Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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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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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
(b) 3-methyl-2-butanol reacts with concentrated sulphuric acid to form 2-methyl-2-
butene. Write the mechanism for the reaction.
(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?
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 - 10.32 Synthesize each of the following compounds...Ch. 10 - Prob. 33PCh. 10 - Prob. 34PCh. 10 - Prob. 35PCh. 10 - Write a mechanism for the following reaction.Ch. 10 - Prob. 37PCh. 10 - The halogen atom of an alkyl halide can be...Ch. 10 - Prob. 39PCh. 10 - Prob. 40PCh. 10 - If one were to try to draw the simplest Lewis...Ch. 10 - Prob. 1LGPCh. 10 - 2. (a) Propose a synthesis of 2-methoxypropene...Ch. 10 - Use the single-bond dissociation energies of Table...Ch. 10 - 10.2 In the radical chlorination of methane, one...Ch. 10 - Prob. 3QCh. 10 - Use the single-bond dissociation energies of Table...Ch. 10 - Prob. 5QCh. 10 - Prob. 6Q
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- (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) Ph Ph 8*8 Ph THF A 1 Santande B H₂SO4 100 °C 3 OH Using curly arrows, provide full mechanistic details accounting how methylenecyclohexane 2 was synthesised according to both Methods A and B.arrow_forward(b) Answer BOTH parts (i) and (ii). (i) Using your knowledge of silicon chemistry, explain why the synthesis of a compound containing a formal Si=0 double bond is challenging. (ii)Bearing in mind your answer to part (i), suggest a synthetic route to a silanone, R2Si=O, starting from silicon tetrachloride SiCl4 and using any other reagents you choose. Identify all reagents and side-products in your synthetic route and specify your chosen R group, giving reasons for your choice.arrow_forward3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) the same quantities of reagents are dissolved in half the volume of methanol (b) 3-bromo-2-methylpropene is used in place of 3-chloro-2-methylpropene (c) sodium methanethiolate (CH3SNa) is used in place of of sodium methoxidearrow_forward
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