ORGANIC CHEMISTRY-ETEXT REG ACCESS
12th Edition
ISBN: 9781119308362
Author: Solomons
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.
Higher
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(3) HI does not undergo free radical addition with 1-butene, even in the presence
of a peroxide. Please provide an explanation by analyzing the propagation
steps if the same radical reaction occurred with HI. Besides the bond
dissociation enthalpies in the appendix, the following approximate bond
dissociate enthalpies might be useful to you:
~310 kJ/mol
The component of C=C
CH3CH₂CH₂CH₂-Br
CH3CH₂CH₂CH2-I
-290 kJ/mol (C-Br bond)
~235 kJ/mol (C-I bond)
The relative reactivity of the 1°: 2°: 3° hydrogens of (CH3)3CCH2CH3 in free radical chlorination is 1: 3.8: 5.0. Provide the structure of each monochlorination product, and estimate the relative amount of each in the mixture of monochlorinated products.
The compound below is treated with N-bromosuccinimide (NBS) in
the presence of light.
Draw both resonance structures for the radical produced by reaction
of the compound with a bromine atom. Assume reaction occurs only
at the weakest C-H bond.
Chapter 10 Solutions
ORGANIC CHEMISTRY-ETEXT REG ACCESS
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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- 8. (a) Benzene derivatives exhibit medium to strong absorption in UV-region. Explain why aniline and phenoxide ion have strong UV-absorptions.arrow_forwardFree‑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_forward
- Draw an orbital correlation diagram for the suprafacial-suprafacial reaction of an allyl species with an olefin to give the corresponding cyclopentyl species, and establish whether the reaction is allowed or forbidden for the cation, anion, and radical. = 0. 5 Draw the orbital correlation diagram for the addition of ozone to ethylene to give a five-membered ring ozonide. Is the reaction allowed or forbidden? 6. Predict the product of the following reaction. The reaction involves an intermediate (I) which sets the stereochemistry in the product. What is this intermediate, and what is the stereochemistry of the product? (Hint: The first reaction involves a pericyclic C-C bond cleavage.) Ph I N Heat H₂CO₂C CO₂CH3 H_CO,C-C=C-CO,CH, P diene interconversion of Eq. 15.18.arrow_forward10.47 (•) Suggest a method for synthesizing the following alkynes using an alkyne and an alkyl halide. [There are two correct answers for each product.] (a) Pharrow_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_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_forwardPractice Problem 10.32 For each of the products shown in the following reaction, propose a mechanism that explains its formation: Step 1 ? NBS hv Step 2 Get help answering Molecular Drawing questions. Draw single barbed curved arrows and the products formed in the initiation step for this reaction. (Include lone pairs in your answer.) Edit LINK TO TEXT Br + + Br LINK TO VIDEO Attempts: 0 of 3 used SAVE FOR LATER SUBMIT ANSWERarrow_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
- 2. (a) (b) OUTLINE, using suitable mechanisms, how each of the following conversions is achieved. In each case, you should indicate the reagents to be used and show ALL intermediate compounds. Each arrow may represent one or more than one step. CH3CH₂Br (C6H5)3P CHCH3 H CH3 ——-||- H- (C₂H₂)₂N- H H CH,CH,CHO -CHO H₂C CH3 CHCH3arrow_forwardShow how free-radical halogenation might be used to synthesize the followingcompounds. In each case, explain why we expect to get a single major product.(a) 1-chloro-2,2-dimethylpropane (neopentyl chloride)(b) 2-bromo-2-methylbutanearrow_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
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