Imine vs Enamine: Videos & Practice Problems

Provide the product of the reaction shown below.

Draw the product(s) of the reaction shown below, considering stereochemistry.

Identify the compound(s) which can form an imine with an aldehyde or a ketone.

Propose a suitable mechanism to show the imine formation in the given reaction.

Draw the structure of the imine given below.

• The (E) isomer of the methyl imine of acetophenone.

Propose a suitable mechanism to show the imine formation in the given reaction.

Draw the structure of the final product in the reaction given below.

Draw the major product expected from the reaction given below.

Show what amines and carbonyl compounds that produce the imines listed below.

Show what amines and carbonyl compounds that produce the imines listed below.

Draw a suitable mechanism for the acid-catalyzed hydrolysis of acetaldehyde methyl imine. The reaction is shown below.

Draw the structures of the major products expected from the reactions given below.

Draw the structures of the major products expected from the reactions given below.

Show the structures of the carbonyl compounds and amines that can give the imines given below.

Draw the structures of the major products expected from the reactions given below.

Determine the expected product of the acid-catalysed reaction between propiophenone and phenylmethanamine.

Determine the expected product of the acid-catalysed reaction between p-nitroacetophenone and diethylamine.

Determine the expected product of the acid-catalysed reaction between cyclopentanone and methylamine.

Determine the expected product of the acid-catalysed reaction between cyclopentanone and pyrrolidine.

Propose a mechanism to show how cyclopentanone reacts with piperidine in the presence of an acid.

Draw the mechanism for the reaction below.

Provide the carbonyl compound and the amine that would combine to produce the derivative below.

The reaction between cyclohexanecarbaldehyde and ethylamine can produce two different imine products.

(i) Give the structures of the two imines.

(ii) Explain why two imines form.

Propose a plausible mechanism for the reversible reaction shown below. Note: diethyl ether is the solvent and HCl gas is a catalyst.

Draw the mechanism for the reaction shown below.

(i) Identify the functional group present in the compound shown below.

(ii) Identify the product of its complete hydrolysis.

(i) Give the functional group present in the following compound.

(ii) Provide the product of its complete hydrolysis.

Provide the starting reactants that would generate the following derivative. Include a carbonyl compound.

Identify the missing products.

Identify the bonds broken and formed in the reaction shown below. Identify whether the reactions are favored or not based on qualitative analysis of the following factors: i) entropy ii) enthalpy iii) overall

Is the formation of a cyanohydrin possible by adding a ketone to a solution of KCN?

In the benzoin condensation, what is the role of the cyanide ion? Why does the reaction fail if the hydroxide ion is used instead?

a) The cyanide ion generates an electrophile, allowing the reaction to occur. If a hydroxide ion is used, the electrophile is not generated, and the reaction will not continue.

b) The cyanide ion deprotonates methanol, allowing the reaction to occur. If a hydroxide ion is used, the methanol is not deprotonated, and the reaction will not continue.

c) The cyanide ion creates an umpolung to the carbonyl carbon, allowing the reaction to occur. If a hydroxide ion is used, the polarity of the carbonyl carbon will not be inverted, and the reaction will not continue.

d) The cyanide ion removes an α-hydrogen, allowing the reaction to occur. If a hydroxide ion is used, the α-hydrogen is not removed, and the reaction will not continue.

Draw the structure of the products formed when cyclopentanone reacts with sodium cyanide.

Determine the carbonyl compound to react with NaCN/HCN to yield the cyanohydrin below.

Provide the starting molecule and the reagent needed to synthesize the cyanohydrin below.

Identify the secondary alcohol produced when cyclopentyl formate reacts with an excess amount of Grignard reagent.

Propose a synthesis scheme for the formation of 1-methylcyclopent-1-ene from cyclopentanol.

Draw a suitable mechanism for the reaction shown below.

Draw the products obtained by the reaction between cyclopentanecarbaldehyde and the reagents shown below.

CH₃MgBr, then H₃O⁺

i) Draw a mechanism for each of the reactions. ii) Which of the two reactions would be considered more sustainable? Note: Assume that the starting organic molecules are equally green.

Which of the following para-substituted benzaldehydes is most likely to be found in the hydrate form in an aqueous solution?

Can the hydration of aldehydes and ketones also be catalyzed by a base instead of an acid? Explain why.

Identify the given compound as one of the following:

Arrange the given compounds in increasing order of their equilibrium constant for hydration (lowest to highest).

Draw the product of the reaction shown below.

Draw the structure of the hemiacetal given below.

• The methyl hemiacetal of acetaldehyde

Name the functional group present in the following compounds and show the products of their complete hydrolysis.

Explain why acetals are used as a carbonyl-protecting group against nucleophilic reagents.

Draw a suitable mechanism for the given reaction.

Which of the following ketones forms a higher percentage of a hydrate?

Identify the given compound as one of the following:

Draw the product of the reaction given below.

Draw a mechanism for the reaction of acetaldehyde with methanol in the presence of an acid.

Draw a mechanism for the hydrolysis of acetone dimethyl acetal in the presence of an acid.

Draw a mechanism for the reaction of acetone with ethylene glycol in the presence of an acid.

Draw the structure of the acetal given below.
a. the ethylene acetal of butan-2-one

Show how the following acetals can be produced using suitable carbonyl compounds and alcohols.

Draw a mechanism for the hydrolysis of cyclopentanone ethylene acetal in the presence of an acid.

Draw a mechanism for the hydrolysis of the acetal given below in the presence of an acid.

Name the functional group present in the following compounds and show the products of their complete hydrolysis.

The heterocyclic rings of nucleosides have aminoacetal linkage with deoxyribose. Box the aminoacetal functional groups in adenosine and thymidine.

Draw the structure of the product formed when benzaldehyde reacts with ethylene glycol in an acidic medium.

Draw the product of the reaction shown below:

The reaction below is unsuccessful in producing the desired alcohol.

How may the reaction conditions be changed to allow the desired alcohol product to form?

Propose the synthesis of the following compound using the given starting material. Please note that the reaction needs a protecting group.

Acetals can be used as protecting groups for aldehydes, ketones, and diols. The acetal formed with acetone and diol is termed acetonide. Draw the structure of acetonide formed by the acid-catalyzed reaction of acetone with the following diol.

It is possible to selectively hydrogenate alkenes with the presence of ketones in the same molecule. Supposing that was not the case, suggest a strategy to generate (i) from (ii) with the use of a protecting group.

Identify the starting materials (including a carbonyl compound) required to form the following structure:

Acetals are used as protecting groups for carbonyl compounds (aldehydes and ketones) and diols. A cyclic acetal is formed when a ketone or an aldehyde reacts with a diol. Determine the cyclic acetal produced when the compound below reacts with ethane-1,2-diol under acid catalysis.

Acetals are used as protecting groups for 1,2-diols and carbonyl compounds (aldehydes and ketones). Formation of an acetal using a diol as an alcohol yields a cyclic acetal. Provide the cyclic acetal formed when the following compound reacts with cyclobutane-1,2-diol under acid catalysis.

Draw the structure of the starting material that would produce the following compound through Fischer indole synthesis.

Identify the carbonyl compound and the amine that would combine to produce the derivative below.

Draw the carbonyl compound and the amine that would combine to produce the derivative below.

Draw the structure of the 3,5-dimethylphenylhydrazone of propiophenone. Disregard stereoisomers.

Provide the structure of the derivative semicarbazone of 2-methylcyclopentanone. Disregard stereoisomers.

Provide the structure of the derivative cyclopentanone oxime.

What is the product for the reaction of cycloheptanone with phenylhydrazine and weak acid?

What is the product formed from the reaction of cyclopentanone and hydroxylamine in the presence of a weak acid?

Propose a suitable mechanism to show how benzyl chloride reacts with two equivalents of isobutylmagnesium bromide.

Provide the product of the reaction shown below.

Provide the sequence of reactions that would change the reactant (on the left) into the product (on the right) using a cuprate reagent. It is indicated how many steps are optimum.

Determine the product generated by the reaction given below.

Provide the organometallic reagent and nitrile that can be used to produce the given ketone. Note there are two possible ways to make it.

Determine the organometallic reagent and nitrile that can be used to produce the given ketone. Note that there are two possible ways to make it.

Propose a plausible mechanism for the hydrolysis of the following magnesium salt to acetone under acidic conditions.

Identify the best pair of phosphonium ylide (derived from an alkyl halide) and carbonyl compound for synthesizing the specified compound via the Wittig reaction.

Determine the best pair of phosphonium ylide (derived from an alkyl halide) and carbonyl compound for synthesizing the desired compound using the Wittig reaction.

What is the best pair of a phosphonium ylide (derived from an alkyl halide) and a carbonyl compound for synthesizing the given alkene?

Show how the following conversion can be achieved with good yield. Use any necessary reagents.

Show how the following conversion can be achieved with good yield. Use any necessary reagents.

Show how the given conversion can be achieved with a good yield. Provide any necessary reagents.

Devise a synthesis for the following alkenes using the Wittig reaction starting with an alkyl halide and a ketone or an aldehyde.

Devise a synthesis for the following alkenes using the Wittig reaction starting with an alkyl halide and a ketone or an aldehyde.

Draw the products of the reaction shown below.

(i) Outline the syntheses shown below, using aldehydes and alkyl halides as your starting materials.

(ii) Show how to make penta-1,3-diene via the formation of the terminal double bond.

Propose a synthetic pathway to prepare the following compound using cyclopentanone as the starting material.

Show how hexanal can be synthesized using the starting material given below with any necessary reagent.

• Hexanoic acid

Show how hexanal can be synthesized using the starting material given below with any necessary reagent.

• Ethyl hexanoate

Show how the following conversion can be carried out using suitable reagents.

Show how the following compounds can be synthesized starting with a reactant having not more than six carbons.

Show how the following conversion can be achieved with good yield. Use any necessary reagents.

Show how the given conversion can be achieved with a good yield. Provide any necessary reagents.

• Propanal → 2-hydroxybutanoic acid

Show how pentanal can be converted to hexan-2-one. Provide any necessary reagents.

Show how hex-1-yne can be converted to hexan-2-one. Provide any necessary reagents.

Show how 2,3-dimethylhex-2-ene can be converted to pentan-2-one. Provide any necessary reagents.

Show how hexan-1-ol can be converted to hexanal. Provide any necessary reagents.

Show how hept-1-ene can be converted to hexanal. Provide any necessary reagents.

The following road map has some missing compounds. Propose the structures for the compounds A through F.

When lactose hydrolyzes, a mixture of galactose and glucose with a ratio of 1:1 has a specific rotation of +134.7°. What is the specific rotation of an equilibrium mixture of galactose? [Note: The specific rotation of glucose at equilibrium is +52.7°.]

Draw the mechanism for the reaction shown below.

Show the reaction mechanism for the reaction shown below.