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Hydrohalogenation of Alkenes

Which of the ...

Question

Which of the following works best as the reaction step to carry out the conversion?

(i)

B r_{2}

(ii)

N a N H_{2}

(excess)

(iii)

H_{2} O, H g S O_{4} / H_{2} S O_{4}

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(i)

B_{2} H_{6}

/diglyme

(ii)

H_{2} O_{2}, N a O H

(iii)

P C C / C H_{2} - C l_{2}

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(i)

H_{2} O, H_{2} S O_{4}

(ii)

C r O_{3} / H_{2} S O_{4}

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(i)

C H_{3} O | | C O O H

(ii)

N a O H, H_{2} O

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Solution

The correct option is B (i) $B_{2} H_{6}$ /diglyme
(ii) $H_{2} O_{2}, N a O H$
(iii) $P C C / C H_{2} - C l_{2}$

Hydroboration reaction of alkene results in the formation of alcohol by anti-Markovnikov's rule. Then PCC (Pyridinium Chlorochromate) oxidizes primary alcohols to aldehydes and secondary alcohols to ketones.
Other reagents result in Markovnikov's addition into alcohol which oxidize it further to the ketone.

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