Exam 22: Carbonyl Alpha-Substitution Reactions

Exhibit 22-3 Consider the reaction below to answer the following question(s). -Refer to Exhibit 22-3.On the structures provided above,draw arrows indicating electron flow in the generation of the intermediate C.

Exhibit 22-4 Consider the reaction sequence below to answer the following question(s): -Refer to Exhibit 22-4.Write the complete stepwise mechanism for the conversion of Compound X into Compound Y.Show all electron flow with arrows and draw all intermediate structures.

Exhibit 22-5 Consider the reaction sequence below to answer the following question(s): -Refer to Exhibit 22-5.Conversion of B into C involves hydrolysis of the ester followed by decarboxylation.On the structures provided below,show the electron flow for the decarboxylation step.

Exhibit 22-5 Consider the reaction sequence below to answer the following question(s): -Refer to Exhibit 22-5.The initial product formed on decarboxylation is an enol,which rapidly equilibrates to its keto form under the acidic reaction conditions.Write the complete stepwise mechanism for the acid-catalyzed conversion of the enol into its keto form,Compound C.

Exhibit 22-5 Consider the reaction sequence below to answer the following question(s): -Refer to Exhibit 22-5.Conversion of A into B is a type of reaction termed _____.

Exhibit 22-5 Consider the reaction sequence below to answer the following question(s): -Refer to Exhibit 22-5.The starting material A in this reaction sequence is called _____.

Exhibit 22-2 Consider the structures below to answer the following question(s). -Refer to Exhibit 22-2.Indicate the most acidic hydrogens in each of the molecules.

The alkyl halide that should be used to produce octanoic acid via the malonic ester synthesis is:

Exhibit 22-3 Consider the reaction below to answer the following question(s). -Refer to Exhibit 22-3.The strongest base in the reaction is:

Exhibit 22-2 Consider the structures below to answer the following question(s). -Rank the molecules above in order of increasing acidity (least acidic to most acidic).

Examine the following generalized structure. This represents

Exhibit 22-6 Consider the reaction below to answer the following question(s): -Refer to Exhibit 22-6.Write the complete stepwise mechanism for the reaction above.Show all intermediate structures and all electron flow with arrows.

Draw the structure of the major product formed when the substance represented by the following molecular model is treated with: 1.Br₂/acetic acid,2.pyridine/heat.Atoms of other than carbon and hydrogen are labeled.

Exhibit 22-1 Refer to the compounds below to answer the following question(s): -Refer to Exhibit 22-1.Choose the most acidic compound from Compounds I - IV.Explain your choice.

Nitroethane [CH₃CH₂NO₂,pK_a = 8.6] is a much stronger acid than ethane [CH₃CH₃,pK_a ≈ 60].Explain.

Exhibit 22-4 Consider the reaction sequence below to answer the following question(s): -Refer to Exhibit 22-4.Below are the structures and electron flow for the conversion of Compound Y into Compound Z.Draw the structure of Compound Z.(Hint: Compound Z is an alcohol. )

Write the complete stepwise mechanism for the reaction of cyclopentanone with bromine in acetic acid to give 2-bromocyclopentanone.Show all intermediate structures and all electron flow with arrows.

Exhibit 22-1 Refer to the compounds below to answer the following question(s): -Indicate which hydrogens in Compound II are the most acidic.Explain your answer.

Exhibit 22-1 Refer to the compounds below to answer the following question(s): -Refer to Exhibit 22-1.Draw the structures for all enols of Compound I.

Which of the hydrogen atoms indicated by a number is the most acidic in the structure below? Atoms other than carbon and hydrogen are labeled.