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Organic Synthesis And Named Reactions Mock Tests

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Organic Synthesis And Named Reactions Mock Test 1

Questions: 28

नमूना प्रश्न

GATE Chemistry
The Mitsunobu reaction of (R)-1-phenylethanol with benzoic acid using triphenylphosphine and diethyl azodicarboxylate (DEAD) proceeds with:
A Retention of configuration, forming (R)-1-phenylethyl benzoate
B Inversion of configuration, forming (S)-1-phenylethyl benzoate
C Racemization, giving a racemic mixture of 1-phenylethyl benzoate
D Rearrangement, forming phenylacetate
GATE Chemistry
The electrocyclic ring opening of cis-3,4-dimethylcyclobutene under thermal conditions gives which stereoisomer of 1,3-butadiene?
A (E,Z)-1,3-dimethylbutadiene
B (E,E)-1,3-dimethylbutadiene
C (Z,Z)-1,3-dimethylbutadiene
D 1,3-Butadiene without methyl groups
GATE Chemistry
Which of the following compounds undergoes nucleophilic aromatic substitution (NAS, S_NAr) with sodium methoxide (NaOCH₃) in methanol at the fastest rate? (Consider the mechanism of S_NAr, which proceeds via a Meisenheimer complex intermediate. Electron-withdrawing groups, especially at ortho and para positions, stabilize the anionic intermediate and accelerate the reaction.)
A 1-chloro-2,4-dinitrobenzene
B 1-chloro-4-nitrobenzene
C Chlorobenzene
D 1-chloro-4-methylbenzene
GATE Chemistry
The Heck coupling of styrene with an aryl halide Ar-X gives predominantly which product?
A Ar-CH=CH₂ (biaryl)
B Ar-CH=CH-Ar (trans-stilbene derivative)
C Ar-CH₂-CH₂-Ar
D Ar-CO-CH₃
GATE Chemistry
The Wittig reaction of benzaldehyde (C₆H₅CHO) with methyltriphenylphosphonium bromide in the presence of a strong base (n-butyllithium, n-BuLi) yields which product? (The reaction involves deprotonation of the phosphonium salt to form a phosphonium ylide, followed by nucleophilic addition to the carbonyl and formation of an oxaphosphetane intermediate.)
A C₆H₅CH=CH₂ (styrene) + triphenylphosphine oxide + HBr
B C₆H₅CH₂CH₂OH (benzyl alcohol)
C C₆H₅COCH₃ (acetophenone)
D C₆H₅C≡CH (phenylacetylene)
GATE Chemistry
The Wolff-Kishner reduction converts aldehydes and ketones to alkanes using which reagent system?
A Zn(Hg) and concentrated HCl
B NH₂NH₂ and KOH (or NaOH) at high temperature
C LiAlH₄ in ether
D H₂ with Pd/C catalyst
GATE Chemistry
The Heck coupling reaction between bromobenzene and methyl acrylate (methyl propenoate, CH₃OOC−CH=CH₂) catalysed by Pd(OAc)₂ with triphenylphosphine and a base (Et₃N) yields which major product? (Consider the regioselectivity of the migratory insertion step and the preference for forming the more stable trans (E) alkene.)
A Methyl (E)-cinnamate (methyl (E)-3-phenylprop-2-enoate)
B Methyl 3-phenylpropanoate
C Methyl (Z)-cinnamate (methyl (Z)-3-phenylprop-2-enoate)
D Methyl 2-phenylacrylate
GATE Chemistry
The crossed aldol condensation between benzaldehyde (C₆H₅CHO) and acetone (CH₃COCH₃) in the presence of aqueous NaOH, followed by heating, primarily yields:
A dibenzylideneacetone (1,5-diphenylpenta-1,4-dien-3-one)
B benzyl alcohol and sodium acetate
C benzoic acid and propan-2-ol
D benzalacetone (4-phenylbut-3-en-2-one) only

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