Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 11, Problem 11.35P
Interpretation Introduction
Interpretation: A stepwise mechanism for the acid-catalyzed conversion of enamine X to imine Y is to be drawn.
Concept Introduction: The
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The Stork reaction is a condensation reaction between an enamine donor and an a,ß-unsaturated carbonyl acceptor. The overall reaction consists of a
three-step sequence of
1. formation of an enamine from a ketone,
2. Michael addition to an a,ß-unsaturated carbonyl compound, and
3. hydrolysis of the enamine in dilute acid to regenerate the ketone.
Consider the Stork reaction between acetophenone and propenal.
1 Draw the structure of the product of the enamine formed between acetophenone and morpholine.
90-85
?
What is the major Hofmann elimination product formed from each amine?
Write the mechanism for the following reactions:
1. the acid-catalyzed hydrolysis of an imine to a carbonyl compound and a primary amine
2. the acid-catalyzed hydrolysis of an enamine to a carbonyl compound and a secondary amine a. How do the two mechanisms differ?
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Draw structures for the three alkynes having...Ch. 11 - Prob. 11.2PCh. 11 - Give the IUPAC name for each compound.Ch. 11 - Give the structures corresponding to each of the...Ch. 11 - Prob. 11.5PCh. 11 - Prob. 11.6PCh. 11 - Which bases can deprotonate acetylene? The pKa...Ch. 11 - Draw the organic products formed when each alkyne...Ch. 11 - Prob. 11.9PCh. 11 - Problem 11.9 Draw the products formed when is...
Ch. 11 - Explain the following result. Although alkenes...Ch. 11 - Problem 11.11 Draw the keto tautomer of each...Ch. 11 - Prob. 11.13PCh. 11 - a Draw two different enol tautomers of...Ch. 11 - Prob. 11.15PCh. 11 - Prob. 11.16PCh. 11 - Prob. 11.17PCh. 11 - Problem. 11.17 Show how , and can be used to...Ch. 11 - Prob. 11.19PCh. 11 - Draw the products of each reaction. a. b.Ch. 11 - Prob. 11.21PCh. 11 - Problem 11.21 Use retrosynthetic analysis to show...Ch. 11 - Prob. 11.23PCh. 11 - Give the IUPAC name for each compound. a. b.Ch. 11 - Prob. 11.25PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - Prob. 11.27PCh. 11 - Give the IUPAC name for each alkyne.Ch. 11 - Prob. 11.29PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 11.31PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 11.33PCh. 11 - Prob. 11.34PCh. 11 - Prob. 11.35PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - Draw the products formed when 3-hexyne is treated...Ch. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - What alkynes give each of the following ketones as...Ch. 11 - Prob. 11.41PCh. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - Prob. 11.43PCh. 11 - Draw the structure of compounds A-E in the...Ch. 11 - Prob. 11.45PCh. 11 - Prob. 11.46PCh. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - 11.45 Explain the following statement. Although ...Ch. 11 - Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.52PCh. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - Prob. 11.55PCh. 11 - Synthesize each compound from acetylene. You may...Ch. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - 11.55 Devise a synthesis of the ketone, , from ...Ch. 11 - 11.56 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.61PCh. 11 - Prob. 11.62PCh. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.65PCh. 11 - Write a stepwise mechanism for each of the...Ch. 11 - Prob. 11.67PCh. 11 - 11.65 Explain why an optically active solution of ...
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- 18) The following reaction undergoes three distinct steps: imine formation, electrophilic aromatic substitution, and decarboxylation. Draw each of the intermediates from each of these three steps as well as the final product. BS NH₂ OH heatarrow_forwardRank the following esters in order of decreasing reactivity in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate):Rank the same esters in order of decreasing reactivity in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).arrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an a,ẞ-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of 1. formation of an enamine from a ketone. 2. Michael addition to an α,ß-unsaturated carbonyl compound, and 3. hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between cyclohexanone and propenal. Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. ચર્ચ F Correct HC, CH3 ChemDoodle 2 Draw the structure of the Michael addition product. ChemDoodle Jn (F 106 Correctarrow_forward
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