Q50 of 51 Page 170

An unsaturated hydrocarbon ‘A’ adds two molecules of H2 and on reductive ozonolysis gives butane-1,4-dial, ethanal and propanone. Give the structure of ‘A’, write its IUPAC name and explain the reactions involved.

‘A’ add two mole H2 so it has 2 double bond in the hydrocarbon chain.

On reductive ozonolysis of compound having double bond break the double bond and respective product after breaking double bond form either ketone or aldehyde .


A after reductive ozonolysis form following compound -


So compound A is



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47

In the following questions a statement of assertion (A) followed by a statement of reason (R) is given. Choose the correct option out of the choices given below each question.

Assertion (A) : Among isomeric pentanes, 2, 2-dimethylpentane has highest boiling point.


Reason (R) : Branching does not affect the boiling point.


(i) Both A and R are correct and R is the correct explanation of A.


(ii) Both A and R are correct but R is not the correct explanation of A.


(iii) Both A and R are not correct.


(iv) A is not correct but R is correct.


48

An alkyl halide C5H11Br (A) reacts with ethanolic KOH to give an alkene ‘B’, which reacts with Br2 to give a compound ‘C’, which on dehydrobromination gives an alkyne ‘D’. On treatment with sodium metal in liquid ammonia one mole of ‘D’ gives one mole of the sodium salt of ‘D’ and half a mole of hydrogen gas. Complete hydrogenation of ‘D’ yields a straight chain alkane. Identify A,B, C and D. Give the reactions involved.

49

896 mL vapour of a hydrocarbon ‘A’ having carbon 87.80% and hydrogen 12.19% weighs 3.28g at STP. Hydrogenation of ‘A’ gives 2-methylpentane. Also ‘A’ on hydration in the presence of H2SO4 and HgSO4 gives a ketone ‘B’ having molecular formula C6H12O. The ketone ‘B’ gives a positive iodoform test. Find the structure of ‘A’ and give the reactions involved.

51

In the presence of peroxide addition of HBr to propene takes place according to anti Markovnikov’s rule but peroxide effect is not seen in the case of HCl and HI. Explain.