Synthesis of Aldehydes or Ketones from Hydrocarbons
Consider the ...
Question
Consider the reaction. CH3−CH=CH2(i)BH3/THF−−−−−−−−−→(ii)H2O2/OH−APCC−−−−−−−→(inCH2Cl2)B CH3−CH=CH2+H2OH2SO4−−−−→CPCC−−−−−−−→(inCH2Cl2)D Identify the relation between B and D.
A
Functional isomers
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B
Positional isomers
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C
Chain isomers
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D
Metamers
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Solution
The correct option is A
Functional isomers The reagents BH3,THF followed by NaOH,H2O2 are hydroxylating agents. This reaction is called hydroboration-oxidation reatction. Alkenes undergo oxidation and anti-markovnikov's alcohol is the end product.
Alkenes react with water in the presence of a mineral acid as a catalyst to form alcohols. The H+ ion from the acid helps to form a carbocation for nucleophilic attack.
PCC(Pyridinium chlorochromate) is a mild oxidizing agent. It converts 1o alcohols to aldehydes and 2o alcohols to ketones, but is not strong enough to convert primary alcohols to carboxylic acids. CH3−CH=CH2(i)BH3/THF−−−−−−−−−→(ii)H2O2/OH−CH3−CH2−CH2OHPCC−−−−−−−→(inCH2Cl2)CH3−CH2−CHO CH3−CH=CH2+H2OH2SO4−−−−→CH3−CH(OH)−CH3PCC−−−−−−−→(inCH2Cl2)CH3−CO−CH3