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Exam 14: Aldehydes and Ketones: Nucleophilic Addition Reactions

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Question 1

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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.

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Question 2

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Draw the structure of the product obtained from the following reaction.

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11eab600_0838_64c9_9625_2b7f14ac68a4_TB6688_00

Question 3

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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. Propose a structure consistent with the spectral data presented above.

Draw the product(s) of the following reaction.

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.

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. Draw a resonance form for the unsaturated carbonyl that accounts for this reactivity.

What hemiacetal would form from the internal nucleophillic addition reaction of the following compound?

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

Based on the following IR spectrum,

Consider the reaction below to answer the following question. -Many nucleophilic addition reactions of aldehydes and ketones are catalyzed by acid or base. Bases catalyze hydration by:

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

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. What functional group is indicated by the IR data?

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. Calculate the degree of unsaturation for this compound.

Predict the products of the following reactions.

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

What is the IUPAC name of the following compound?

Consider the reaction below to answer the following question. -The substance formed in the following reaction is called:

Predict the products of the following reactions.

What is the name of the major organic product obtained from the following reaction?

Provide IUPAC names for each structure below. -Name: