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Kolbe Electrolysis for Alkenes

A hydrocarbon...

Question

A hydrocarbon on ozonolysis gives one mole each of compounds $A$ and $B$ . Both $A$ and $B$ on reduction with sodium borohydride gives compounds $C$ and $D$ belonging to same homologous series. $C$ has no position isomer whereas $D$ has position isomer. $A$ and $B$ do not belong to the same homologous series. However, both $A$ and $B$ on oxidation with acidified $K M n O_{4}$ give same compound. Identify the hydrocarbon.

A

3- Methyl-2-butene

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B

2,3-Dimethyl-1-butene

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C

2-Methyl-2-butene

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D

3,4-Dimethyl-1-butene

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Solution

The correct option is C 2-Methyl-2-butene
Ozonolysis of alkenes form ketone or aldehydes. Their reduction with $N a B H_{4}$ gives alcohols. $C$ has no position isomer whereas $D$ has position isomer.Thus $C$ is a primary alcohol and $D$ is a secondary alcohol. $A$ is an aldehyde and $B$ is a ketone. And the compound is $2 - m e t h y l - 2 - b u t e n e$
$C H_{3} - (C H_{3}) C = C H - C H_{3} (O_{3}) \to C H_{3} - (C H_{3}) C = O [A] + O = C H - C H_{3} [B] N a B H_{4} \to C H_{3} - (C H_{3}) C H - O H [C] + H O - C H_{2} - C H_{3} [D] K M n O_{4} \to C H_{3} - (C H_{3}) C H - O H + H O O C - C H_{3}$

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Q. From the list of alkenes given below, identify the alkenes which on ozonolysis give only ketones.
(a) 2 methyl-1-butene
(b) 1-butene
(c) 2,3-dimethyl-2-butene
(d) 3-methyl-2-pentene
(e) 3,4-dimethyl-3- hexene
(f) 2,5-dimethyl-2,4-hexadiene

(a) What is a homologous series? Explain with an example.
(b) State two characteristics of a homologous series.
(c) The molecular formula of an organic compound is C₁₈H₃₆. Name its homologous series.
(d) Select the hydrocarbons which belong to the same homologous series. Give the name of each series.
CH₄, C₂H₂, C₂H₄, C₂H₆, C₄H₁₀, C₃H₄, C₃H₆
(e) What is meant by 'heteroatom'? Give examples. Write the names and formulae of two organic compounds containing different heteroatoms.

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