Concept explainers
a)
Interpretation:
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are to be given.
Concept introduction:
Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β-diketones or β-ketonitriles or malonic esters (donors) to an unhindered α,β-unsaturated
To give:
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown.
Answer to Problem 62AP
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are
Explanation of Solution
An analysis of the structure of the compound indicates that it is formed by the reaction between the ethylacetoacetate (nucleophilic donor) and phenyl vinyl ketone (electrophilic acceptor).
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are
b)
Interpretation:
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are to be given.
Concept introduction:
Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β-diketones or β-ketonitriles or malonic esters (donors) to an unhindered α,β-unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β-carbon of the unsaturated ester.
To give:
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown.
Answer to Problem 62AP
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are
Explanation of Solution
An analysis of the structure of the compound indicates that it is formed by the reaction between the ethylacetoacetate (nucleophilic donor) and methyl vinyl ketone (electrophilic acceptor).
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are
c)
Interpretation:
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are to be given.
Concept introduction:
Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β-diketones or β-ketonitriles or malonic esters (donors) to an unhindered α,β-unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β-carbon of the unsaturated ester.
To give:
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown.
Answer to Problem 62AP
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are
Explanation of Solution
An analysis of the structure of the compound indicates that it is formed by the reaction between the ethylacetoacetate (nucleophilic donor) and vinyl nitrile (electrophilic acceptor).
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are
d)
Interpretation:
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are to be given.
Concept introduction:
Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β-diketones or β-ketonitriles or malonic esters (donors) to an unhindered α,β-unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β-carbon of the unsaturated ester.
To give:
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown.
Answer to Problem 62AP
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are
Explanation of Solution
An analysis of the structure of the compound indicates that it is formed by the reaction between nitro ethane (nucleophilic donor) and ethylacrylate (electrophilic acceptor).
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are
e)
Interpretation:
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound are to be given.
Concept introduction:
Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β-diketones or β-ketonitriles or malonic esters (donors) to an unhindered α,β-unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β-carbon of the unsaturated ester.
To give:
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown.
Answer to Problem 62AP
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are
Explanation of Solution
An analysis of the structure of the compound indicates that it is formed by the reaction between the ethylsuccinate (nucleophilic donor) and nitro ethene (electrophilic acceptor).
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are
f)
Interpretation:
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are to be given.
Concept introduction:
Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β-diketones or β-ketonitriles or malonic esters (donors) to an unhindered α,β-unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β-carbon of the unsaturated ester.
To give:
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown.
Answer to Problem 62AP
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are
Explanation of Solution
An analysis of the structure of the compound indicates that it is formed by the reaction between nitro methane (nucleophilic donor) and 2-cyclopentenone (electrophilic acceptor).
The nucleophilic donor and electrophilic acceptor that react in a Michael reaction to yield the compound shown are
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Chapter 23 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
- Predict the major organic product(s) of the following reactions. Include stereochemistry when necessary. Write NR if no reaction, try to explain.arrow_forwardQ2: Explain why epoxides that react in an SN1 manner will not show any stereochemical inversion in the product. Q3: Rationalize why Alcohol B will react under the indicated reaction conditions, but Alcohol A will not. A ☑ OH B OH PBr3 R-Brarrow_forwardQ1: Predict the major organic product(s) of the following reactions. Include stereochemistry when necessary. Write NR if no reaction, try to explain. 1.) LDA, THF 2.) СОН CI OH H2SO4, heat OH m...... OH 1.) PCC, CH2Cl2 2.) CH3CH2MgBr, THF 3.) H3O+ 4.) TsCl, pyr 5.) tBuOK, tBuOH 1.) SOCI 2, CHCI 3 2.) CH3CH2ONA, DMF OH 1.) HBr 2.) Mg, THF 3.) H₂CO, THE 4.) H3O+ OH NaH, THFarrow_forward
- Problem 6-29 Identify the functional groups in the following molecules, and show the polarity of each: (a) CH3CH2C=N CH, CH, COCH (c) CH3CCH2COCH3 NH2 (e) OCH3 (b) (d) O Problem 6-30 Identify the following reactions as additions, eliminations, substitutions, or rearrangements: (a) CH3CH2Br + NaCN CH3CH2CN ( + NaBr) Acid -OH (+ H2O) catalyst (b) + (c) Heat NO2 Light + 02N-NO2 (+ HNO2) (d)arrow_forwardPredict the organic product of Y that is formed in the reaction below, and draw the skeletal ("line") structures of the missing organic product. Please include all steps & drawings & explanations.arrow_forwardPlease choose the best reagents to complete the following reactionarrow_forward
- Problem 6-17 Look at the following energy diagram: Energy Reaction progress (a) Is AG for the reaction positive or negative? Label it on the diagram. (b) How many steps are involved in the reaction? (c) How many transition states are there? Label them on the diagram. Problem 6-19 What is the difference between a transition state and an intermediate? Problem 6-21 Draw an energy diagram for a two-step reaction with Keq > 1. Label the overall AG°, transition states, and intermediate. Is AG° positive or negative? Problem 6-23 Draw an energy diagram for a reaction with Keq = 1. What is the value of AG° in this reaction?arrow_forwardProblem 6-37 Draw the different monochlorinated constitutional isomers you would obtain by the radical chlorination of the following compounds. (b) (c) Problem 6-39 Show the structure of the carbocation that would result when each of the following alkenes reacts with an acid, H+. (a) (b) (c)arrow_forwardPlease draw the major product of this reaction. Ignore inorganic byproducts and the carboxylic side productarrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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