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Which of the following reagents can be used to convert 1-pentyne into an aldehyde?Select answer from the options belowNaOH1. 9-BBN  2. NaOH, H2O2      H2SO4, H2O, HgSO4

Question

Which of the following reagents can be used to convert 1-pentyne into an aldehyde?Select answer from the options belowNaOH1. 9-BBN  2. NaOH, H2O2      H2SO4, H2O, HgSO4

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Solution

The reagent that can be used to convert 1-pentyne into an aldehyde is 1. 9-BBN 2. NaOH, H2O2.

Here's the step-by-step process:

  1. 9-BBN (9-Borabicyclo[3.3.1]nonane) is used for hydroboration, which adds a BH2 group to the less substituted carbon of the alkyne. This results in a vinyl borane intermediate.

  2. The vinyl borane is then oxidized using NaOH and H2O2 (hydrogen peroxide) in a process called oxidation. This step replaces the BH2 group with a hydroxyl group (OH), resulting in an enol.

  3. The enol then spontaneously tautomerizes to the more stable carbonyl form, which in this case is an aldehyde.

The other reagent, H2SO4, H2O, HgSO4, would add water across the triple bond of the alkyne in a Markovnikov manner, resulting in a ketone, not an aldehyde.

This problem has been solved

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