Questions and Answers of Organic Chemistry 6th

Give the products expected when each of the following alkenes is subjected to oxymercuration–reduction.(a) Cyclohexene (b) 2-methyl-2-pentene (c) Trans-4-methyl-2-pentene
Give the product(s) expected from the hydroboration–oxidation of each of the following alkenes.(a) Cyclohexene (b) 2-methyl-2-pentene (c) Trans-4-methyl-2-pentene (d) Cis-3-hexene
Ozonolysis of 2-pentene gives a mixture of the following three ozonides. Using the mechanism in Eqs. 5.36a and 5.36b, explain the origin of all three ozonides. H₂C-HC A CH-CH3
From what alkene and by which methods could you prepare each of the following alcohols essentially free of constitutional isomers? (a) OH (b) LOH (c) Et3C-OH (Hint: Draw out the structure!)
Indicate whether each of the following reactions is homolytic or heterolytic, and tell how you know. Write the appropriate fishhook or curved-arrow notation for each. (a) :N=C:+
In the presence of light, the addition of Br2 to alkenes can occur by a free-radical mechanism rather than a bromonium-ion mechanism. Write a free-radical chain mechanism that shows the propagation
Give the principal organic products expected when 1-butene reacts with each of the following reagents. (a) Br₂ in CH₂Cl₂ solvent (b) 03, -78 °C (c) product of (b) with (CH3)2S (d) product of
Give the structure the organic product(s) formed when HBr reacts with each of the following alkenes in the presence of peroxides, and explain your reasoning. If more than one product is formed,
Draw the structure of (a) A six-carbon alkene that would give the same product from reaction with HBr whether peroxides are present or not.(b) Four compounds of formula C10H16 that would undergo
Repeat Problem 5.27 for 1-ethylcyclopentene.Problem 5.27Give the principal organic products expected when 1-butene reacts with each of the following reagents. (a) Br₂ in CH₂Cl₂ solvent (b) 03,
Using the mechanism of the oxymercuration reaction to guide you, predict the product(s) obtained when 1-hexene is treated with mercuric acetate in each of the following solvents and the resulting
Using the mechanism of halogen addition to alkenes to guide you, predict the product(s) obtained when 2-methyl-1-butene is subjected to each of the following conditions.Explain your answers.(a) Br2
Trifluoroiodomethane undergoes an addition to alkenes in the presence of light by a free-radical chain mechanism.The initiation step of this reaction is the light-induced homolysis of the C—I
In thermal cracking (Sec. 5.8), bonds generally break homolytically.(a) In the thermal cracking of 2,2,3,3-tetra me thylbutane, which bond would be most likely to break? Explain.(b) Which compound,
(a) What product would be obtained from the ozonolysis of natural rubber, followed by reaction with H2O2?(b) Gutta-percha is a natural polymer that gives the same ozonolysis product as natural
Free-radical addition of thiols (molecules with the general structure RSH) to alkenes is a well-known reaction, and it is initiated by peroxides.(a) Use information found in tables in this chapter
The halogenation of methane in the gas phase is an industrial method for the preparation of certain alkyl halides and takes place by the following equation (X = halogen):(a) This reaction takes place
The mechanism for the free-radical polymerization of ethylene shown in Eqs. 5.72a–c (pp. 217–218) is somewhat simplified because it does not account for the observation that low-density
Polypropylene carbonate is considered to be a “green” polymer because it is made from CO2 and is biodegradable.Draw out the structure of polypropylene carbonate for n = 3. (Leave the “dangling
Using the curved-arrow or fishhook notation, as appropriate, suggest mechanisms for each of the reactions given in Fig. P5.49. (a) H₂C (b) H3C C-CH₂ CH₂CH=CH₂ H₂C CH₂ T T HO OH C#yan +
Consider the reaction of a methyl radical (·CH3) with the p bond of an alkene:The relative rates of the reaction shown in Fig. P5.50 were determined for various alkenes.(a) Draw the free-radical
Equations 5.25a–c on p. 193 show the formation of trialkylboranes from alkenes and BH3. In the reaction of 2,3-dimethyl-2-butene with BH3, only two equivalents of the alkene react, even with a
When trans-3-hexene is subjected to ozonolysis in the presence of an excess of acetaldehyde containing the isotope 18O, an ozonide is isolated that contains the isotope at one of the oxygens. Use the
Isobutylene (2-methylpropene) can be polymerized by treating it with liquid HF as shown in Fig. P5.53. A small amount of tert-butyl fluoride is formed in the reaction. Suggest a curved-arrow

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