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Exam 16: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

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Question 21

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

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Question 22

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Of the following,which represents a possible direct conversion of the reactant to product shown?

A) ester to acid chloride
B) thioester to acid anhydride
C) ester to amide
D) acid anhydride to acid chloride

E) C) and D)
F) B) and C)

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Question 23

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Instructions: Provide the missing structure(s)or reagent(s)for each reaction or sequences of reactions.Show all relevant stereochemistry. -Provide missing structure(s):

Draw the major product of the following reaction.

Instructions: Provide the missing structure(s)or reagent(s)for each reaction or sequences of reactions.Show all relevant stereochemistry. -Provide missing structure(s):

The following a monomer of the polymer used in biodegradable sutures called Lactomerâ.Upon hydrolysis what product(s)form(s)? Draw the appropriate structure(s).

Instructions: Provide the missing structure(s)or reagent(s)for each reaction or sequences of reactions.Show all relevant stereochemistry. -Provide missing structure(s):

Which of the following is the correct assignment of the classes of the following compounds?

Which of the following compounds is a 2 ^$\circ$ amide?

What is the major organic product produced by the following reaction?

Which of the following best describes the key mechanistic steps in the reaction of an acid chloride and an alcohol to form an ester?

Instructions: Tell which spectroscopic technique you would use to distinguish between the two members of the pair.Tell what differences you would expect to see. -Identify spectroscopic technique:

Rank the following from highest to lowest reactivity toward reaction with EtOH.

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

Draw the major product of the following reaction (which affords a penicillin derivative).

Instructions: Consider the reaction below to answer the following question(s) . -Refer to instructions.The purpose of the base catalyst in this reaction is:

Instructions: Consider the information below to answer the following question(s) . The reaction of a carboxylic acid with an alcohol in the presence of acid is termed a Fischer esterification. -Refer to instructions.The nucleophile in this reaction is indicated by letter _____.

The two spectra below belong to acetic acid (ethanoic acid)and its isomer,methyl formate (methyl methanoate).Which spectrum corresponds to which compound? Explain your answer. (Spectra obtained from SDBSWeb:http://www.aist.go.jp/RIODB/SDBS)

Instructions: Consider the information below to answer the following question(s) . The reaction of a carboxylic acid with an alcohol in the presence of acid is termed a Fischer esterification. -Refer to instructions.Compound C functions as _____ in this reaction.

Instructions: Consider the information below to answer the following question(s). The reaction of a carboxylic acid with an alcohol in the presence of acid is termed a Fischer esterification. -Refer to instructions.What would be the identity of A,B and C needed to produce the following compound?