In the presence of an acid catalyst, acetaldehyde forms a trimer known as paraldehyde. Because it induces sleep when it is administered to animals in large doses, paraldehyde is used as a sedative or hypnotic. Propose a mechanism for the formation of paraldehyde.
Bruice 8th Edition
Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
Problem 90Identify compounds A and B:

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Key Concepts
Grignard Reagents
Organocuprates
Acid Workup
Shown below is the 1H NMR spectrum of the alkyl bromide used to make the phosphonium ylide that reacts with a ketone in a Wittig reaction to form a compound with molecular formula C11H14. What product is obtained from the Wittig reaction?
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The pKa values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98.
b. The amount of hydrate present in an aqueous solution of oxaloacetic acid depends on the pH of the solution: 95% at pH 0, 81% at pH 1.3, 35% at pH 3.1, 13% at pH 4.7, 6% at pH 6.7, and 6% at pH 12.7. Explain this pH dependence.
What carbonyl compound and what phosphonium ylide are needed to synthesize the following compounds?
b.
Show how each of the following compounds can be prepared from the given starting material. In each case, you will need to use a protecting group.
a.
b.
When a cyclic ketone reacts with diazomethane, the next larger cyclic ketone is formed. This is called a ring-expansion reaction. Draw a mechanism for the following ring-expansion reaction.