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Organic Chemistry

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90. Treatment of phenol with sodium hydroxide and then carbon dioxide gives which acid after work-up?

[AIEEE Chemistry — 2009]

(A) Benzoic acid

(B) Salicylaldehyde

(C) Salicylic acid

(D) Phthalic acid

Answer: (C) Salicylic acid

Explanation: The Kolbe–Schmitt reaction introduces a carboxyl group onto a phenoxide ring, mainly at the ortho position under suitable conditions. Acidification produces salicylic acid, also known as 2-hydroxybenzoic acid. The reaction connects aromatic phenols and important organic carboxylic acids.

89. Which liquid forms a fruity-smelling ester when mixed with ethanol and concentrated sulphuric acid?

[AIEEE Chemistry — 2009]

(A) Methanol

(B) Formaldehyde

(C) Acetone

(D) Acetic acid

Answer: (D) Acetic acid

Explanation: Acetic acid reacts reversibly with ethanol in the presence of concentrated sulphuric acid to form ethyl ethanoate and water. Ethyl ethanoate is a volatile ester with a characteristic fruity odour. Sulphuric acid catalyses the Fischer esterification reaction.

88. What is the rate-determining step of the Cannizzaro reaction of benzaldehyde?

[AIEEE Chemistry — 2009]

(A) Hydride transfer to another carbonyl molecule

(B) Removal of a proton from a carboxylic acid group

(C) Hydroxide attack on a carboxylate group

(D) Removal of the benzyl alcohol proton

Answer: (A) Hydride transfer to another carbonyl molecule

Explanation: Hydroxide first attacks the benzaldehyde carbonyl, creating a tetrahedral intermediate. The crucial slow step transfers a hydride from that intermediate to a second aldehyde molecule. This produces the reduced alcohol and an oxidised carboxylate after the subsequent proton-transfer steps.

87. What is Bisphenol A (BPA)?

[UPSC CSE Prelims — 2008]

(A) A diagnostic test for cancer

(B) A test for performance-enhancing drugs in athletes

(C) A chemical used to develop food-packaging materials

(D) A specialised steel alloy

Answer: (C) A chemical used to develop food-packaging materials

Explanation: Bisphenol A is an organic industrial compound used to produce polycarbonate plastic and epoxy resins. Certain containers and protective food-can coatings historically used these materials. BPA is not a medical test or steel alloy, and its possible hormonal effects have prompted safety scrutiny.

86. A mixture of which gases is responsible for most explosions in coal mines?

[UPSC CSE Prelims — 2008]

(A) Hydrogen and oxygen

(B) Oxygen and acetylene

(C) Methane and air

(D) Carbon dioxide and methane

Answer: (C) Methane and air

Explanation: Coal seams may release methane, a flammable hydrocarbon. When it accumulates with oxygen-containing air within an ignitable range, an ignition source can trigger a mine explosion. Ventilation and gas detection are crucial safeguards. Carbon dioxide itself does not act as a combustible fuel.

85. Reductive ozonolysis of but-2-ene with ozone followed by zinc and water gives which product?

[AIEEE Chemistry — 2008]

(A) Propanal

(B) Propanone

(C) Butan-2-one

(D) Ethanal

Answer: (D) Ethanal

Explanation: But-2-ene has a symmetrical internal double bond. Cleavage of this bond by ozone followed by a reductive work-up gives two molecules of ethanal. Ketones or larger aldehydes would require differently substituted double-bonded carbons in the starting alkene.

84. Nitration of toluene, reduction of the nitro groups, diazotisation, and treatment with cuprous bromide produces which mixture?

[AIEEE Chemistry — 2008]

(A) Ortho- and para-bromotoluene

(B) Ortho- and para-dibromobenzene

(C) Ortho- and para-bromoaniline

(D) Ortho- and meta-bromotoluene

Answer: (A) Ortho- and para-bromotoluene

Explanation: Toluene nitration initially produces mainly ortho and para derivatives. Reduction converts nitro groups to amino groups; diazotisation followed by the Sandmeyer reaction substitutes bromine for the amino-derived diazonium group. Consequently, the final mixture mainly contains ortho- and para-bromotoluenes.

83. Which statement about natural and synthetic rubber is false?

[AIPMT Chemistry — 2008]

(A) Buna-S is a butadiene-styrene copolymer

(B) Natural rubber is a 1,4-polymer of isoprene

(C) Vulcanisation forms sulphur bridges between polymer chains

(D) Natural rubber has a trans configuration at every double bond

Answer: (D) Natural rubber has a trans configuration at every double bond

Explanation: Natural rubber is predominantly cis-1,4-polyisoprene, not the trans form described in the last statement. The cis configuration contributes to elasticity. Buna-S is a butadiene-styrene copolymer, and vulcanisation forms sulphur cross-links that improve toughness and resilience.

82. Which aldehyde reacts with phenol to produce Bakelite resin?

[AIEEE Chemistry — 2008]

(A) Ethylene glycol

(B) Acetaldehyde

(C) Acetone

(D) Formaldehyde

Answer: (D) Formaldehyde

Explanation: Bakelite is a phenol-formaldehyde thermosetting resin. Reactions of phenolic aromatic sites with formaldehyde lead to methylene-linked networks that become rigid on curing. Acetone is a ketone and ethylene glycol is a diol, so neither is the standard aldehyde used for this polymer.

81. By which other name is the compound RDX known?

[UPSC CSE Prelims — 2007]

(A) Cyanohydrin

(B) Dextran

(C) Cyclohexane

(D) Cyclonite

Answer: (D) Cyclonite

Explanation: Cyclonite is a common alternative name for RDX, an energetic cyclic nitramine compound. The other options designate unrelated substances: cyanohydrins are compounds bearing hydroxyl and cyano groups, dextran is a polysaccharide, and cyclohexane is a saturated six-carbon hydrocarbon.

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