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Exam 10: Free-Radical Reactions, Main-Group Organometallic Compounds, and Carbenes

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Question 1

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Complete the reactions by giving the structure of the missing organic products.

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11edaded_7d3e_909b_a31a_ef33b61aceae_TBMC1048_00

Question 2

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Draw the correct product for each of the reactions:

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Question 3

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Outline a synthesis of this product.

Identify the stereochemistry of the polymers.

1-Methyl-1-vinyl cyclopentane undergoes addition of HBr under two different conditions as shown in the two pathways. A mixture of products is obtained in Pathway A, whereas a single product is obtained in pathway

Devise a synthesis to achieve the transformation.

Provide the structures of the missing compounds.

Treatment of (+)-(R)-3-methyl-1-pentene with HBr and peroxides yields (-)-1-bromo-3-methyl pentane. Determine the stereochemical configuration of the product.

Complete the reaction by giving the missing product.

Give the product A that results when HBr undergoes peroxide-mediated addition to 1-methylcyclopentene. Also give the structure of the free-radical intermediate B (other than Br.) in the propagation steps of this reaction.

Free-radical polymerization of ethylene proceeds with the following propagation steps. It turns out that polyethylene made by free-radical polymerization contains some branches, for example, (a) Give a plausible mechanism, complete with "fishhooks," for propagation steps that can account for formation of these branches. (b) It is possible (by a completely different method) to form polyethylene with unbranched chains. Which do you think would have higher density, branched-chain polyethylene or polyethylene with unbranched chains? Explain briefly.

Give the structure of the organic free-radical intermediate formed in the propagation steps in the reaction of the alkene with HBr in the presence of peroxides.

A free-radical addition of a certain compound X-Y to an alkene (R = alkyl) results in the conversion: The first propagation step in the mechanism is Therefore, what is the second propagation step in the mechanism?

Predict the major organic product of the reaction:

Thiols (R-S-H) undergo addition to alkenes but only in the presence of peroxides. This equation is an example. $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { C } = \mathrm { CH } _ { 2 } + \mathrm { RSH } \stackrel { \text { peroxides } } { \longrightarrow } \left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CH } - \mathrm { CH } _ { 2 } \mathrm { SR }$ Which one of these is a reactive intermediate in this reaction? (a) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { C } - \dot { \mathrm { C } } \mathrm { H } _ { 2 } - \mathrm { SR }$ (b) (c) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \stackrel { + } { \mathrm { C } } - \mathrm { CH } _ { 2 } - \mathrm { SR }$ (d) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \dot { \mathrm { C } } - \mathrm { CH } _ { 2 } - \mathrm { SR }$ (e) (f) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \dot { \mathrm { C } } - \mathrm { CH } _ { 2 } - \mathrm { SH }$

Complete the reactions by giving the structure of the missing organic products.

Complete the reaction by giving the major organic product(s).

Outline a multi-step synthesis of 4-octanone from 1-pentyne and any other reagents. (Show the reagents required for each step, and the product of each step. Don't show the mechanism.)

Provide the major organic product for the reaction.

Consider this addition polymer, called poly(methyl methacrylate). What is the structure of the monomer from which this polymer is formed by free-radical alkene polymerization?