Exam 8: Alkenes: Reactions and Synthesis

Exhibit 8-2 Consider the reaction sequence below to answer the following question(s): ​ -Refer to Exhibit 8-2.Write the complete reaction mechanism for the first step of this reaction sequence.Show all electron flow with arrows and show all intermediate structures.

In the formation of an addition polymer such as polyvinylchloride,

Which of the following is a difference between hydroboration/oxidation and oxymercuration?

Exhibit 8-9 To answer the question(s) below consider the following information: ​ In an abandoned laboratory has been found a flammable liquid,A,in a bottle bearing only the label "Compound A: C₇H₁₂." Government agents have offered you a considerable sum to determine the structure of this compound.After verifying the molecular formula by elemental analysis,you find that Compound A reacts with 1 mol equiv of hydrogen;and,after treatment with acidic KMnO₄,Compound A gives the dicarboxylic acid C (see below).Another bottle from the same laboratory is labeled "Compound B (isomer of A)." Compound B also reacts with 1 mol equiv of hydrogen,but yields cyclohexanone after treatment with acidic KMnO₄. ​ -Refer to Exhibit 8-9.Suggest structures for A and B.

Exhibit 8-1 To answer the question(s) below consider the following reaction: ​ When cyclohexene reacts with chlorine in carbon tetrachloride the trans-dihalide is formed. ​ -Refer to Exhibit 8-1.Write the complete stepwise mechanism for this reaction.Be sure to show all intermediate structures and all electron flow using arrows.

​Draw the mechanism of the hydration of 2-methyl-propene.

Lyapolate Sodium,whose structure is shown below,is used as an anticoagulant.Identify the monomer unit(s) in lyapolate sodium.

Exhibit 8-2 Consider the reaction sequence below to answer the following question(s): ​ -Refer to Exhibit 8-2.In the second step of this reaction sequence,the organomercury compound is treated with sodium borohydride,NaBH₄,to yield the alcohol product.This replacement of a carbon-mercury bond with a carbon-hydrogen bond is termed:

Exhibit 8-1 To answer the question(s) below consider the following reaction: ​ When cyclohexene reacts with chlorine in carbon tetrachloride the trans-dihalide is formed. ​ -Provide the IUPAC name for the product of the reaction of cyclohexene with chlorine.

Exhibit 8-5 The sequence of (1) alkene hydroxylation followed by (2) diol cleavage is often an excellent alternative to direct alkene cleavage with ozone.For this sequence below,answer the following question(s). ​ -Refer to Exhibit 8-5.Give the formula for reagent B.

Consider partial hydrogenation of the following substance. Which of the following describes this reaction?

Exhibit 8-1 To answer the question(s) below consider the following reaction: ​ When cyclohexene reacts with chlorine in carbon tetrachloride the trans-dihalide is formed. ​ -Refer to Exhibit 8-1.The observed stereochemistry of addition of chlorine to cyclohexene is explained by the intermediacy of a:

Exhibit 8-9 To answer the question(s) below consider the following information: ​ In an abandoned laboratory has been found a flammable liquid,A,in a bottle bearing only the label "Compound A: C₇H₁₂." Government agents have offered you a considerable sum to determine the structure of this compound.After verifying the molecular formula by elemental analysis,you find that Compound A reacts with 1 mol equiv of hydrogen;and,after treatment with acidic KMnO₄,Compound A gives the dicarboxylic acid C (see below).Another bottle from the same laboratory is labeled "Compound B (isomer of A)." Compound B also reacts with 1 mol equiv of hydrogen,but yields cyclohexanone after treatment with acidic KMnO₄. ​ -Refer to Exhibit 8-9.How many degrees of unsaturation does Compound A possess?

Exhibit 8-4 Consider the reaction below to answer the following question(s). ​ When dichlorocarbene is generated in the presence of an alkene,a dichlorocyclopropane is formed. ​ -Refer to Exhibit 8-4.Write the complete stepwise mechanism for the formation of dichlorocarbene,CCl₂.Show all intermediate structures and show all electron flow with arrows.

Draw the product(s) of the reaction of (R)-3-chlorobutene with HBr.Indicate stereochemistry.

Exhibit 8-4 Consider the reaction below to answer the following question(s). ​ When dichlorocarbene is generated in the presence of an alkene,a dichlorocyclopropane is formed. ​ -Refer to Exhibit 8-4.In the reaction of an alkene with dichlorocarbene,the dichlorocarbene is the:

Hydration of 4-methyl-1-pentene in the presence of an acid catalyst produces a product that is optically inactive.Briefly explain why.

Which of the following is a carbene?

Draw the skeletal structure(s) and name the product(s) of the reaction when the following substance is treated with ethanoic KOH.Atoms other than hydrogen and carbon are labeled.

What product forms when the following substance is treated with chloroform in the presence of KOH?