Organic Chemistry Practice Problems Alpha-Carbon Racemization Practice Problems Solution: Read the following statement and fill in the blank...

Solution: Read the following statement and fill in the blanks with A, B or C. As a reference the image below represents what is occuring. There are 4 empty spaces meaning an answer may be used more than once.  A. chiral         B. achiral         C. racemic   We know that a carbonyl can react with either acid or base to form an enol. However, it gets interesting when there are substituents at the alpha position. If we start out with a            carbonyl and react through either an acid-catalyzed or base-catalyzed mechanism, we form an identical enol in both cases through different intermediates. The base-catalyzed mechanism forms an enolate anion, while the alpha does not. The enol that we form however, changes and becomes            . This means that when we react through acid or base-catalyzed mechanisms and go through an enol we will form a          mixture if our starting material is            and contains an alpha hydrogen at that position.   

Problem

Read the following statement and fill in the blanks with A, B or C. As a reference the image below represents what is occuring. There are 4 empty spaces meaning an answer may be used more than once. 

A. chiral         B. achiral         C. racemic

 

We know that a carbonyl can react with either acid or base to form an enol. However, it gets interesting when there are substituents at the alpha position. If we start out with a            carbonyl and react through either an acid-catalyzed or base-catalyzed mechanism, we form an identical enol in both cases through different intermediates. The base-catalyzed mechanism forms an enolate anion, while the alpha does not. The enol that we form however, changes and becomes            . This means that when we react through acid or base-catalyzed mechanisms and go through an enol we will form a          mixture if our starting material is            and contains an alpha hydrogen at that position. 

 

Additional Practice Problems

Alpha-Carbon Racemization

Alpha-Carbon Racemization

Q. Which of the following would undergo racemization in base?

Solved • Tue Apr 05 2016 12:20:04 GMT-0400 (EDT)