Exam 17: Carbonyl Alpha-Substitution and Condensation Reactions

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Consider the structures below to answer the following question(s). Consider the structures below to answer the following question(s).   -Refer to instructions. Underline the most acidic hydrogen atoms in each of the molecules. -Refer to instructions. Underline the most acidic hydrogen atoms in each of the molecules.

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Give the major organic product(s) of each reaction or sequences of reactions for the following question(s). Show all relevant stereochemistry. -Refer to instructions. a)Give major product(s): Give the major organic product(s) of each reaction or sequences of reactions for the following question(s). Show all relevant stereochemistry. -Refer to instructions. a)Give major product(s):   b)Why are two equivalents of Na<sup>+</sup> OEt− required? b)Why are two equivalents of Na+ OEt− required?

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a) a)   b)The second equivalent is needed for the second intramolecular alkylation step that produces the ring. b)The second equivalent is needed for the second intramolecular alkylation step that produces the ring.

Draw the structures of the precursors to the Michael reaction products shown in the question(s) below. Label the Michael donor and the Michael acceptor in each case and formulate the reaction. -Draw and label: Draw the structures of the precursors to the Michael reaction products shown in the question(s) below. Label the Michael donor and the Michael acceptor in each case and formulate the reaction. -Draw and label:

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Which of the following does not possess an enol form? Explain your choice. Which of the following does not possess an enol form? Explain your choice.

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Consider the reaction below to answer the following question(s). Consider the reaction below to answer the following question(s).   -Refer to instructions. Write the complete stepwise mechanism for the reaction above. Show all intermediate structures and all electron flow with arrows. -Refer to instructions. Write the complete stepwise mechanism for the reaction above. Show all intermediate structures and all electron flow with arrows.

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Which of the following would form an enolate ion on treatment with a base? Which of the following would form an enolate ion on treatment with a base?

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Consider the reaction below to answer the following question(s). Consider the reaction below to answer the following question(s).   -Refer to instructions. Which carbonyl compound functions as the electrophile in this reaction? -Refer to instructions. Which carbonyl compound functions as the electrophile in this reaction?

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Which of the following is common to both tautomers and resonance forms of a compound?

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Identify the intermediate imine that results from the following reaction. Identify the intermediate imine that results from the following reaction.

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Consider the structures below to answer the following question(s). Consider the structures below to answer the following question(s).   -Refer to instructions. Rank the molecules above in order of increasing acidity (least acidic to most acidic). -Refer to instructions. Rank the molecules above in order of increasing acidity (least acidic to most acidic).

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Refer to the compounds below to answer the following question(s). Refer to the compounds below to answer the following question(s).   -Refer to instructions. Underline all the acidic hydrogen atoms in Compounds I through IV. -Refer to instructions. Underline all the acidic hydrogen atoms in Compounds I through IV.

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Give the major organic product(s) of each reaction or sequences of reactions for the following question(s). Show all relevant stereochemistry. -Give major product(s): Give the major organic product(s) of each reaction or sequences of reactions for the following question(s). Show all relevant stereochemistry. -Give major product(s):

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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: 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:

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Consider the reaction sequence below to answer the following question(s). Consider the reaction sequence below to answer the following question(s).   -Refer to instructions. Conversion of A into B is a type of reaction termed _____. -Refer to instructions. Conversion of A into B is a type of reaction termed _____.

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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: 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:

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Refer to the compounds below to answer the following question(s). Refer to the compounds below to answer the following question(s).   -Refer to instructions. Draw the structure for the enol and enolate ions corresponding to Compound I. -Refer to instructions. Draw the structure for the enol and enolate ions corresponding to Compound I.

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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: 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:

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Consider the reaction below to answer the following question(s). Consider the reaction below to answer the following question(s).   -Refer to instructions. This reaction is an example of: -Refer to instructions. This reaction is an example of:

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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: 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:

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Predict the major aldol product of the following reaction. Predict the major aldol product of the following reaction.

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