Chemistry Test 3 with solutions

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10. The order of reactivity of halogens towards halogenation of alkanes is

11. The chlorination of alkane involves

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10. The order of reactivity of halogens towards halogenation of alkanes is

11. The chlorination of alkane involves

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September 5, 2022 admin Off Uncategorized

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Illustration 1: Which one of the following does not of dissolve in conc. H₂SO₄?

(A) CH₃ – C = C – CH₃ (B) CH₃ – CH₂ – C º CH

(C) CH º CH (D) CH₂ = CH₂

Solution: If CH º CH were to dissolve in H₂SO₄ a bisulphite salt of vinyl carbocation H₂C = C⁺H would be formed. The more s-character in the positively charged ‘C’ less stable is the carbocation and less likely to be formed.

\(C)

Illustration 2: Which one of the following compounds will give in the presence of peroxide a product different from that obtained in the absence of peroxide?

(A) 1-butane (B) 1-butene, HBr

(C) 2-butene, HCl (D) 2-butene, HBr

Solution: Peroixde effect is observed when unsymmetrical alkene is treated with HBr only (and not with HCl and HI).

\(B)

Illustration 3: Which of the following alkene on acid catalysed hydration form 2-methyl propan-2-ol.

(A) (CH₃)₂CH = CH₂(B) CH₃ – CH = CH₂

(C) CH₃ – CH = CH – CH₃ (D) CH₃ – CH₂ – CH = CH₂

Solution: Addition of H₂O occurs according to Markownikoff’s rule.

\ (A)

Illustration 4: Which of the following compounds yields only one product on monobromination?

(A) Neopentane (B) Toluene

(C) Phenol (D) Aniline

Solution: CH₃ – CH₃ has twelve equivalent 1°H. Hence H forms only one product on monobromination.

\(A)

Illustration 5: Aqueous solution of the following compounds are electrolysed. Acetylene gas is obtained from.

(A) Sodium fumarate (B) Sopdium maleate

(C) Sodium succinate (D) Both (A) and (B)

Solution:

\ (D)

Illustration 6: Dehydration of butan-2-ol with conc. H₂SO₄ gives preferred product.

(A) but-1-ene (B) but-2-ene

(C) propene (D) ethane

Solution: CH₃ – – – CH₃ CH₃ – CH = CH – CH₃ (80%)

+ CH₃ – CH₂ – CH = CH₂ (20%)

This is in accordance with saytzeff rule.

\ (B)

Illustration 7: CH₃ – C º C – CH₃ ‘X’. What is X

(A) CH₃CH₂CH = CH₂ (B) CH₃CH₂C º CH

(C) CH₃ – CH = CH – CH₃ (D) CH₂ = C = CH – CH₃

Solution: Isomerisation occurs, when 2-butyne is treated with NaNH₂, it converts into terminal alkyne (1-butyne).

\ (B)

Illustration 8: Identify the compound ‘Y’ in the following sequence of reaction

HC º CH

*(A)*		*(B)*
*(C)*		*(D)*	*CH₃COOH*

Solution:

\ (A)

Illustration 9: Dehydration of 1-butanol gives 2-butene as a major product, by which of the following intermediate the compound 2-butene obtained

*(A)*			*(B)*
*(C)*			*(D)*
*Solution:*

\ (C)

Illustration 10: The principal organic compound formed in the reaction

CH₂ = CH(CH₂)₈COOH + HBr …………. is

(A)	CH₃ –– (CH₂)₈COOH	(B)	CH₂ = CH(CH₂)₈COBr
(C)	–CH₂(CH₂)₈COOH	(D)	CH₂ = CH(CH₂)₇ – – COOH

Solution: Follows the peroxide effect

\ CH₂ = CH(CH₂)₈COOH – CH₂(CH₂)₈COOH

\ (C)

*Illustration 11:*
*(A)*			*(B)*
*(C)*			*(D)*

Solution: Probability selectivity

\ (B)

Illustration 12: The reactivity order of alkyl halides is 3° > 2° > 1° in

(A) Both S_N1 and S_N2 (B) both S_N2 and E₂

(C) Both E₁ and S_N2 (D) Both S_N1 and E₂

Solution: For S_N1, E₁ and E₂ reactivity order is 3° > 2° > 1°

\ (D)

Illustration 13: How many optically active isomers of monochloride can be obtained from 2-methyl butane

(A) 1 (B) 2

(C) 3 (D) 4

Solution: Two chiral centre generates

\ (B)

*Illustration 14:*
*(A)*			*(B)*
*(C)*			*(D)*
*Solution:*

\ (B)

Illustration 15: The following in order of leaving group capability

F^–(I), CF₃SO₃⁼(II), ^–OH(III), I^–(IV)

(A) I < III < IV < II (B) III < I < IV < II

(C) II < III < IV < I (D) IV < III < I <II

Solution: Weaker the base good is the leaving group

\ (A)

*Illustration 16:*
*(A)*			*(B)*
*(C)*			*(D)*

Solution: Protonation occurs on doubled bon

\ (B)

Illustration 17:

For the above reaction which of the following statement is not correct

(A) Rate = K[Alcohol] [SOCl₂]

(B) In the product inversion of configuration also takes place

(C) This reaction is an example of S_N2

(D) In the product retention of configuration takes place

Solution: Normal S_N2 attack

\(D)

*Illustration 18:*
*(A)*			*(B)*
*(C)*			*(D)*

Solution: Anti-dehalogenation takes place

\ (A)

Illustration 19: When isopropyl alcohol vapours are passed over heated copper it gives

(A) Acetone (B) Ethyl alcohol

(C) Methyl alcohol (D) Acetaldehyde

Solution: (CH₃)₂CHOH CH₃COCH₃

\ (A)

Illustration 20: Glycerol on treatment with oxalic acid at 110°C forms

(A) Formic acid (B) CO₂ and CO

(C) Allyl alcohol (D) Glycol

Solution: – – + H₂SO₄ ¾® HCOOH + CO₂ + glycerol

Illustration 21: CH₃OH + PCl₃ ¾® P, P is

(A) CH₄ (B) CH₃Cl

(C) CH₃COCl (D) (CH₃)₂^·

Solution: (B)

Illustration 22: Dehydration of ethanol gives

(A) CH₃COOH (B) C₂H₆

(C) C₂H₂ (D) C₂H₄

Solution: C₂H₄

\ (D)

Illustration 23: The compound that will react most readily with NaOH to form methanol is

(A) (CH₃)₄N⁺I^– (B) CH₃OCH₃

(C) (CH₃)₃S⁺I^– (D) (CH₃)₃CCl

Solution: (CH₃)₄N⁺I^– (CH₃)₃ N + CH₃OH

\ (A)

Illustration 24: – + Pb(OAc)₄ ¾® P?

(A) Oxalic acid (B) Glyoxal

(C) HCHO (D) Glycollic acid

Solution: (CH₂OH)₂ 2HCHO

\ (C)

Illustration 25: Glycerol + Conc. H₂SO₄ ¾® ?

(A) Acrolein (B) Formic acid

(C) Allyl alcohol (D) CH₃NC

Solution: CH₂OH – – CH₂OH

\ (A)

Illustration 26: Mild oxidation of 2-propanol yields

(A) CH₃COOH (B) CH₃COCH₃

(C) CH₃CH₂CHO (D) CH₃CH₂CH₂OH

Solution: CH₃COCH₃

\ (B)

\ (A)

Illustration 28: A + Ca(OCl)Cl ¾® CHCl₃. A is

(A) C₂H₆ (B) C₂H₅OH

(C) C₂H₂ (D) CH₃COOH

Solution: Molecule should contain or CH₃ –– group to then haloform reaction

\ (B)

*Illustration 29:*
*(A)*			*(B)*
*(C)*			*(D)*

Solution: Haloform reaction followed by acidification makes a b-keto acid which on heating decarboxy lates.

\ (B)

*Illustration 30:*
*(A)*			*(B)*
*(C)*			*(D)*

Solution: Intramolecular cannzaro reaction.

\ (B)

Illustration 31: A ketone reacted with C₂H=5MgBr reagent followed by hydrolysis gave a product which on dehydrationi gives an alkene. The alkene on oznolysis gave diethyl ketone and acetaldehyde. The ketone is

(A) Dimethyl keton (B) Ethyl methyl ketone

(C) Diethyl ketone (D) Ethyl propyl ketone

*Solution:*
*Illustration 32:*
*(A)*
*(B)*
*(C)*
*(D)*

Solution: Intramolecular aldol condensation

\ (B)

*Illustration 33:*
*(A)*			*(B)*
*(C)*			*(D)*

Solution: First stable carbocation is formed. Then pH group migrates.

\ (A)

*Illustration 34:*
*(A)*			*(B)*
*(C)*			*(D)*
*Solution:*
*Illustration 35:*
*(A)*			*(B)*
*(C)*			*(D)*

Solution: Caranian is formed adjacent to carbonyl group, then NGP takes place

\ (C)

*Illustration 36:*
*(A)*			*(B)*
*(C)*			*(D)*

Solution: F.C. acylation followed by oxidation. SeO₂ Oxides – CH₂ – group adjaenet (B) top carbonyl group to

\ (B)

Illustration 37: Among the following which compound does not give iodoform test.

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

Solution: (D)

*Illustration 38:*
*(A)*			*(B)*
*(C)*			*(D)*

Solution: Cannizaro reaction takes place

\ (C)

Illustration 39: On strong heating ammonium acetate gives

(A) methyl cyanide (B) acetamide

(C) urea (D) form amide

Solution: B

Illustration 40: The product (B) in the following reaction is

Acetamide A

(A) CH₃NH₂ (B) C₂H₅NH₂

(C) CH₃CN (D) CH₃COONH₄

Solution: B

Illustration 41: Weakest acid among the following is

(A) CH₃COOH (B) ClCH₂COOH

(C) HCCl₂COOH (D) Cl₃C.COOH

Solution: A

Illustration 42: Formic acid and formaldehyde can be distinguished by treating with

(A) Benedict’s solution (B) Tollen’s reagent

(C) Fehling’s solution (D) NaHCO₃

Solution: D

Illustration 43: The product (Y) in the following reaction is

C₆H₅CH₂Cl

(A) Benzoic acid (B) Phenol

(C) Toluene (D) Benzaldehyde

Solution: D

Illustration 44: (X) Benzotrichloride

(X) and (Y) are respectively

(A) Benzene, benzaldehyde (B) Toluene, benzaldehyde

(C) Toluene, benzoic acid (D) Benzene, benzoic acid

Solution: C

Illustration 45: Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halides due to

(A) The formation of less stable carbonium ion

(B) Resonance stabilization

(C) Lower carbon-halogen bond

(D) Inductive effect

Solution: B

Illustration 46: Chlorination of toluene in presence of light and heat followed by treatment with aqueous NaOH gives

(A) o-Cresol (B) p-cresol

(C) 2,4- dihydroxy toluene (D) Benzoic acid

Solution: D

Illustration 47: Benzoic acid when treated with PCl₅ gives

(A) Chlorobenzene (B) Benzyl chloride

(C) Benzoyl chloride (D) Benzene

Solution: C

Illustration 48: Which one of the following compound forms benzoic acid on oxidation?

(A) Chlorophenol (B) Benzyl chloride

(C) Chlorobenzene (D) Chlorotoluene

Solution: B

Illustration 49: Phenyl diazonium does not form azodye with

(A) aniline (B) phenol

(C) N,N-dimethylaniline (D) anisole

Solution: D

Illustration 50: Identify (C) in the following reaction sequence

CH₃NH₂

(A) CH₃CH₂CH₂NH₂ (B) (CH₃)₃N

(C) (CH₃)₂NH (D) (CH₃)₄

Solution: B

Illustration 51: The reagent (X) is

C₆H₅CH₂CONH₂ C₆H₅CH₂CN

(A) P₂O₅ (B) SOCl₂

(C) POCl₃ (D) All the above

Solution: D

Illustration 52: Melamine polymer is a copolymer of

(A) melamine and acetaldehyde (B) melamine and formaldehyde

(C) phenol and formaldehyde (D) None of the above

Solution: B

Illustration 53: Identify (Z)

C₆H₁₃COCl

(A) C₆H₁₃CH₂NHC₆H₁₃ (B) C₁₂H₂₅CH₂NH₂

(C)

(D)

(C₆H₁₃)₂CH₃N

Solution: A

Illustration 54: Which of the following will give a positive carbylamine test

H₃CNH₂ 2. CH₃NHCH₃ 3. (CH₃)₃N 4. C₆H₅NH₂

(A) 1 and 3 (B) 2 and 4

(C) 3 and 4 (D) 1 and 4

Solution: D

Illustration 55: Which of the reagent is not used to convert nitrobenzene to aniline

(A) H₂/Ni (B) Sn+HCl

(C) SnCl₂ in HCl (D) LiAlH₄

Solution: D

Illustration 56: Which one of the following HHa fdasfkladjfdajf dk

is produced by the reduction of RCN in sodium and alcohol

(A) RCONH₂ (D) RCO-NH₄⁺

(C) RCH₂NH₂ (D) (RCH₂)₃N

Solution: C

Illustration 57: In the following reaction, the product (X) is

CHCl₃+PhNH₂ ¾¾® X + 3Y + 2Z

(A) PhCN (B) PhNC

(C) PhCl (D) PhOH

Solution: B

Illustration 58: Which of the following is weakest base in water

(A) Aniline (B) p-nitoroaniline

(C) Trimethylaniline (D) ammonia

Solution: B

Hydrocarbons

Point out (A) in the given reaction sequence:

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

End product of the following sequence is:

(A) Ethanol (B) Ethyl hydrogen sulphate

10 mL of a certain hydrocarbon require 25 mL of oxygen for complete combustion and the volume of CO₂ product is 20 mL. What is the formula of hydrocarbon.

(A) C₂H₂ (B) C₂H₄

Hydrogenation of the compound:

In the presence of poisoned palladium catalyst gives:

(A) An optically active compound (B) An optically inactive compound

5.
(A)			(B)
(C)			(D)

CH₃ –– CH = CH₂ + HBr ¾® A (predominant), A is

	(A)	(B)
	(C)	(D)	None is correct
7.

In the increasing order is

(A) I < III < IV < II (B) I < II < III < IV

Which is true about this reaction?

(A) A is meso 1, 2-butan-di-ol formed by syn addition

(B) A is meso 1, 2-butan-di-ol fomred by anti addition

(D) A is a racemic mixture of d and l 1, 2-butan-di-ol formed by syn addition.

9 The treatment of C₂H₅MgI with water produces

(A) Methane (B) Ethane

(A) F₂ > Br₂ > Cl₂ (B) F₂ > Cl₂ > Br₂

(A) Cl free radicals (B) Cl⁺ species

12.

(A)

Which is true statement?

(A) A is formed by anti addition and is meso

(B) A is formed by syn addition and is meso

(D) A is formed by syn addition and is racemic

13.

(A) cis (B) trans

(A) cis-2-butene

(B) trans-2-butene II

Correct statements are

(A) is racemic mixture by anti addition

(B) II is meso compound by anti addition

(D) II is racemic compound by syn addition

15.

A and B are

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

Alkyl Halide

16.
(A)			(B)
(C)			(D)

(CH₃)₃CMgCl A. A is

(A) (CH₃)₃CD (B) (CD₃)₃CD

RMgBr

(A) RCO₃H (B) RCO₂H

Addition of HCl to propene involves

(A) CH₃CH₂Cl (B)

20.
(A)			(B)
(C)			(D)

1-methyl cyclohexene can be converted to 2-methyl 1-cyclohexanol by

(A) Acid catalysed hydration (B) Hydroboration

Which of the following is the best leaving group?

(A) OAc^–(B) CF₃SO₃^–

Which of the following alcohol can be dehydrated must easily?

(A) CF₃CH₂OH (B) CF₃(CH₂)₂OH

Which of the following does not give ppt. with alcoholic AgNO₃

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

In S_N1 reaction recemisation occurs because of

(A) Carbocation formation (B) Carbanion formation

The halide which undergoes nucleophilic substitution most readily is

(A) p-CH₃C₆H₄Cl (B) o-H₃COC₆H₄Cl

Best starting material to synthesize 2-methyl 2-butanoic acid is

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

On conversion into grignard followed by treatment with ethanol, how many alkyl halides would yield and methyl butane.

(A) 2 (B) 3

In protic medium the strongest ncuelphilie is

(A) Cl^– (B) F^–

Which one is the strongest base?

(A) C^–H₃ (B) ^–NH₂

Alcohols, Ethers and Phenols

For the preparation of t-butylmethyl ether the correct choice of reagent is

(A) Methoxide and t-butyl bromide (B) Methanol and 2-bromobutane

32.
(A)	(B)
(C)	(D)
33.
(A)	(B)
(C)	(D)
34.
(A)	(B)
(C)	(D)
35.
(A)	(B)
(C)	(D)
36.
(A)	(B)
(C)	(D)
37.
(A)	(B)
(C)	(D)	None of these
38.
(A)	(B)
(C)	(D)	None of these
39.

(A) Anisole (B) Phenetole

40.
(A)			(B)
(C)			(D)

Carbonyl Compounds

Cyclohexanone on reaction with Na₂CO₃ solution forms

(A)			(B)
(C)			(D)
42.
(A)			(B)
(C)			(D)

Cannizaro reaction is given by

(A) Trimethylacetaldehyde (B) Acetaldehyde

Haloform reaction is not shown by

(A) CH₃COCH₃ (B) C₂H₅OH

Ozonolysis of 2-methylbut-2ene yields

(A) Aldehyde only (B) Ketone only

46. Which of the following reagents does not react with HCHO, CH₃CHO and CH₃COCH₃ respectively, in the same manner?

(A) HCN (B) NH₂OH

Products

(A) HCHO + 4HCOOH (B) 4HCHO + HCOOH

Which of the following does not undergo aldol condensation?

(A) PhCH₂CHO (B) PhCHO

A new carbon-carbon bond formation is possible

(A) Cannizaro reaction (B) Friedal Craft reaction

Which of the following will react with water most readily?

(A) CHCl₃ (B) Cl₃CCHO

Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is

(A) MeCOCl (B) MeCHO

In a Cannizaro reaction the intermediate that will be the best hydride donor is

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

In the transformation

The reagent is

(A) Zn/Hg conc. HCl (B) NH₂NH₂, OH^–

Which of the following will decarboxylate on heating?

(A) PhCOCOOH (B) PhCOCH₂COOH

In Cannizzaro reaction given below

2Ph – CHO PhCH₂OH + PhCO₂^–

the slowest step is

(A) Attack of OH^– at the carbonyl group

(B) Transfer of hydride to carbonyl group

(D) Deprotonation of Ph – CH₂OH

Carboxylic Acids and its Derivatives

When sodium formate is heated at 360°C, the main product is

(A) Sodium oxalate (B) CO

Sodium acetate on reaction with acetyl chloride gives

(A) CH₃COOH (B) Sodium formate

When sodium formate is heated with soda lime it forms

(A) H₂ (B) CH₄

When formic acid reacts with PCl₅, it forms

(A) acetyl chloride (B) formyl chloride

When formic acid is heated with conc. H₂SO₄ it gives

(A) CO₂ (B) CH₃HSO₄

Which one of the following be expected to be most highly ionized in water

(A) CH₂ClCH₂CH₂COOH (B) CH₃CHClCH₂COOH

Mercuric chloride is reduced to mercurous chloride by

(A) acetic acid (B) Carbon tetrachloride

The end product in the following sequence is

CH₃OH

(A) HCOOH (B) CH₃COOH

Oxalic acid on treatment with conc. H₂SO₄ gives

(A) CO+H₂O₂ (B) HCOOH+CO₂

The product (C) in the reaction is

RCOOH

(A) RNH₂ (B) RCN

Which of the following cannot reduce Fehling’s solution?

(A) Formic acid (B) acetic acid

Formic acid and acetic acid can be distinguished with

(A) Litmus paper (B) Caustic soda

RCOOH ¾¾¾® RCH₂OH

This conversion can be affected by

(A) Zn/HCl (B Na/C₂H₅OH

Acetic acid reacts with chlorine in the presence of catalyst anhyd FeCl₃ to give

(A) acetyl chloride (B )methyl chloride

The product (X) of the reaction is

CH₃CONH₂ + HNO₂ ¾¾® (X)

(A) CH₃NH₂ (B) CH₃CH₂NH₂

Amines

When aniline is treated with fuming sulphuric acid at 475 K it gives

(A) Sulphanilicacid (B) aniline sulphate

When aniline is treated with bromine water it forms

(A) 2–bromoamiline (B) 4-bromoaniline

Hydrolysis of phenyl isocyanide forms

(A) Benzoic acid (B) Formic acid

Towards electrophilic substitution, the most reactive species be

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

Acid hydrolysis of benzonitrile forms

(A) benzylamine (B) aniline

For selective reduction of m-dinitrobenzene to m- nitroaniline, the reducing agent is

(A) Sn/HCl (B) Zn/NH₄Cl(aq)

Aniline on reaction with acetyl chloride forms

(A) phenol (B) acetamide

For the conversion of primary amide to amine having same number of carbons, the reagent will be

(A) Br₂+NaOH (B) LiAlH₄

Which of the following is not correct regarding aniline?

(A) It is less basic than ethylamine (B) It can be steam-distilled

(C It reacts with sodium to give hydrogen (D) It is soluble in water

Which of the following reagents will give methylamine from acetamide

(A) PCl₃ (B) NaOH+Br₂

The compound which on reaction with aq. nitrous acid at low temperature produces oily nitrosamine is

(A) methylamine (B) ethylamine

The correct order of b.p of the following amines is
n-butylamine 2. Ethyldimethyl amine 3.diethylamine

(A) 1>3>2 (B) 1>2>3

The conjugate acid of HO(CH₂)₃ NH₂ is

(A) H₂O⁺(CH₂)₃ NH₂ (B) HO(CH₂)₃

Place the following aromatic amines in the decreasing order of their basicities
PhNH₂ 2.Ph₂NH 3.Cyclohexyl-NH₂

(A) 3>1>2 (B) 3>2>1

Identify (Z)

C₆H₅COOH (X)

(A) C₆H₅CH₂NH₂ (B) C₆H₅CH₂CH₂NH₂

Hydrocarbons

C 2. C
A 4. B
B 6. C
A 8. A
B 10. B
A 12. A
A 14. C, D
D

Alkyl Halides

A 17. A
B 19. D
A 21. B
B 23. D
D 25. A
D 27. C
C 29. D
A

Alcohols, Ethers and Phenols

D 32. D
D 34. D
D 36. A
C 38. A
C 40. C

Carbonyl Compounds

A 42. A
A 44. C
C 46. D
A 48. B
B 50. B
A 52. C
A 54. B
A

Carboxylic Acids and its Derivatives

A 57. C
A 59. B
D 61 D
C 63. B
D 65. B

66 B 67. D

D 69. C
C

Amines

A 72. D
B 74. B
C 76 C
B 78. B
D 80. B

81 C 82. A

B 84. A
B

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Illustration 27:

None of these

Solution: