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Determine the structure of the compounds corresponding to i-iv for each of the following reactions:
Consider the following compound that has been labeled with the O-18 isotope of oxygen.
Write a plausible mechanism for the hydrolysis of this compound under acidic conditions.
Complete the given reactions.
Propose a mechanism for the acid-catalyzed transesterification reaction shown below.
5-hydroxy-3-methylpentanoic acid forms a cyclic ester (lactone) when it is mixed with a trace amount of acid.
(i) Write the structure of the lactone.
(ii) Suggest a plausible mechanism for its formation.
Provide a synthetic pathway to prepare the following compound using the given starting material.
Decarboxylation of esters can alternatively be conducted under basic conditions. Propose a mechanism for the reaction shown below. [Hint: The formation of chloromethane proceeds by an SN2 reaction.]
Draw the structure of the enol tautomer of the compound given below.
Arrange the following compounds according to decreasing enol content and give the most stable enol for each compound.
Predict the product of the reaction given below.
Draw an appropriate mechanism to demonstrate the base-promoted chlorination of acetone in the example below.
Predict the product of the reaction given below.
Show how the following ketone can be produced by alkylating the given carboxylic acid.
Show how the given compound can be prepared starting with cyclopentanone.
Give the possible major product of the given reaction.
Give the major product of the following reaction.
Draw the main product of the reaction shown below.
Provide the final products after the hydrolysis and decarboxylation of the compound shown below.
Determine the major product of the reaction below.
Suggest the plausible product(s) for the crossed aldol condensation reaction below, showing both the products before and after dehydration. (Ignore stereochemistry.)
Show the missing reagents in the given synthesis.
Knoevenagel condensation is a form of aldol condensation that involves the reaction between an active methylene group and an aldehyde or ketone to produce new C=C using amine base as a catalyst. Give the starting materials that are needed for this type of condensation to make the following compound.
A substituted cyclohexanone undergoes base-catalyzed aldol cyclization and gives the following compound. Propose the mechanism of the cyclization to form the product.
What is the anticipated product of the given reaction?
The reaction of lawsone and 4-chloro-2-aminophenol produces the red product shown below. Propose a mechanism for the reaction.
Suggest carbonyl compounds that can be used to synthesize the following Robinson annulation product. Hint: The cyclohexenone is the new ring formed and the double bond of the cyclohexenone is formed by the aldol with dehydration. (Ignore stereochemistry)
