Exam 14: Aldehydes and Ketones: Nucleophilic Addition Reactions

Consider the data below to answer the following question(s). Cyanohydrins are important intermediates in the synthesis of α-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. Identify the electrophile and nucloephile in the reaction of benzaldehyde with hydrogen cyanide.

Which of the following would correctly describe the respective ¹³C NMR and ¹H NMR spectra for the indicated atoms for the compound shown below?

What is the IUPAC name of the following compound?

What is the correct assignment of the functional groups in each of the following compounds?

Draw structures corresponding to each of the following names. -Draw: cyclohexen-2-one

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

Draw structures corresponding to each of the following names. -Draw: benzophenone

Synthesize the following alkene through the Wittig reaction of a carbonyl compound and a phosphorus ylide.

Provide IUPAC names for each structure below. -Name:

α,β-Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the β carbon, as shown below. Use this information to answer the following question(s). -Refer to instructions. This reaction is called a(n) _____ reaction.

In the box, what is the name of the reactant used in the following reaction?

Predict whether the following reactions of the depicted carbonyl containing compounds and amines will result in the formation of an enamine or an imine. A B C

Consider the data below to answer the following question(s). C₇H₁₄O IR: 1715 cm−¹ MS: M⁺ at m/z = 114, α-cleavage fragment at m/z = 71. McLafferty rearrangement fragment at m/z = 86. ¹H NMR: 0.92 δ (6 H, triplet), 1.59 δ (4 H, multiplet), 2.36 δ (4 H, triplet) -Refer to instructions. Interpret the ¹H NMR data.

Consider the data below to answer the following question(s). Cyanohydrins are important intermediates in the synthesis of α-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.

Consider the data below to answer the following question(s). C₇H₁₄O IR: 1715 cm−¹ MS: M⁺ at m/z = 114, α-cleavage fragment at m/z = 71. McLafferty rearrangement fragment at m/z = 86. ¹H NMR: 0.92 δ (6 H, triplet), 1.59 δ (4 H, multiplet), 2.36 δ (4 H, triplet) -Refer to instructions. Interpret the mass spectral data.

The nucleophillic addition of water to an aldehyde or ketone