The addition of HBr to propene yields 2-broniopropane, while in
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An alkene ‘A’ contains three C-C eight C-H bonds, one C - C straight pi bond. ‘A’ on ozonolysis gives two moles of an aldehyde of molar mass 44 amu. Write the IUPAC name of ‘A’. 


(i) An aldehyde having molar mass 44 amu is ethanal (CH3CHO).

(ii) Write two moles of ethanal side by side with their oxygen atoms facing towards each other.



(iii) Remove the oxygen atoms and join the two ends by a double bond. 



But-2-ene has three C-C, eight C-H and 

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An alkene 'A' on ozonolysis gives a mixture of ethanal and pentan-3-one.  Write structure and IUPAC name of 'A'.


(i) Write the structure of the products side by side with their oxygen atoms facing towards each other



(ii) Remove the oxygen atoms and join the two ends by a double bond. Thus the structure of the alkene A is



The above product we get as,

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Draw the cis and trans structures of hex-2-ene. Which isomer will have higher b.p. and why?


Hex-2-ene has the following cis and trans structures:



cis isomer possesses higher boiling point due to the greater magnitude of dipole-dipole interactions as compared to the trans isomer.


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Propanal and pentan-3-one are the ozonolysis products of an alkene? What is the structural formula of the alkene?


(i) Write the structures of propenal and pentan-3-one side by side with their oxygen atom facing towards each other.



(ii) Remove the oxygen atoms and join the two ends by a double bond. Thus the structure of the alkene is



 
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The addition of HBr to propene yields 2-broniopropane, while in the presence of benzoyl peroxide, the same reaction yields 1-bromopropane. Explain and give mechanism. 


Formation of 2-Bromopropane: Addition to HBr to propene is an ionic electrophilic addition reaction in which the electrophile, (H+) adds to form a more stable 2° carbocation. In the 2nd reaction, the carbocation is rapidly attacked by the nucleophile (Br-) to form 2-bromopropane.



Formation of 1-Bromopropane:
In the presence of benzoyl peroxide, the addition of HBr to propene involves free radical mechanism in which Br-free radical is obtained by the action of benzoyl peroxide on HBr.

(i) Br radical adds to propene to form the more stable 2° free radical.

(ii) Free radical thus obtained rapidly abstracts a hydrogen atom from HBr to form 1-bromopropane.




 


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