Exam 9: Aldehydes and Ketones: Nucleophilic Addition Reactions

Instructions: Provide IUPAC names for each structure below. -Name:

The nucleophillic addition of water to an aldehyde or ketone

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

Instructions: Provide IUPAC names for each structure below. -Name:

Propose a synthesis of Dimestrol starting from p-methoxypropiophenone as the only source of carbon.

Instructions: Predict the products from the information given for the following question(s). -Predict:

Instructions: Draw structures corresponding to each of the following names. -Draw: 2,2-dimethylcyclopentane-1,3-dione

Instructions: Predict the products from the information given for the following question(s). -Predict:

Predict the products of the following reactions.

Instructions: Consider the reaction below to answer the following question. -Refer to instructions. The product of this reaction is called:

Instructions: Draw structures corresponding to each of the following names. -Draw: trans-3-isopropylcyclohexanecarbaldehyde

Instructions: Predict the products from the information given for the following question(s). -Predict:

Predict the products of the following reactions.

The substance formed in the following reaction is called:

Instructions: Draw structures corresponding to each of the following names. -Draw: cyclohex-2-enone

Instructions: $\alpha$ , $\beta$ -Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the $\beta$ carbon, as shown below. Use this information to answer the following question(s). -Refer to instructions. Draw a resonance form for the unsaturated carbonyl that accounts for this reactivity.

What is the IUPAC name of the following compound?

Instructions: Draw structures corresponding to each of the following names. -Draw: 5,5-dimethylcyclohexane-1,3-dione (dimedone)

Instructions: Consider the reaction below to answer the following question. -Refer to instructions. The electrophile, the nucleophile and the catalyst in this reaction are indicated by letters _____, _____, and _____, respectively.

Instructions: Consider the data below to answer the following question(s). Cyanohydrins are important intermediates in the synthesis of $\alpha$ -hydroxycarboxylic acids from ketones and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. When a cyanohydrin is treated with aqueous base, however, the original carbonyl compound is isolated. -Refer to instructions. The reaction of an aldehyde with hydrogen cyanide is an example of _____ reaction.