2/19/2017 11:55 PM A 43/50 O 2/17/2017 09:40 AM 68 Gradebook Print calculator Pe

Question

2/19/2017 11:55 PM A 43/50 O 2/17/2017 09:40 AM 68 Gradebook Print calculator Periodic Table Question 23 of 32 Map A Organic Chemistry Roberts & Company Publishers Loudon presented by Sapling Learning For each of the following alcohols, which method of synthesis, (a) hydroboration-oxidation or (b) oxymercuration-reduction, can produce the alcohol relatively free of constitutional isomers and diastereomers? (Drag an alcohol to the appropriate bin if it can be made by that method.) (a) hydroboration-oxidation (b) oxymercuration-reduction OH OH CH3CH2 CH-CH2CH2CH3 A O Previous Check Answer Next d Exit Hint

Explanation / Answer

1) hydroboration -oxidation reaction:

in this reaction CnH2n convert into CnH2n+1OH by water molecule addition to CnH2n.

In your options 3 are of cyclopentene & 1 is n-hexane.

Hydroboration leads to stereo chemistry & in this OH & H radicals are add into opposite of double bond.

Here, I react first cyclopentene with alkyl radical group.

OH is not there initially so that option 2 isn't possible.

If I react this with hydrogen + boron contain compound than...

In this mechanism OH attract with carbon with less number of hydrogen atom.

So, 4th option is correct.

2)oxymercuration-reduction reaction:

Oxymercuration ,name itself suggests that oxygen & mercury contain compound are added to alkene across double bond of alkene molecule.

Reduction means addition of hydrogen atom by removing of boron contain compounds.in this type of reaction OH group always attract towards more carbons.

So,options 3&4 aren't possible.

Because hydrogen is there on more carbon position & also this type of reactions are leads to stereo chemistry.so,option 1 isn't possible.

So,option 2 is right choice.

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