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Chapter 2: Problem 193

Identify the correct statement among the following. (a) A hydrocarbon of M.F. \(\mathrm{C}_{6} \mathrm{H}_{12}\) on reductive ozonolysis gave only one product which fails to react with Tollens reagent. The hydrocarbon could be 2,3 dimethyl but- 2 -ene. (b) Addition of bromine to trans-2-butene gives a racemic mixture of two optically active enantiomers. (c) But-1-yne and but-2-yne can be distinguished using ammoniacal cuprous chloride. (d) Ozonolysis of acetylene gives glyoxal.

Short Answer

Expert verified
a) 2,3-dimethyl but-2-ene does not react with Tollens reagent. b) The addition of bromine to trans-2-butene leads to the formation of optically active enantiomers. c) Ammoniacal cuprous chloride can be used to differentiate between but-1-yne and but-2-yne. d) Ozonolysis of acetylene would give glyoxal as the product. Answer: (c) and (d) are the correct statements.

Step by step solution

01

Statement (a) Evaluation

Reductive ozonolysis involves the breakdown of a double Bond in organic compounds, followed by the addition of hydrogen to form different products. The given molecular formula is \(\mathrm{C}_{6} \mathrm{H}_{12}\). The product fails to react with Tollens reagent (which detects aldehydes), so it must not be an aldehyde. Therefore, the given hydrocarbon, 2,3-dimethyl but-2-ene, could be an accurate option.
02

Statement (b) Evaluation

trans-2-Butene is an alkene with a double bond between carbons 2 and 3. Addition of bromine to trans-2-butene leads to the formation of a dibromo product. Since the original trans-2-butene molecule is symmetric and has no chiral centers, the dibromo product formed should also have no chiral centers. Therefore, there will not be any optically active enantiomers formed. This statement is incorrect.
03

Statement (c) Evaluation

But-1-yne and but-2-yne are alkynes with triple bonds between carbons 1-2 and 2-3, respectively. Ammoniacal cuprous chloride (Cu\(_2\)Cl\(_2\)) is used to differentiate terminal and internal alkynes since it reacts with terminal alkynes only, forming a red precipitate of copper acetylide. But-1-yne being a terminal alkyne would react with ammoniacal cuprous chloride while but-2-yne (an internal alkyne) would not. This statement is correct.
04

Statement (d) Evaluation

Ozonolysis of acetylene (\({C_2H_2}\)) involves breaking the triple bond and formation of a carbonyl group at each carbon atom. Since there are two carbon atoms, the resulting molecule would have 2 carbonyl groups and the molecular formula \({C_2H_2O_2}\). This molecule is called glyoxal. Therefore, this statement is also correct. In conclusion, statements (c) and (d) are the correct statements among the given options.

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Most popular questions from this chapter

This section contains multiple choice questions. Each question has 4 choices (a), (b), (c) and (d), out of which ONLY ONE is correct. A compound with the molecular formula, \(\mathrm{C}_{4} \mathrm{H}_{6}\), does not exist in cis or trans form. It does not produce a precipitate with ammoniacal \(\mathrm{AgNO}_{3}\) solution. The compound as such is optically inactive but a monohalogen derivative can be optically active. The compound is (a) \(\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{C}=\mathrm{CH}_{2}\) (c) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{C} \equiv \mathrm{C}-\mathrm{H}\) (d)

An alkene on reductive as well as oxidative ozonolysis gave only one product. The alkene is (a) propene (b) 2,3-dimethyl-2-butene (c) pent-2-ene (d) 2 -methyl propene

Reaction of trans-2-phenyl-1-bromocyclohexane with hot alcoholic \(\mathrm{NaOH}\) gives (a) 3 -phenylcyclohexene (b) 1 -phenylcyclohexene (c) 2 -bromophenyl cyclohexane (d) 2 -phenyl cyclohexanol

The number of structural and stereoisomers of a bromo compound \(\mathrm{C}_{5} \mathrm{H}_{9} \mathrm{Br}\) formed by the addition of \(\mathrm{HBr}\) to pent- 2 yne are respectively (a) 4 and 2 (b) 1 and 2 (c) 2 and 4 (d) 2 and 1

What are the products formed when buta-1, 3 -diene is treated with HBr in \(1: 1\) molar proportion? Explain the formation of the products.
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