HO
+
C +
16. C
HO O
17. Reimer tiemann mechanism .
CH3 CH3
+
C
+
CH2 CH3
18.
O O
19.
HO O
OH
20.
OH HO
21. reimer-tiemann reaction and nucleophillic substitution of phenoxide with alkyl halide.
I
CH3 CH3
H 2C
CH3
22. O
I
H3 C H3 C
OH O
H3 C H3 C
H3 C H3 C
OH O
23.
H3 C H3 C
(2S,4S)-3,3-dimethylpentane-2,4-diol
HO
24.
1-penten-3-ol
25. oxygen is in conjugation with 2 phenyl rings ,does not undergo cleavage
26. Formation of phenolphthalein

27. Kolbe’s reaction forward by acylation
28. Only LiAlH 4 redcues COOH group.
29. Conceptual
30. No. of OH groups = difference in molecular weight / 42
31. Cyclohexene only gives same product.
32. (CH3)3CBr + CH 3CH2ONa gives elemination.

33. Reaction with lucas reagent involves formation of stable carbocation.Soecies that cannot form stable
carboaction donot give white turbidity.
34. iso alcohols are oxidised to methyl ketones or acetaldehyde gives haloform reaction.Victormayer test
is given by alcohols.
35. Ethers in which both alkyl groups bonded are primary in acidic medium do not form
carbocations and hense donot undergoSN1 REACTIONS.
36. Ring expansion takes place if a carbocation is formed out side the ring.
37. reimer tiemann reactions occur via formation of phenoxide intermediate.If it isnt formed no reaction.
38. Acetate group on phenol decreases avaliability of electron density on benzene
Cyano group decreases nucleophilicity of phenoxide ion.
Base attack on carbonyl carbon in ester increases if electrophilicity of that carbon increeases.
During esterification alchol is nucleophile attacking.Electron withdrawing group on alchol decreases its
nucleophilicity ,rate of esterification decreases.
39. conceptual
40. Reimer-Tieman reaction
41. According to Reimer-Teiman reaction

42.
43. Cannot be formed hint :
44. OH OH and HO
HO
COMPRAHENSION-2
45. grignard reagent formed attacks cyclic ether by SN2 mechanism .Carbon nucleophile attacks at less stearically
hindred side as steraic hinderence increases grignard reaction does not occur .
O
46. grignard reagent is unstable in the presence of acidic hydrogen .
MgBr
formed does not react with grignard reagent.
COMPRAHENSION-3
47. read comprahension
48. epoxides undergo SN2 reaction .Alkoxide formed becomes a good incomming group and
c-cl bond becomes a good leaving group.
O
O
OH
49.
O

COMPRAHENSION -4
50. aryl halides with -R groups at ortho para positions undergo nucleophillic aromatic substitutions.The reaction
represents SN reaction.
51. ring expansions do not take place if existinfg ring is already stable.
O
O
O
O
O
O
HO 3 S
HO 3S
B r o m i n a t io n
s u l p h o n a t io n
52.
SO 3H
SO 3H O
O
OH
H O 3S Br
desulphonation Br
hydrolysis
S O 3H
COMPREHENSION -5
(For Q.NOs. 53-55)
12
hint : D.B.E. of (A) = 10 – +1=5
2
Since (A) decolouries bromine water and adds only a molecule of bromine, (A) should have a double
bond.
 D.B.E. of A = 5; it should also have a benzene ring.
(A) gives positive iodoform test and should have structure of the type
R — CHCH3 (R = alkyl/aryl group)
OH
CH = CHCHCH3 CHBrCHBrCH(OH)CH3
Br2
Hence (A) = OH CCl4
(B)
CH = CHCHCH3 CH = CHCOOH
I2
CHI3 +
OH NaOH Iodoform
(A) (C)

(A) has a chiral carbon and exists in two enantiomeric forms:
CH = CHC6H5 CH = CHC6H5
H OH HO H
CH3 CH3
(A) has two geometrical isomers:

C6H5 H
CH(OH)CH3 CH(OH)CH3
C=C C=C
H H C6H5 H
(cis) (trans)
56. Conceptual
57. Conceptual
58. Conceptual
OH
H+
59.
60. Only 1 , 2 cis diols participate in oxidation leading to ring cleavage

61. 2
62. 6
63.
OH2
64.

65. 3RCH2OH + 2Cr2O72- + 16H+ 3RCO2H + 4Cr3+ + 11H2O
OH
66. OH + 2MnO2 + 2OH-

+ 2MnO4- + 4H2O
67. Conceputal
68. after forming carbocation if carbocation is outside the ring then ring expansion takes place.
69. Stability of carbocation at bridge head is unstable.

70. Reaction proceeds via nucleophillic aromatic substitution or addition elemination mechanism.
H H
14 (1)TsCl 14
CH3
H3 C
71. HO
OH (2)H2O
H3C CH3
+ H O
H O 18
O Ph Ph
18
O + C
+
Ph H3C
72. H3C Ph
Ph
Ph
O-
-O -O O -O O-
O -O
73.
O
-O -O O O O O
O
74. Even though carbon bromine bond is weaker then carbon chlorine bond , bromine in conjugation does
not undergo SN reaction .
75. In protic solvents alkyl halide frms carbocation ,an electrophile,participates in electrophillic aromatic
substitution.
76. Repeated waldin inversionon the reactant and ist product gives racemic mixture.
77. Hint : Phenoxide ion is less basic then ethoxide.
78. parachloro phenoxide is resonance stablised by P  d conjugation.


2B-Alcohols, Ethers & Phenols - FINAL - 06!03!14 (86-112)

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JEE ADVANCED-VOL - VIII ALKYL HALIDES & ARYL HALIDES

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

CH2 CH3 CH2 CH2

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

86 Narayana Junior Colleges

Which of the following statements is correct ?

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

(A) H3C (B)

(C) H3C (D) H3C

(A) C6H5CH2OCH2CH3 (B)C6H5CH(OH)CH2CH2OH

CH3 CH2 CH3 CH2

H3C OH H3C Cl H3C H3C

Products formed are

88 Narayana Junior Colleges

CH3 CH3 CH3

(C) (D) H3C

15. Which of the statements is incorrect?

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

17. Appropriate product among the following.

90 Narayana Junior Colleges

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

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

Narayana Junior Colleges 91

In the above transaformation ‘X’ could be

(A) NaBH 4 C2 H 5OH H 3O  (B) N 2 H 4 OH  Glycol | 

(C) LiAlH 4 Et2O H 3O  (D) DIBAL  H THF H 3O 

The above transformation can be done by using

MULTIPLE CORRECT ANSWER TYPE QUESTIONS

32. Which method is usefull synthesis of ether

Narayana Junior Colleges 93

38. Which of the following statements is (are) correct?

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

COMPREHENSION TYPE QUESITONS

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

43. Which of the following product is not formed ?

44. The number of enantiomeric pairs formed during the reaction is

96 Narayana Junior Colleges

CH3CH2OH Product formed is?

(A) H3CO (B) HO OCH3

Where E = electrophile, L.G. = Leaving Group

(A) O 2N Cl & +Na -O

(B) Cl & +Na - O

(C) Cl & +Na-O

Narayana Junior Colleges 99

55. Which of the following statements regarding A are incorrect ?

100 Narayana Junior Colleges

MATRIX MATCHING TYPE QUESTIONS

(B) and OH (Q)Victor mayor test

(C) (R)Lucas test.

(D) OH (S) sodium dichromate in acidic medium Under

57. COLUMN -1 COLUMN - II

(D) O NO2 (S) Product gives iodoform test

Narayana Junior Colleges 101

INTEGER TYPE QUESTIONS

60.The number of moles of Periodic acid used in oxidation of

102 Narayana Junior Colleges

62. on heating forms _____ membred ring transition state.

Narayana Junior Colleges 103

STATEMENT TYPE QUESTIONS

69. STATEMENT–1 : > rate of dehydration.

STATEMENT–2 :Rate of dehydration is directly proportional to stability of carbocation

STATEMENT–2 : reaction proceeds by electrophillic aromatic substitution.

STATEMENT–2 : Reaction proceeds via inversion of configuration in SN2