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Exam 8: Alkenes: Reactions and Synthesis

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Question 1

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Exhibit 8-3 Consider the reaction below to answer the following question(s) . ​ Alkenes may be hydrated by the hydroboration/oxidation procedure shown. ​ -Refer to Exhibit 8-3.Hydroboration of alkenes is an example of:

A) a rearrangement reaction.
B) a substitution reaction.
C) an elimination reaction.
D) an addition reaction.

E) C) and D)
F) None of the above

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Question 2

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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.Draw the structure of A.

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Question 3

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Consider the following polymer. Draw the condensed formula for its monomer.

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.Draw the complete Lewis electron dot structure for dichlorocarbene,CCl₂.

Exhibit 8-3 Consider the reaction below to answer the following question(s) . ​ Alkenes may be hydrated by the hydroboration/oxidation procedure shown. ​ -Refer to Exhibit 8-3.The intermediate formed in the first step of this reaction is:

Consider the polymeric structure below for amylose (a type of starch).Draw a box around the monomer of amylose.Extra: Propose a structure for the monomer.Hint: This polymer is formed in a dehydration reaction.

Exhibit 8-3 Consider the reaction below to answer the following question(s) . ​ Alkenes may be hydrated by the hydroboration/oxidation procedure shown. ​ -Refer to Exhibit 8-3.Hydroboration/oxidation of alkenes occurs with:

Povidone is produced commercially as a series of products having mean molecular weights ranging from about 10,000 to 700,000.Complexed with iodine,povidone yields an iodophor,marketed under the tradename Betadine,which is used as a topical anti-infective. Identify the monomer unit(s) in povidone.

Draw the skeletal structure(s) and name the product(s) of the reaction when the following substance is treated with sulfuric acid and warmed to approximately 50 °C.Atoms other than hydrogen and carbon are labeled.

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.What was the other product formed in the KMnO₄ oxidation of B?

Hydration of an alkene during enzyme catalysis in a biological system produces an optically active product even through there is a potential to form a racemic mixture.Explain why this occurs.

Draw both chair conformations of trans-1,2-dichlorocyclohexane on the templates provided below.Circle the least stable conformation.

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.Since the two chlorine atoms add to opposite faces of the cyclohexene double bond,we say that the reaction occurs with:

Draw a condensed formula for a polymer containing five repeating units derived from the following monomer.Name the polymer.

​Draw the mechanism of the bromination of 3-hexene in the presence of water via bromohydrin formation.

Consider the following intermediate. Which is applicable to this structure?

Exhibit 8-3 Consider the reaction below to answer the following question(s) . ​ Alkenes may be hydrated by the hydroboration/oxidation procedure shown. ​ -Refer to Exhibit 8-3.The regiochemistry of hydroboration/oxidation of alkenes is:

Which of the following will not undergo catalytic reduction in the presence of H₂ and metal catalyst?

​Draw the mechanism of the epoxidation of 2-butene using a halohydrin.

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.The reaction of an alkene with dichlorocarbene is: