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NEET-CRASH-2017 CHEMISTRY TEST

ALDEHYDES, KETONES, ACIDS-01-170419


1. Which of the following on heating with aqueous KOH, produces acetaldehyde
a) CH3CH2Cl b) CH2Cl.CH2Cl c) CH3CHCl2 d) CH3COCl
2. The photochemical bromination of ethylbenzene with excess of bromine followed by hydrolysis
with aqueous KOH gives
a) PhCHO b) PhCH2CHO c) PhCOCH3 d) PhCHOHCH3
3. COCl
H2
'A'
Pd - BaSO4

The product ‘A’ is


a) C6H5COCH3 b) C6H5Cl c) C6H5CHO d) C6H5OH
4. The product (A) and (B) in the following reactions respectively are
PhCH = CH2 ⎯⎯⎯⎯⎯ → (A) ⎯⎯⎯⎯ → (B)
2 4(i) Br /CCl
2 4 Dil.H SO
(ii) NaNH2 /liq.NH3 HgSO4

a) PhCH2CHO, PhCH2CH2OH b) PhC  CH, PhCOCH3


c) PhC  CH, PhCH2CHO d) PhCH2CH2CH3, PhCOCHO
5. Which of the following alkenes is most suitable for the preparation of butanone by ozonolysis

a) b) c) d)
6. In the following reaction sequence,
CH3CH2Br ⎯⎯⎯⎯→ (A) ⎯⎯⎯⎯⎯⎯⎯→ (B)
KCN (alc)2 2 (i)SnCl /HCl,Et O
 (ii) H 2 O,heat

The final product (B) is


a) CH3CH2CHO b) CH3CH2CH2NH2 c) CH3CH2CONH2 d) CH3CH2COOH
7. Which of the following compounds on hydroboration-oxidation gives pentanal as the major
product?
a) Pent-1-ene b) Pent-2-ene c) Pent-2-yne d) Pent-1-yne
8. The most suitable reagent for conversion of RCOOC2H5 → RCHO is
a) LiAlH (O-t-Bu)3 b) DIBAL-H c) SnCl 2/HCl d) NaBH3CN
9. Which of the following is the best method for the preparation of acetophenone?
a) PhCOOEt + CH3MgBr b) PhCOCl + CH3MgBr
c) PhCONH2 + CH3MgBr d) PhCN + CH3MgBr
10. p-cresol reacts with chloroform in alkaline medium to give the compound A which adds
hydrogen cyanide to form the compound B. The latter on acidic hydrolysis gives chiral
carboxylic acid. The structure of the carboxylic acid is
CH3 CH3
CH(OH)COOH

CH(OH)COOH

a) OH b) OH

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CH3 CH3
CH 2COOH

CH 2COOH

c) OH d) OH
11. The formation of cyanohydrin from acetone is which type of reaction?
a) Electrophilic substitution b) Electrophilic addition
c) Nucleophilic addition d) Nucleophilic substitution
12. Arrange the following compounds in increasing order of their reactivity in nucleophilic addition
reactions. Ethanal (I), Propanal (II), Propanone (III), Butanone (IV)
a) III < II < I < IV b) II < I < III < IV c) IV < III < II < I d) I < II < III < IV
13. The correct order of reactivity of PhMgBr with
O O O
Ph C Ph H3C C H H3C C CH3

(I) (II) (III)


a) I > II > III b) III > II > I c) II > III > I d) I > III > II
14. Which of the following compounds does not react with sodium bisulphite?
a) Benzaldehyde b) Acetophenone c) Acetone d) Acetaldehyde
15. The increasing order of the rate of HCN addition to compound, A – D is
A. HCHO B. CH3COCH3 C. PhCOCH3 D. PhCOPh
a) A < B < C < D b) D < B < C < A c) D < C < B < A d) C < D < B < A
16. Which of the following is reduced with zinc and hydrochloric acid to give the corresponding
hydrocarbon?
a) ethyl acetate b) acetic acid c) acetamide d) butan-2-one
17. The conversion,

COCH 3 CH 2CH 3

can be carried out by


a) H2/Pt b) LiAlH4 c) N2H4 – KOH,  d) K2Cr2O7/H2SO4

18. A and B in the following reactions are


R OH
HCN B
R C R' A C
KCN CH 2NH 2
O R'

OH CN
, B , B +
A RR'C NH 3 A RR'C H3O
a) COOH b) OH

CN
A RR'C , B LiAlH 4
c) A = RR’CH2CN, B = NaOH d) OH

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19. The major product of the following reaction is
RCH2OH
H (anhydrous)
O

a) a hemiacetal b) an acetal c) an ether d) an ester


20. If 3-hexanone is reacted with NaBH4 followed by hydrolysis with D2O, the product will be
a) CH3CH2CH(OH)CH2CH2CH3 b) CH3CH2CD(OH)CH2CH2CH3
c) CH3CH2CH(OD)CH2CH2CH3 d) CH3CH2CD(OD)CH2CH2CH3
21. Identify the product Y in the following reaction sequence
CH 2 CH 2 COO
heat Zn - Hg
Ca X Y
CH 2 CH 2 COO HCl, heat

a) Pentane b) Cyclobutane c) Cyclopentane d) Cyclopentanone


22. In the given transformation, which of the following is the most appropriate reagent?
CH CHCOCH 3
CH CHCH 2CH 3
Reagent
HO
HO

a) Zn-Hg/HCl b) Na, liq. NH3 c) NaBH4 d) NH2 – NH2, OH-


23. Reduction with aluminium isopropoxide in excess of isopropyl alcohol is called Meerwein
Ponndorff Verley reduction (MPV). What will be the final product when cyclohex-2-enone is
selectively reduced in MPV reaction?
a) Cyclohexanol b) Cyclohex-2-enol c) Cyclohexanone d) Benzene

Aluminium tert - butoxide


A
Acetone
24. HO In the above reaction, A is

O CH3
a) b) O c) O d)
25. The product of acid hydrolysis of P and Q can be distinguished by
OCOCH 3 H3C
P H2C Q
CH3 OCOCH 3
a) Lucas reagent b) 2,4-DNP c) Fehling’s solution d) NaHSO3
26. Fehling solution will oxidise

I. CHO II. CH CH3 III. CH 2CHO IV. HCHO

OH
a) All b) Only I and IV c) Only II and III d) Only III and IV
27. 1-Propanol and 2-propanol can be distinguished by
a) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution
b) Oxidation with acidic dichromate followed by reaction with Fehling solution
c) Oxidation by heating with copper followed by reaction with Fehling solution
d) Oxidation with conc. H2SO4 followed by reaction with Fehling solution

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28. Compound ‘A’ (molecular formula C3H8O) is treated with acidified potassium dichromate to form
a product ‘B’ (molecular formula C3H6O). ‘B’ forms a shinign silver mirror on warming with
ammoniacal silver nitrate. ‘B’ when treated with an aqueous solution of H 2NCONHNH2.HCl and
sodium acetate gives a product ‘C’. Identify the structure of ‘C’
a) CH3CH2CH = NNHCONH2 b) H3C C NCONHNH 2
CH3

c) H3C C NNHCONH 2 d) CH3CH2CH = NCONHNH2


CH3
29. Which of the following compounds would not form a silver mirror with Tollens’ reagent?
a) CH3CHO b) HCHO c) R – CO – CHOHR d) CH3COCH3
30. Which of the following reactions cannot be used to prepare acetophenone?
a) Reaction of benzene with acetyl chloride in presence of anhydrous AlCl 3
b) Dry distillation of a mixture of calcium benzoate and calcium acetate
c) By the action of (CH3)2Cd on benzoyl chloride followed by acid hydrolysis
d) KMnO4 oxidation of ethylbenzene
31. Which of the following on reduction with LiAlH4 will not give ethyl alcohol?
a) (CH3CO)2O b) CH3COCl c) CH3CONH2 d) CH3COOC2H5
32. Statement 1: p-Methoxybenzaldehyde undergoes nucleophilic addition more readily than
p-nitrobenzaldehyde
Statement 2: The carbon atom of the aldehyde group is more electrophilic in p-
nitrobenzaldehyde than in p-methoxybenzaldehyde
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 true, statement 2 is false d) Statement 1 is false, statement 2 is true
33. Iodoform test is not given by
(a) 2-pentanone (b) 3-pentanone (c) ethanal (d) ethanol
34. A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives
(a) benzyl alcohol and sodium formate (b) sodium benzoate and methyl alcohol
(c) sodium benzoate and sodium formate (d) benzyl alcohol and methyl alcohol

35. A compound A (C5H10Cl2) on hydrolysis gives C5H10O which reacts with NH2OH, forms iodoform
but does not give Fehling test. A is
Cl Cl
CH 3 C CH 2 CH 2 CH3 CH 3CH 2 C CH 2CH 3
(a) (b)
Cl Cl
Cl Cl Cl

CH 3CH 2CH 2CH 2CH Cl CH 3CH CH CH CH 2CH 3


(c) (d)
36. Cyclohexanone on heating with conc. NaOH gives
OH O OH

(b) (c) (d)


(a)
HO
O O O

37. Which of the following does not undergo aldol condensation?


(a) Acetaldehyde (b) Propionaldehyde
(c) Trichloroacetaldehyde (d) Trideuteroacetaldehyde

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38. In the anion RCOO-, the two carbon-oxygen bonds are found to be of equal length. What is the
reason for it?
a) The anion is obtained by removal of a proton from the acid molecule
b) Electronic orbitals of carbon atom are hybridized
c) The C = O bond is weaker than the C – O bond
d) The anion HCOO- has two resonating structures

MgBr

(i) CO2
P
(ii) H3O+
39. In the above reaction, product ‘P’ is

CHO COOH OH

a) b) c) d) H5C6 C C6 H5

40. R – CH2 – CH2OH can be converted into RCH2CH2COOH. The correct sequence of reagents is
a) PBr3, KCN, H+ b) PBr3, KCN, H2 c) KCN, H+ d) HCN, PBr3, H+
41. Among the following acids which has the lowest pK a value?
a) CH3COOH b) HCOOH c) (CH3)2CHCOOH d) CH3CH2COOH
CH3CH2COOH ⎯⎯→ A ⎯⎯⎯⎯
→ B
Cl
42. What is B?
2 alc.KOH
Red P

a) CH3CH2COCl b) CH3CH2CHO c) CH2 = CHCOOH d) ClCH2CH2COOH

43. Carbonation of methylmagnesium bromide gives an organic compound. This compound is also
obtained by
a) hydrolysis of acetonitrile by a mineral acid
b) oxidation of methyl alcohol
c) hydrolysis of methyl isocyanide with a mineral acid
d) hydrolysis of methyl formate with dilute mineral acid
44. In a set of reactions, acetic acid yielded product D
CH3COOH ⎯⎯⎯ → A ⎯⎯⎯⎯ → B ⎯⎯⎯
→ C ⎯⎯⎯
→D
SOCl2 Benzene HCN HOH
Anhyd.AlCl3

The structure of D would be


OH COOH
C COOH CH 2 C CH3

a) CH3 b) OH

CN OH
C CH3 CH 2 C CH3

c) OH d) CN

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45. The reactive reactivates of acyl compounds towards nucleophilic substation are in the order of
a) acid anhydride > amide > ester > acyl chloride
b) acyl chloride > ester > acid anhydride > amide
c) acyl chloride > acid anhydride > ester > amide
d) ester > acyl chloride > amide > acid anhydride

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KEY ANS:
CCCBA ADBDB CCCBC DCDBC CDBCC DCADD
CDBAA DCDBA BCAAC