We discussed a tetrahedral intermediate in the context of reactions of derivatives of carboxylic acids and nucleophilic substitution reactions. In all of these cases, the tetrahedral intermediate was described as an unstable structure that undergoes subsequent reactions. Briefly explain why tetrahedral intermediates are unstable.

We discussed a tetrahedral intermediate in the context of reactions of derivatives of carboxylic acids and nucleophilic substitution reactions. In all of these cases, the tetrahedral intermediate was described as an unstable structure that undergoes subsequent reactions. Briefly explain why tetrahedral intermediates are unstable.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

See similar textbooks

Similar questions

Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.
Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.
Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)
Substitutions on aromatic rings are generally carried out by electrophilic substitution, but for the synthesis of phenolic compounds and alkoxy benzene it is carried out by nucleophilic substitution, explain why this is so .
Describe a sequence of reactions for the following reaction
The following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.
Write the mechanism, as well as the structure of intermediate A and product B, for the following reaction.
b) Esters can undergo hydrolysis to give an alcohol and a carboxylic acid. Lactone P which is a cyclic ester, can undergo base-catalyzed hydrolysis to give a hydroxy carboxylic acid. Write the plausible mechanism for the transformation.
Propanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4. The reaction of propanal proceeds with acidified potassium cyanide proceeds more rapidly than that of propanone. Referring to the mechanism of the reactions, explain this phenomenon.
Define central relationship between nucleophilicity and basicity in comparing two nucleophiles?
The odor of ripe bananas and many other fruits is due to the presence of esters. For example: Banana oil (isopentyl acetate) (a) Write the name (common or IUPAC) of the ester responsible for the fragrance of the following: pineapple, orange, apple, peach, & lavender (b) Choose one fragrant from (a) and name the alcohol and the carboxylic acid needed to synthesize this ester. (c) Show the detailed mechanism of the Fischer Esterification reaction that will be involved in the synthesis of the fragrant you have chosen in part (a).
Provide a step-by-step mechanism for the reaction.