Solve
Guides
0
You visited us 0 times! Enjoying our articles? Unlock Full Access!
Standard XI
Chemistry
Structural Representations of Organic Compounds
Question

An aromatic compound $$(A), C_{9}H_{12}O$$ was subjected to a series of test in the laboratory. It was found that this compound:
(i) does not form silver mirror with Tollens' reagent.
(ii) rotates the plane of polarised light.
(iii) reacts with sodium metal to evolve hydrogen gas.
(iv) does not decolourise pink colour of bromine water.
(v) reacts with hot $$KMnO_{4}$$ to form monocarboxylic acid $$'B'$$ which on decarboxylation gives benzene.
(vi) reacts with Lucas reagent in about $$5$$ min.
(vii) reacts with $$I_{2}$$ and $$NaOH$$ to produce yellow coloured precipitate of the compound $$(C)$$.
(viii) loses its optical activity due to formation of compound $$(D)$$ on reaction with Red $$P$$ and $$HI$$.
Answer the following questions:
Structure of the compound $$(A)$$ will be

A
B
C
D
Open in App
Solution
Verified by Toppr

Correct option is B.

Was this answer helpful?
0
Similar Questions
Q1
An unknown organic compound (A) with the molecular formula C9H12O does not decolourize Br2 in CCl4, reacts with sodium to give a colourless, odourless gas and can be oxidised by hot alkaline KMnO4 to give benzoic acid. Then, following test were performed on the compound (A) is given sequence:
Test (a): The colour of the solution changes from orange to green when K2Cr2O7 is added to it.
Test (b): The compound can be resolved.
Test (c): No yellow precipitate of CHl3 is formed when reacted with l2 and OH−.
Test (d): Oxidation of the compound with CrO3 in pyridine gives another compound that gives Tollen's test.

Which of the following would not be the structure of compound (A) after test (b)?
View Solution
Q2
An unknown organic compound (A) with the molecular formula C9H12O does not decolourize Br2 in CCl4, reacts with sodium to give a colourless, odourless gas and can be oxidised by hot alkaline KMnO4 to give benzoic acid. Then, following test were performed on the compound (A) is given sequence:
Test (a): The colour of the solution changes from orange to green when K2Cr2O7 is added to it.
Test (b): The compound can be resolved.
Test (c): No yellow precipitate of CHl3 is formed when reacted with l2 and OH−.
Test (d): Oxidation of the compound with CrO3 in pyridine gives another compound that gives Tollen's test.

The structure assigned to compound (A) after the test (d) would be
View Solution
Q3
Compound (A) reacts with [Cu(NH3)2]+ and Tollens reagent, but after reaction with alc. KOH it does not give the above test. Compound (A) is:
View Solution
Q4
A compound having formula C4H10 does not react with sodium but hydrolyzed with dil H2SO4 to form 'B'. The compound 'B' react with 'red' P and Iodine to form compound 'C'. The compound 'C' is also formed when it react and compound 'A'. Identify compound A, B and C.
View Solution
Q5
An organic compound (A) with molecular formula C8H8O forms an orange-red precipitate with 2,4−DNP reagent and gives yellow precipitate on heating with iodine in the presence of sodium hydroxide. It neither reduces Tollens' or Fehling's reagent, nor does it decolourise bromine water or Baeyer's reagent. On drastic oxidation with chromic acid, it gives a carboxylic acid (B) having molecular formula C7H6O2. Identify the compounds (A) and (B) and explain the reactions involved.

View Solution