Q53d - Organic Chemistry (Mcmurry)

Question

Question: In planning the synthesis of one compound from another, it’s just as important to know what not to do as to know what to do. The following reactions all have serious drawbacks to them. Explain the potential problems of each.

Step-by-Step Solution

Answer

Answer

 

Wrong product is shown.

Step 1: Anti-markovnikov’s rule

In hydroboration-oxidation reaction proceeds in an Anti-Markovnikov manner, where hydrogen (from $B{H}_3$) attaches to the more substituted carbon. This reaction involves hydrogenation and electrophilic addition and it is syn addition, meaning that the hydroboration takes place on the same face of the double bond.

Step 2: Problem with reaction

The problem with the equation is that it is showing the wrong product. The actual product will have hydrogen and hydroxyl groups in the same phase.