Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 10, Problem 13PP
Interpretation Introduction
Interpretation:
Radicals leading to the formation of products in the reaction of propylbenzene with chlorine, in the presence of UV-radiation, are to be written. Also, the formation of 1-chloro
Concept Introduction:
Radical reactions are those reactions which take place between free radicals in the presence of light energy. In these reactions, changes in bonding occur with hemolysis.
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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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- Free‑radical halogenation can occur with chlorine and a source of direct UV radiation or sunlight. Chlorination of 2,4‑dimethylpentane via radical halogenation leads to the formation of all three of the products shown. Estimate the relative percentages of each product that will be formed using this means of halogenation. Presume that 1 equivalent of chlorine is used.arrow_forward(c) A series of dialkyl ethers react with excess hydrogen bromide, with the following results. Analyze the ether in each case and write out the complete chemical equations. (1) Ether gives a mixture of bromocyclopentane and 1-bromoethane. (ii) Another ether gives one mole of 1,5-dibromopentane per mole of ether.arrow_forwardThe compound below is treated with chlorine in the presence of light. CH3CH2CH2CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond.arrow_forward
- Deuterium (D, or 2H) is an isotope of hydrogen with atomic mass=2. Deuterium can be introduced into organic compounds by using reagents in which hydrogen has been replaced by deuterium. Outline preparation of the following compounds from the same alkene using appropriate deuterium-containing reagents.arrow_forward(9) SN2 Reactions - Predicting Reaction Products. Complete the reactions shown below by drawing the structure of the substitution product. It is not necessary to balance the equations. Draw the proper product stereochemistry, if relevant (inversion of configuration for SN2). acetone NaCI Br DMF NaOH (b) acetone (c) NaCNarrow_forwardPhenol reacts with three equivalents of bromine in CCl4 (in the dark) to give a product of formula C6H3OBr3. When thisproduct is added to bromine water, a yellow solid of molecular formula C6H2OBr4 precipitates out of the solution. The IRspectrum of the yellow precipitate shows a strong absorption (much like that of a quinone) around 1680 cm-1. Proposestructures for the two productsarrow_forward
- VII. 1-bromo-3-methyl-2-butene undergoes nucleophilic substitution reaction in both ethanol and sodium ethoxide/DMSO mixture. (1) Please write all organic substitution products for each of the two reactions, if two products are formed in a reaction, assign the major product, assuming that the reaction is under kinetic control (2) What is the most likely mechanism for each reaction? (giving the name of mechanism is sufficient).arrow_forward(d) Illustrate and briefly explain the mechanism of reaction II.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) 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
- 11.; (a) Similar to alkanes, hydrogen gas can undergo radical bromination according to the reaction below. Propose a chain-reaction mechanism for this reaction, including an initiation step, propagation steps, and two plausible termination steps. The homolytic bond dissociation energy for Br-Br is 46 kcal·mole', for H-Br is 88 kcal'mole and for H-H is 104 kcal'mole'. hv H-H + Br-Br 2 H-Br (b) Calculate the overall AH for the above propagation steps (show all work).arrow_forward(a) Given and Scara were given a task of synthesising (2-methylprop-1- enyl)cyclohexane 2 (A potential TB drug). After a brief discussion with each other, Given proposed Method A to synthesise 2 from cyclohexanecarbaldehyde 1 while Scara proposed Method B that started from hydroxymethylcyclohexane 3. When designing a synthetic route for drug molecule, you have to make sure the synthetic process is as efficient as possible (e.g. few synthetic steps, mostly making one product and more). THF A Ph Ph Ph B 3 1. PCC 2. isopropyl magnesium vromide 3. H₂SO4 100 °C OH Method B is not preferred synthetic route due to the number of steps involve (3 steps vs 1 step for Method A). What else is making method A unfavorable synthetic method? Use curly arrows to explain this effect. (Ctrl) -arrow_forward7. (1) What would you expect to be the order of reactivity from the following pyridine Derivatives towards electrophilic substitution (i.e. list from most reactive to the least reactive) and why? (ii) Can you also indicate which position would be favoured for such substitution in each of those and why? O,N `NO2arrow_forward
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