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Alcohol Sheet
Alcohol Sheet
Exercise - 01
1. Which of the following reaction is called as ‘Bouveault–Blanc reduction’
(1) Reduction of acyl halide with H2/Pd-BaSO4 (2) Reduction of ester with Na/C2H5OH
(3) Reduction of anhydride with LiAlH4 (4) Reduction of carbonyl compounds with Na-Hg/HCl
2. Glycol on treatment with PI3 mainly gives–
(1) Ethylene (2) Ethylene iodide (3) Ethyl iodide (4) Ethane
3 Consider the reaction of HI with the following:
II
, ,
will be in order:
(1) I < II < III (2) I < III < II (3) II < I < III (4) III < II < I
6. The reaction of CH3OC2H5 with HI gives
(1) CH3I (2) C2H5OH (3) CH3I + C2H5OH (4) C2H5I + CH3OH
7. The number of methoxy groups in a compound can be determined by treating it with
(1) HI and AgNO3 (2) Sodium carbonate (3) Sodium hydroxide (4) Acetic acid
8. Most acidic alcohol out of following compounds is
(1) (CH3)3C–OH (2) CH3CH2OH (3) CH3OH (4) PhOH
9. Action of HNO2 on CH3NH2 gives following as major product
(1) CH3OH (2) CH3–O–CH3 (3) CH3–O–N=O (4) CH3–NO2
10. A compound ‘X’ with molecular formula C3H8O can be oxidised to a compound ‘Y’ with the molecular formula C 3H6O2, ‘X’
is most likely to be
(1) Primary alcohol (2) Secondary alcohol (3) Aldehyde (4) Ketone
11. Ether on carbonylation gives
(1) Alkanoic acid (2) Alkanone (3) Alkyl alkanoate (4) Alkanal
12. Phenol with Hinsberg’s reagent gives
(1) Sulphone (2) Sulphanilic acid (3) Sulphonic ester (4) Sulphonal
NaBH H / Pt
15. B
4 CH = CH – CHO 2
A, A and B are:
16.
will be in order
(1) IV > III > II > I (2) I > II > III > IV
(3) IV > II > III > I (4) II > IV > I > III
18. H ? Product is:
19. RMgX
? Product Obtained is:
H 2O
R R' R R
| | | |
(1) R 'C CH 2 OH (2) RCH 2 C OH (3) R ' CH C OH (4) R ' ' CH 2 C OH
2
| | | |
R'' R'' R'' R'
I / NaOH
20.
2
H A, A is
CH OH
21. [A]
CH OH
3
3
[B] A & B are:
H 2SO 4
CH3O
Cl NaBH4
25. (A) Product(s) is/are –
LiAlH4
(B)
(1) [A] is an Alcohol ; [B] is an Aldehyde (2) [A] is an Aldehyde; [B] is an Alcohol
(3) [A] and [B] both are Alcohols (4) [A] and [B] both are Aldehydes
O
HBr
28. Ph CH CH 2 OH Product. The product in the reaction is –
|
Ph
Br
/
(1) Ph CH CH 2 Br (2) Ph C CH 2 (3) Ph C CH 3 (4) Ph C CH 2 Ph
| | | |
Ph Ph Ph Br
Å Å
(3) CH 3 - CHCH 3 CH 3 - CH - CH 3 (4) None of these
OH
HNO2
31. major product, is –
CH2NH2
OH OH
(1) (2) (3) O (4) OH
CH2OH CH3
Passage (Q.32-Q.34)
Compound [A] (C8H8O) is obtained from styrene on treatment with CF3CO3H. [A] can also be obtained from C8H8ClO on
treatment with concentrated NaOH. [A] on treatment with HBr produces an optically active compound [B]. Styrene on
treatment with HBr, H2O2 and then treatment with Mg/ether produces [C]. Compound [C] on treatment with RCOR'
produces an alkene [D] and RCH(OH)R'. Sytrene is PhCH = CH 2.
32. Structure of compounds [A] is –
(1) Ph – CH – CH2 (2) Ph - CH - CH 2 OH (3) PhCH2CH2MgBr (4) PhCH = CH2
|
O Br
33. Structure of compounds [B] is –
(1) Ph – CH – CH2 (2) Ph - CH - CH 2 OH (3) PhCH2CH2MgBr (4) PhCH = CH2
|
O Br
34. Structure of compounds [C] is –
(1) Ph – CH – CH2 (2) Ph - CH - CH 2 OH (3) PhCH2CH2MgBr (4) PhCH = CH2
|
O Br
35. What is a likely product of the reaction shown?
(1) a > c > b (2) a > b > c (3) b > a > c (4) b > c > a
37. Major-product A is
41. Hydroboration of 1 - methylcyclopentene using B2D6 , followed by treatement with alkaline hydrogen peroxide, gives -
CH3
| H HBr
KMnO 4
42. CH3 CH ( A )
(B) (C)
| ROOR
CH3
H CH3 CH3
| | |
(1) CH3 C Br (2) CH3 C Br (3) CH3 CH2 (4) CH3 CH
| | | |
CH3 CH3 CH2 Br CH2 Br
43.
45. A is:
(1) (2)
(3) (4)
1.Hg( OAc ) ,H O
47. 2 2
Product; Product is -
2.NaBH 4
(3) (4)
49. Which of the following is the best set of reagents to perform the about conversion?
51. An organic compound A (Molecular formula C6H12O) does not change the colour of acidic dichromate solution. Compound
A on treatment with H2SO4 produces alkene, which on oxidative ozonolysis gives a molecule (C6H10O3) which gives positive
iodoform test. Find out structure of 'A'.
(1) Identical to A (2) Chain isomer of A (3) A positional isomer of 'A' (4) Reduced product of A
53.
(1) 1 > 2 > 3 > 4 (2) 1 > 3 > 2 > 4 (3) 4 > 3 > 2 > 1 (4) 4 > 3 > 1 > 2
55. Which of the following reactions proceeds with retention of configuration–
(1) (2)
(3) (4)
(1) (2)
(3) (4)
57. An organic compound having molecular formula C3H6O does not react with 2, –4dinitrophenyl hydrazine and does not react
with Na metal. The compound is expected to be–
(1) CH3CH2CHO (2) CH3COCH3 (3) CH2=CH–CH2–OH (4) CH2=CH–O–CH3
60. Which of the following ethers is the most unreactive to cleavage with conc. HBr ?
62.
64. Product–
65. (major)–
66.
68.
71. In which of the following group, each member gives positive iodoform test–
(1) methanol, ethanol, propanone (2) ethanol, isopropanal, methanal
(3) ethanol, ethanal, isopropyl alcohol (4) propanal, propanol–2, propanone
72.
Identify the position where the above acetylation reaction take place–
(1) a (2) b (3) c (4) d
73. Identify the reagents (1–4), required for the transformations shown and arrange them in correct order–
74.
When Grignard reagent reacts with (B) product (D) will obtained–
Reactant (A) of the above reaction is–
P.C.C.
(P) HO OH (i) CH MgBr
3
(Q) (R)
(S)
Lucas reagent
79. (2mole) (1 mole) (ii) H
CH2OH
PCC
80.
(X) Major
CH3 OH
OH
O O OH
O OH
Passage- Acid catalysed conversion of 1,2–diol or vicinal diol, into carbonyl compound known as pinacol–pinacolone rearrangement.
Generally more electron donating group migrate during mechanism, migration of —H is faster because of its smaller size.
82.
ANSWER-KEY
Qus. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. 2 1 3 4 1 3 1 3 2 1 3 3 4 1 2 3 3 4 2 1
Qus. 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40
Ans. 2 1 1 1 3 2 2 3 2 3 3 1 2 3 4 2 2 2 3 4
Qus. 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
Ans. 1 4 2 3 3 2 4 312 1 3 4 3 1 3 1 3 4 4 2 2
Qus. 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80
Ans. 2 1 3 1 2 2 2 2 2 4 3 2 4 1 4 4 3 1 1 3
Qus. 81 82 83(a) 83(b) 83(c) 83(d)
Ans. 3 3 135 5 4 2
O O
|| ||
(1) Me C Cl (2) Me C NH 2 (3) Me CH CH 2 (4) Me C OC Me
|| || \ /
O
O O
dil. H SO H
2. In the reaction sequence, CaC2 H
2O
A
2
4 B
2
C, true about the product C is
2 Ni
Hg
(1) give yellow ppt. with NaOI (2) its final oxidation product is carbonyl compound
(3) its final oxidation product is CO2 and H2O (4) its final oxidation product is CH3COOH
O O OH OH O O
|| || | | || ||
(1) CH3 CH2 CCH2 CCH3 (2) CH3 CH CHCH2 CH3 (3) (4) CH3 CCH2 CHCH2 CCH3
|
OH
4. HBO, oxymercuration-demercuration and acid catalysed hydration will not give same product in
BH ·THF H O , OH
(1) 3 2
2
NaOH
Hg ( OAc ) NaBH
(2) 4 NaOH
2
H 2O
(3) O OI
CHI3
(4)
7. Anhydride of alcohol is -
(1) Ether (2) Aldehyde (3) Alkyl hydrogen sulphur (4) Alkene
(1) H O CH3
CH3 CH3
NaOH
(2) C—C CH3OH
H O CH3
O
NaBH4 H+
(3) This is only affected in reduction to 2° alcohol
(4) R–C–OH + H–O–R
CH3OH
NaOMe / MeOH
(i) MeOH
,H
P (ii) Q
(1) Alcohol (2) Ether (3) Alkyl chloride (4) Alkyl nitrite
(3) l (4) OH
17. Alkan-1,2-diols are oxidised into two fragments when treated with –
(1) periodic acid (2) lead tetraacetate (3) anhydrous ZnCl2 (4) conc. H2SO4
18. Which of the following reagents or process are suitable to distinguish MeOH and EtOH ?
OH
COOH & H
1)H ,H O Aq.KOH
(3) R CH CH 2
2
(4) R CH 2 CH 2 x
Alcohol Reagent
CH 3 CH CH 2 CH 2OH
|
(1) CH 3 B2H6 , H2O2 / NaOH
OH
|
(3) CH C CH CH B2H6 , H2O2 / NaOH
3 2 3
|
CH 3
OH
|
CH 3 C CH 2 CH 3
(4) | dil. H2SO4
CH 3
22. Match the following:
Reaction Mechanism
H3O
(A) (p) change in number of carbon in cycle
heat
(C) H
(r) Oxidative bond cleavage
heat
H O
(D)
3
(s) Ketone as product
heat
CH2OH CH3 OH
H2SO4
(A) (p)
CH2OH
P, I2
(B) (q)
O CH2–I
(C) 3 H O (r)
CH3MgI
CH3
CH3 |
| H 3O
(A) (p) CH 3 C OH is one of the product of the reaction
CH3 C O CH CH 3 |
| | CH3
CH3 CH 3
CH3 OH
H3O
(B) O C CH3 (q) is one of the product of the reaction
CH3
CH3
H3O
(C) O CH (r) CH 3 CH OH is one of the product of the reaction
CH3 |
CH3
ANSWER SHEET
Qus. 1 2 3 4 5 6 7 8 9 10
Ans. 1 14 2 124 12 13 1 124 1234 123
Qus. 11 12 13 14 15 16 17 18 19 20
Ans. 12 1 34 1234 12 14 12 12 134 1234
Qus. 21 22(A) 22(B) 22(C) 22(D) 23(A) 23(B) 23(C) 23(D) 24(A)
Ans. 124 qs rs p s qrt r s p q
Qus. 24(B) 24(C) 25(A) 25(B) 25(C)
Ans. r p pr pq qr
(1) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(2) Oxidation with acidic dichromate followed by reaction with Fehling solution
(3) Oxidation by heating with copper followed by reaction with Fehling solution
2. Select the correct order of boling point of following compound [JEE 2002]
1 2 3
(1) 1 > 2 > 3 (2) 3 > 1 > 2 (3) 1 > 3 > 2 (4) 3 > 2 >1
C H O Na ( excess )
3. OH + C2H5I
2 5 [JEE 2003]
C 2 H5OH ( anhydrous)
O O
Heat I
2 [F] [G]
[E]
Ph * OH NaOH
(* implies 13C labelled carbon)
O O O O
(1) E = F= G = CHI3 (2) E = F= G = CHI3
* * – + – +
Ph Ph ONa Ph * Ph ONa
CH3 CH3
O O O O
* *
(3) E = F= G = CHI3 (4) E = F= G = CH 3I
– + – +
Ph * Ph ONa Ph * Ph ONa
CH3 CH3
Column I Column II
8. Match the chemical conversions in List I with the appropriate reagents in List II and select the correct answer using the code
below the lists. [JEE-Advance -2013]
List-I List-II
Codes:
P Q R S
(1) 2 3 1 4
(2) 3 2 1 4
(3) 2 3 4 1
(4) 3 2 4 1
with NaBH4 ( NOTE : stereoisomers are also reacted separately). The total number of ketones that give a racemic product
(s) is/are-
[JEE-Advance -2014]
10. The acidic hydrolysis of ether (X) shown below is fastest when
[JEE-Advance -2014]
ANSWER SHEET
Qus. 1 2 3 4 5 6 7(A) 7(A) 7(C) 7(D) 8
Ans. 3 2 4 4 3 3 rs t pq r 1
Qus. 9 10
Ans. 5 3
(3) alcohols having resonace structures (4) intermolecular hydrogen bonding in ethers.
2. During dehydration of alcohols to alkenes by heating with conc. H2SO4, The initiation step is [AIEEE-2003]
3. Acetyl bromide reacts with excess of CH3MgI followed by treatment with a saturated solution of NH 4Cl gives -
[AIEEE-2004]
(1) a mixture of phenol and Mg(Me)Br (2) a mixture of anisole and Mg(OH)Br
(3) a mixture of benzene and Mg(OMe)Br (4) a mixture of toluene and Mg(OH)Br
(1) Ethylene (2) Acetylene (3) Diethyl ether (4) Ethyl-hydrogen sulphate
6. An unknown alcohol is treated with the "Lucas reagent" to determine whether the alcohol is primary, secondary or tertiary.
Which alcohol reacts fastest and by what mechanism - [JEE-Main- 2013]
8. The most suitable reagent for the conversion of R – CH2 – OH R – CHO is : [JEE-Main- 2014]
(1) CrO3 (2) PCC (Pyridinium Chlorochromate)
(3) KMnO4 (4) K2Cr2O7
ANSWER-KEY
Qus. 1 2 3 4 5 6 7 8
Ans. 1 2 1 3 2 2 1 2