Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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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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9.19. Analyze the results of the studies of intramolecular electrophilic substitution
that are described below. Write mechanisms for each of the cyclizations and
comment on the relation between ring size and the outcome of cyclization.
(a)
CH 3
CH3
(CH₂
(CH₂)3CHCH3
CI
CH3NO2
0 °C, 4h
CH3 CH3
CH₂CH3
(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.
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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- 8. (a) Benzene derivatives exhibit medium to strong absorption in UV-region. Explain why aniline and phenoxide ion have strong UV-absorptions.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_forward2. (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_forward
- (d) Illustrate and briefly explain the mechanism of reaction II.arrow_forward7.(a) Write a detailed mechanism (using arrows) to explain only two of the following: Br Br Br, uv CCI4 Br HBr ROORarrow_forwardPropose a second chain propagation step. Remember that a characteristic of chain propagation steps is that they add to the observed reactionarrow_forward
- 4. (3) For each of the following reactions, fill in the missing reagents from the list provided for the formation of the product shown. Sequential steps, if necessary, should be numbered. Reagents may be used more than once. Reagent List: Lit NaH NaNH2 Na+ H,C-S-CI HBr PBr3 H20 Br2 Li-CH3 но NaOH Br-CH3 KBr (HOAC) (pyridine) (LDA) (MSCI) но Br. Br 5. (5) In reaction A, the product was determined to be racemic (both enantiomers were formed). (a) Propose a curved arrow mechanism for reaction A that accounts for this observation. (b) Predict the product for reaction B where conditions now use a different chloride source. b) H-CI но CI 1. LICI 2. HCI reaction A reaction Barrow_forwardA very large number of Diels-Alder reactions are recorded in the chemical literature, many of which involve relatively complicated dienes, dienophiles, or both. Predict the constitution of the Diels-Alder adduct that is expected to form from the combination of diene and dienophile below. Draw the structure of the predicted product, including relevant stereochemistry when applicable. If applicable, use the Bicyclic Stamp tool and guide points to draw each structure. Click and drag to start drawing a structure.arrow_forwardA very large number of Diels-Alder reactions are recorded in the chemical literature, many of which involve relatively complicated dienes, dienophiles, or both. Predict the constitution of the Diels-Alder adduct that is expected to form from the combination of diene and dienophile below. Draw the structure of the predicted product, including relevant stereochemistry when applicable. If applicable, use the Bicyclic Stamp tool and guide points to draw each structure. NH + NC CN X NC CN Click and drag to start drawing a structure.arrow_forward
- This is not B or Darrow_forward4. 3-chloro-1-butene reacts with sodium ethoxide in ethanol to produce 3- ethyoxy-1-butene. In the absence of sodium ethoxide, 3-chloro-1-butene reacts with ethanol to produce both 3-ethoxy-1-butene and 1-ethoxy-2-butene. Explain these results. Be sure to include mechanisms and structures in your explanation. H. CH2=CH-C-CH3 ÓCH,CH3 GH,-CH=C-CH3 ÓCH,CH, 3-Ethoxy-1-butene 1-Ethoxy-2-butenearrow_forward7carrow_forward
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