Acetals

Acetals Additional Practice Problems

Provide the missing product. Show only one most preferred product. Consider only monosubstitution for EAS where appropriate.

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For the reaction below, draw the structure of the appropriate compound in the box provided. Indicate stereochemistry where it is pertinent.

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Propose a detailed mechanism for the following transformations. Show all possible resonance forms that contribute to this reaction pathway.

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Which of the following compounds is an acetal?

A) I

B) II

C) III

D) IV

E) None of these

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What is the product of the reaction shown below (Hint: hydrate formation under acidic conditions)?

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Propose an electron push mechanism for the following transformation. Be sure to use the correct arrow formalism and correct formal charges

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Draw the product of the reaction of 3-heptanone and two equivalents of 2-propanol.

 

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Which of the following is an acetal?

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Draw the mechanism for the following reaction. Draw all the arrows to indicate movement of the all electrons, write all lone pairs, all formal charges, and all products for each step.

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Complete the mechanism for the following acetal formation reaction. Be sure to show arrows to indicate movement of all electrons, write all lone pairs, all formal charges, and all the products for each step. Remember, I said all the products for each step. IF A NEW CHIRAL CENTER IS CREATED MARK IT WITH AN ASTERISK AND WRITE RACEMIC IF APPROPRIATE . Do not draw arrows to indicate how one contributing structure relates to the other.

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Predict the major product for the following reaction paying attention to the regio- and stereochemistry.

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Provide a mechanism for the following transformation. Show all important flows of electrons, charges and intermediates. 

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Predict the major product for the following reaction, paying attention to the regio- and stereochemistry where appropriate. 

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Predict the major product(s) in the following reaction.

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Which acetal is derived from a ketone?

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Draw the structural formula of the major organic product(s) in the boxes provided for the following reaction.

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The compound shown below is a wasp pheromone. Draw the major product formed when this compound is hydrolyzed in aqueous acid. 

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Consider the three constitutional isomers of dioxane (C 4H8O2), shown below.

One of these constitutional isomers is stable under basic conditions, as well as mildly acidic conditions, and is therefore used as a common solvent. Another isomer is stable under basic conditions, but undergoes hydrolysis under mildly acidic conditions. The remaining isomer is extremely unstable and potentially explosive. Identify each isomer and carefully explain the properties of each compound.

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Suggest a reasonable mechanism for the following spirocyclic acetal formation. Use curved arrows to show electron flow.

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What products result from treating the compound shown with aqueous acid?

(a) Acetone and 1,3-propanediol

(b) Propanedial and 2-propanol

(c) Propanedial and 2,2-propanediol

(e) None of the above

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