Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 10, Problem 2LGP
(a) Propose a synthesis of 2-methoxypropene starting with propane and methane as the sole source for carbon atoms. You may use any other reagents necessary. Devise a rettrosynthetic analysis first.
(b) 2-Methoxypropene will form a
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Chlorination of 2-butanone yields two isomeric products, each having the molecular formula C4H7ClO. (a) What are these two compounds? (b) Write structural formulas for the enol intermediates that lead to each of these compounds. (c) Using curved arrows, show the flow of electrons in the reaction of each of the enols with Cl2.
An equimolar blend of 1,4-hydroquinone diallylether and ethylene glycol
dimercaptoacetate containing a small amount of benzophenone (radical photoinitiator)
is polymerized by irradiating the blend with ultraviolet (UV) light.
(a) Write a balanced chemical equation for the polymerization.
(b) How would you classify this polymerization according to the reaction
mechanism?
(c) Calculate the extent of reaction needed to produce a polymer with a number
average molar mass of 20,000 g/mole (neglect the effect of end groups in the
calculation).
(d) Draw the structure of the polymer that is obtained when the mole ratio of diallyl
ether to dithiol is 1.1.
(e) Explain briefly the consequences of including a tetrafunctional thiol in the
polymerization with the exact stoichiometry 2:1:4 of difunctional thiol to
tetrafunctional thiol to difunctional allylic ether.
HS
HS
1,4-hydroquinone diallylether
Ethylene glycol dimercaptoacetate
2. Using 1-butyne as the starting material, write the necessary reactions to convert to the indicated
products.
(a)
Butane
(b)
1-Butene
(c)
2,2-Dibromobutane
(d)
2-Pentane
3. Show how 2-butyne can be converted into 2-butene.
4. Using propyne as the starting material, carry out the following reaction sequences to give the
following products.
(a)
2-Butyne
(b)
2-Butene
(c)
2-Bromobutane
(d)
Pentane
Chapter 10 Solutions
Organic Chemistry
Ch. 10 - Prob. 1PPCh. 10 - Prob. 2PPCh. 10 - Practice Problem 10.3 How would the molecular ion...Ch. 10 - Prob. 4PPCh. 10 - Prob. 5PPCh. 10 - Prob. 6PPCh. 10 - Practice Problem 10.7 Chlorination reactions of...Ch. 10 - Prob. 8PPCh. 10 - Prob. 9PPCh. 10 - Prob. 10PP
Ch. 10 - Prob. 11PPCh. 10 - Practice Problem 10.12 Benzylic radicals, due to...Ch. 10 - Prob. 13PPCh. 10 - Practice Problem 10.14 Show how the following...Ch. 10 - Prob. 15PPCh. 10 - Prob. 16PPCh. 10 - Prob. 17PPCh. 10 - Prob. 18PCh. 10 - Explain the relative distribution of produces...Ch. 10 - 10.20 Which of the following compounds can be...Ch. 10 - Prob. 21PCh. 10 - Prob. 22PCh. 10 - Prob. 23PCh. 10 - Prob. 24PCh. 10 - 10.25 List in order of decreasing stability all of...Ch. 10 - Prob. 26PCh. 10 - Prob. 27PCh. 10 - Prob. 28PCh. 10 - Starting with the compound or compounds indicated...Ch. 10 - Prob. 30PCh. 10 - 10.31 Synthesize each of the following compounds...Ch. 10 - Synthesize each of die following compounds by...Ch. 10 - Prob. 33PCh. 10 - Prob. 34PCh. 10 - Prob. 36PCh. 10 - The halogen atom of an alkyl halide can be...Ch. 10 - Prob. 38PCh. 10 - Prob. 39PCh. 10 - Write a mechanism for the following reaction.Ch. 10 - 10.41 Hydrogen peroxide and ferrous sulfate react...Ch. 10 - Prob. 42PCh. 10 - If one were to try to draw the simplest Lewis...Ch. 10 - Prob. 1LGPCh. 10 - 2. (a) Propose a synthesis of 2-methoxypropene...
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- 2. Using 1-butyne as the starting material, write the necessary reactions to convert to the indicated products. (a) Butane (b) 1-Butene (c) 2,2-Dibromobutane (d) 2-Pentane 3. Show how 2-butyne can be converted into 2-butene. 4. Using propyne as the starting material, carry out the following reaction sequences to give the following products. (a) 2-Butyne (b) 2-Butene (c) 2-Bromobutane (d) Pentane 5. How does one convert 1-pentene to 1-pentyne? 1-Bromobutane to 1-butyne?arrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) 1 Ph THF A Ph Ph B H₂SO4 100 °C 3 OH What is the name of the reaction that is followed by reaction Method A?arrow_forwardBiphenyl has the following structure.(a) Is biphenyl a (fused) polynuclear aromatic hydrocarbon?(b) How many pi electrons are there in the two aromatic rings of biphenyl? How does this number compare with that for naphthalene?(c) The heat of hydrogenation for biphenyl is about 418 kJ>mol (100 kcal>mol). Calculate theresonance energy of biphenyl.(d) Compare the resonance energy of biphenyl with that of naphthalene and with that of two benzene rings. Explain thedifference in the resonance energies of naphthalene and biphenyl.arrow_forward
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- Photochemical chlorination of 2,2,4-trimethylpentane gives four isomeric monochlorides. (a) Write structural formulas for these four isomers. (b) The two primary chlorides make up 65% of the monochloride fraction. Assuming that all the primary hydrogens in 2,2,4-trimethylpentane are equally reactive, estimate the percentage of each of the two primary chlorides in the product mixture.arrow_forward(1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case?arrow_forwardSuggest a method of preparing ethyl benzene, starting with benzene and ethylene as the only organic reagents.arrow_forward
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