FiltersDone

Question type

Essay

Multiple Choice

Short Answer

True False

Matching

Exam 19: Aldehydes and Ketones: Nucleophilic Addition Reactions

Show Answer

Share

---

All types

Filters

Study Flashcards

Question 1

Essay

Review LaterAdd Note

Review Later

Draw: 2-cyclohexenone

Correct Answer

verified

Show Answer

Question 2

Essay

Review LaterAdd Note

Review Later

Draw: 5,5-dimethyl-1,3-cyclohexanedione (dimedone)

Correct Answer

verified

Show Answer

Question 3

Essay

Review LaterAdd Note

Draw: trans-3-isopropylcyclohexanecarbaldehyde

Exhibit 19-9 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 (6H,triplet),1.59 δ (4H,multiplet),2.36 δ (4H,triplet) -Refer to Exhibit 19-9.What functional group is indicated by the IR data?

Name:

Exhibit 19-2 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.Unfortunately,when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated. -Refer to Exhibit 19-2.Identify the electrophile in the reaction of benzaldehyde with hydrogen cyanide.

Exhibit 19-10 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, no McLafferty rearrangement fragment ¹H NMR: Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS -Refer to Exhibit 19-10.Propose a structure for this compound.

What is the correct structure for 2-hydroxyacetophenone?

In the Wittig reaction,a phosphorus ylide adds to a ketone or aldehyde to yield an alkene.Write the complete stepwise mechanism for the Wittig reaction shown below.Show all intermediate structures and all electron flow with arrows.

Exhibit 19-3 Consider the reaction below to answer the following question(s). -Refer to Exhibit 19-3.Write the complete stepwise mechanism for this reaction.Show all electron flow with arrows and show all intermediate structures.

Which of the following functional groups does not contain a carbonyl group?

Name:

Exhibit 19-2 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.Unfortunately,when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated. -Refer to Exhibit 19-2.Formulate a reasonable mechanism for the reaction of the cyanohydrin of benzaldeyhe,shown above,with aqueous NaOH.Show all intermediate structures and all electron flow with arrows.

The following substance is heated in the presence of aqueous NaOH.Atoms other than carbon and hydrogen are labeled. The product of the reaction is:

Draw: 2,2,2-trichloroethanal (chloral)

Exhibit 19-1 Consider the reaction below to answer the following question(s): -Refer to Exhibit 19-1.The exact position of the equilibrium between ketones/aldehydes and their hydrates depends on the structure of the carbonyl compound.Although the equilibrium favors the carbonyl compound in most cases,cyclopropanone forms a stable hydrate.Explain this phenomenon based on the structures of cyclopropanone and its hydrate.

Exhibit 19-1 Consider the reaction below to answer the following question(s) : -Refer to Exhibit 19-1.Many nucleophilic addition reactions of aldehydes and ketones are catalyzed by acid or base.Bases catalyze hydration by:

Of the types of reactions that characterize carbonyl groups,how is the following reaction classified?

Which of the labeled peaks would allow the distinction of an aldehyde from a ketone based on this spectrum?

Enamines formed from the cyclic secondary amine pyrrolidine are important intermediates in the synthesis of 1,5-diketones. On the structures provided below,draw arrows showing electron flow for the reaction mechanism for the acetic acid-catalyzed formation of an enamine from cyclohexanone and pyrrolidine.