Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon See all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

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.