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Chemistry
Study Set
Fundamentals of Organic Chemistry
Quiz 11: Carbonyl Alpha-Substitution Reactions and Condensation Reactions
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Question 1
Essay
Instructions: Draw the structure of the aldol self-condensation product of each compound for the following question(s). If a compound does not undergo aldol self-condensation, explain why it does not. Draw and explain:
Question 2
Essay
Instructions: Each of the following compounds in the following question(s) can be prepared by a mixed aldol condensation reaction. a) Give the structures of the aldehyde and/or ketone precursors for each aldol condensation product and formulate the reaction. b) Give the structure of the intermediate aldol product. Refer to instructions. Use the following compound:
Question 3
Essay
Instructions: Consider the reaction below to answer the following question(s).
Refer to instructions. Draw the structure of the enolate ion that is generated during the course of this reaction.
Question 4
Essay
Instructions: Consider the structures below to answer the following question(s).
Refer to instructions. Underline the acidic hydrogen atoms in each of the molecules.
Question 5
Essay
Instructions: Each of the following compounds in the following question(s) can be prepared by a mixed aldol condensation reaction. a) Give the structures of the aldehyde and/or ketone precursors for each aldol condensation product and formulate the reaction. b) Give the structure of the intermediate aldol product. Refer to instructions. Use the following compound:
Question 6
Short Answer
Which of the following does not possess an enol form? Explain your choice.
Question 7
Multiple Choice
Instructions: Consider the reaction below to answer the following question(s) .
Refer to instructions. This reaction is an example of:
Question 8
Essay
Instructions: Draw the structure of the aldol self-condensation product of each compound for the following question(s). If a compound does not undergo aldol self-condensation, explain why it does not. Draw and explain:
Question 9
Essay
Predict the major aldol product of the following reaction.
Question 10
Multiple Choice
Instructions: Consider the reaction below to answer the following question(s) .
Refer to instructions. The product of this reaction is:
Question 11
Short Answer
Rank the following hydrogens in terms of decreasing acidity (most acidic > least acidic):
Question 12
Short Answer
Instructions: Draw the structure of the product you would expect to obtain by Claisen condensation of the esters shown in the question(s) below. If an ester does not undergo Claisen condensation, explain why it does not. Draw and explain:
Question 13
Essay
Instructions: Draw the structure of the aldol self-condensation product of each compound for the following question(s). If a compound does not undergo aldol self-condensation, explain why it does not. Draw and explain:
Question 14
Short Answer
Instructions: Consider the reaction below to answer the following question(s).
Refer to instructions. Which carbonyl compound functions as the electrophile in this reaction?
Question 15
Essay
When treated with base and heat, the following diketone undergoes an intramolecular aldol reaction followed by dehydration to produce cis-jasmone, a perfume component. Draw the structure of the product.
Question 16
Essay
Identify products a and b.