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Introduction to Alkenes

A hydrocarbon...

Question

A hydrocarbon with molecular formula $C_{6} H_{12}$ has four isomeric alkenes $A - D$ and all on hydrogenation yield the same methyl cyclopentane Also $C$ is the only one that can be resolved into enantiomers The heat of hydrogenation of $A, B$ and $D$ are in the order of $B < D < A$ . The heat liberated in the hydrogenation reaction. Identify $A$ to $D$ .

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Solution

The isomers of methyl cyclopentane one which can be resolved in enantiomer is
Hence it is C,
The remaining are based on stability, more stable $\propto$ more hydrogenation energy.

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Similar questions

Five isomeric alkenes (all positional isomers)

A

E

, all on catalytic hydrogenation with

H_{2} / P t

gives the same optically active alkane

F

. Only A and B are optically active and

A

liberate more heat on hydrogenation than

B . C

show geometrical isomerism.

E

evolves more heat on hydrogenation than

D

.

Alkene liberating least heat on hydrogenation is:

Q. Three different isomeric alkenes

A, B

C

has molecular formula

C_{5} H_{10}

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A < B < C .

Deduce structures of

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C

Q. A hydrocarbon has molecular formula

C_{6} H_{8}

and it can be resolved into enantiomers However, catalytic hydrogenation of the above hyhdrocarbon gives 3-methyl pentane.Deduce structure of hydrocarbon.

Q. An organic compound has molecular formula A

(C_{7} H_{10})

and known to decolourized

B r_{2}

-water solution.A on reduction with

H_{2} / P t

(C_{7} H_{14})

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C_{7} H_{13} C l

. A on ozonolysis followed by work-up with Zn-dimethyl sulphide affords two and only two products, one being methanal and other C

(C_{6} H_{8} O_{3})

. C is oxidised with acidic solution of dochromate to yields D

(C_{6} H_{8} O_{5})

which is soluble in

N a H C O_{3}

. D is reduced with

N a B H_{4}

(C_{6} H_{10} O_{3})

which may be resolved into enantiomers. Identify A to E.

Q. An organic compound

X (C_{5} H_{8} O_{2})

C O_{2}

on treatment with

N a H C O_{3}

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Y (C_{5} H_{10} O_{2})

which can be resolved into enantiomers. The correct deduction is /are :

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