(a)
Interpretation: The product of given two-step sequence is to be drawn.
Concept introduction: The replacement or substitution of one
(b)
Interpretation: The product of given two-step sequence is to be drawn.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.
(c)
Interpretation: The product of given two-step sequence is to be drawn.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.
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- b) Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. OMe HO + OMe + OH HO + CH; OHarrow_forwardAcyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. CI H₂N OH • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • Do not include counter-ions, e.g., Na+, I, in your answer. • In cases where there is more than one answer, just draw one. Sn [Farrow_forward10. Why do aldehydes undergo nucleophilic addition reactions (rxns from Unit 10) while esters undergo nucleophilic acyl substitution (rxns from Unit 11) reactions? A) The carbonyl carbon of an ester is more electrophilic than that of an aldehyde. B) Aldehydes are more sterically hindered than esters. C) Once the nucleophile adds to an aldehyde, the tetrahedral intermediate is too sterically hindered to eliminate one of the attached groups. D) The ester carbonyl carbon is sp3 hybridized while the aldehyde carbonyl carbon is sp2 hybridized. E) Once the nucleophile adds to an aldehyde, neither H- nor R- can be eliminated since they are strongly basic.arrow_forward
- Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. You do not have to consider stereochemistry. Include all valence lone pairs in your answer. Do not include counter-ions, e.g., Na+, I-, in your answer. In cases where there is more than one answer, just draw one.arrow_forwardAcyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. You do not have to consider stereochemistry. Include all valence lone pairs in your answer. Do not include counter-ions, e.g., Na+, I-, in your answer. In cases where there is more than one answer, just draw one.arrow_forwardDetermine whether the following reaction is an example of a nucleophilic substitution reaction: O" Molecule A + NO₂ Molecule B NO₂ + Harrow_forward
- Draw curved arrows to show the movement of electrons in this step of the mechanism.arrow_forwardThe question is: "Draw the curved arrow mechanism for the reaction between pentan-2-one and (CH3)3O– in t-butanol to form an enolate. Draw all electrons and charges on both resonance structures. Then answer the question about the reaction." I got the initial arrows correct, but am not entirely sure what the carbanion intermediate would look like and then what the curved arrows would be to convert it to its final oxanion formarrow_forwardDraw the structure of the product of the Michael reaction between propenamide and diethyl malonatearrow_forward
- Write equations and answer questions for the following: Step 1: conversion of 1-bromobutane into a Grignard reagent. o Step 2: reaction of the Grignard reagent with the ketone to form an alkoxide salt. Identify the nucleophile (and its nucleophilic site) and electrophile (and its electrophilic site) in this reaction. O Step 3: protonation of the alkoxide salt using ammonium chloride as the proton source. Identify the acid and base in this reaction. o Write the net reaction.arrow_forwardThis reaction does not follow the expected theory. Given what you know about substitution/elimination, what is the expected mechanism this reaction should follow? Suggest why that is not what happens and give the actual product of the reaction. Br ткон sarrow_forwardRank the following esters from most reactive to least reactive in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate): Rank the same esters from most reactive to least reactive in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning