You visited us 2 times! Enjoying our articles? Unlock Full Access!

Byju's Answer

Standard XII

Chemistry

Physical Properties of Alkenes

An organic co...

Question

An organic compound has molecular formula A $(C_{7} H_{10})$ and known to decolourized $B r_{2}$ -water solution.A on reduction with $H_{2} / P t$ produces B $(C_{7} H_{14})$ . B on monochlorination with $C l_{2} / h v$ produces four isomeric monochloro derivatives $C_{7} H_{13} C l$ . 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 $N a B H_{4}$ to yield E $(C_{6} H_{10} O_{3})$ which may be resolved into enantiomers. Identify A to E.

Open in App

Solution

Step 1- $A$ has multiple bond as it gives the unsaturation test with $B r_{2}$ water
Step 2- Ozonolysis of $A$ in the presence of $Z n - M e_{2} S$ (Stops the oxidation upto aldehyde) will result in $C$
Step 3- Oxidation with strong oxidising agent $K_{2} C r_{2} O_{7}$ will results in compound $D$ , that will oxidise the aldehyde part to $C O O H$
Step 4- $N a B H_{4}$ can't reduce the $C O O H$ so it will reduce the ketone part and convert it to alcohol.

Suggest Corrections

Similar questions

Q. A hydrocarbon

A

(C_{5} H_{10})

on addition of

H B r

in presence of a peroxide forms

(C_{5} H_{11} B r)

B

which is found to be resolvable into enantiomers.

A

on addition of

H B r

in aqueous medium produces

C

which is an isomer of

B

but can't be resolved.

A

on reductive ozonolysis produced

(C_{4} H_{8} O)

D

as one product.

D

on catalytic reduction with

N a B H_{4}

produced E

(C_{4} H_{10} O)

which is resolvable.

E

on dehydration with concentrated sulphuric acid produced

F

(C_{4} H_{8})

which on ozonolysis followed by work-up with

Z n - H_{2} O

produced two molecules of ethanol. Identify

A

F

Q. An organic compound

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

reacts with

B r_{2}

in presence of phosphorus to produce

B

which can be resolved into enantiomers.

B

on dehydrobromination yields

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

which does not show stereoisomerism.

C

on decarboxylation gives an alkene which on further ozonolysis gives

D

and

E

D

gives Schiff's test but

E

does not. The correct identity of these compounds are:

Q. An organic compound contains C, H and O, and its aqueous solution is neutral. 1.44 g of A on refluxing with dilute

H_{2} S O_{4}

produces two organic compounds B and C of which the only B is resolvable and gives effervescence with

N a H C O_{3}

. Also, neutralization of entire B requires 0.4 g of

N a O H

. B on reduction with HI/red phosphorus produces a hydrocarbon D which is non-resolvable. Also D on monochlorination yield three alkyl halide in which the only one is resolvable. Deduce structures of A to D.

Q. An organic acid

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

reacts with

B r_{2}

in presence of phosphorus to produce a resolvable compound B. B on dehydrobromination yields C. C does not show geometrical isomerism and on decarboxylation gives an alkene D. D on ozonolysis gives E and F. Compound E gives positive Schiff's test but F does not. Give structures of A to F.

Q. An organic compound A has molecular formula

C_{6} H_{10} O_{2} .

A on heating with

N a O H / C a O

yields Compound

B (C_{5} H_{10})

B on treatment with

C l_{2}

in presence of UV- light yields a single isomer of monochloro compound C (

C_{5} H_{9} C l

Identify compounds A to C.

Join BYJU'S Learning Program