Organic Chemistry : Help with Other Carbonyl Products

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #631 : Organic Chemistry

When butanoic acid undergoes the Hell-Volhard-Zelinsky (HVZ) reaction, the final product is __________.

Possible Answers:

heptanoic acid

None of the other answers

butanoyl bromide

3-bromobutanoic acid

2-bromobutanoic acid

Correct answer:

2-bromobutanoic acid

Explanation:

In the HVZ reaction of a carboxylic acid, a bromine is added to the alpha carbon. Phosphorus catalyzes the reaction and allows for the formation of an acyl halide. Acyl halides readily undergo enol-ketone tautomerization. The enol form uses electrons from the carbon-carbon double bond to bond to the bromine. In water, the two bromine molecules convert back to a carboxylic acid with one bromine on the alpha carbon.

Example Question #1 : Help With Other Carbonyl Products

Noname01

What is the product of the given reaction?

Possible Answers:

Noname01

Noname01

Noname02

Noname03

Noname02

Correct answer:

Noname01

Explanation:

This question tests knowledge on carboxylic acid derivatives and the formation of the carboxylic acid derivatives. , or thionyl chloride, reacts with a carboxylic acid to form an acid chloride. The choice that replaces the  with a . The reaction also expels .

Example Question #2 : Help With Other Carbonyl Products

Which combination of starting material and reagent will produce the product shown?

Screen shot 2015 11 15 at 11.19.43 am

Possible Answers:

5-hydroxyvaleric acid and 

5-hydroxyvaleric acid and 

4-hydroxybutyric acid and 

Pentanedioic acid and 

4-hydroxybutyric acid and 

Correct answer:

5-hydroxyvaleric acid and 

Explanation:

5-hydroxyvaleric acid (5-hydroxypentanoic acid) is a five-carbon carboxylic acid alcohol and will produce the required lactone. This reaction is typically acid-catalyzed. Pentanedioic acid (glutaric acid) is a linear dicarboxylic acid, 4-hydroxybutyric acid only has four carbons and will not produce the desired product without being modified.

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