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 11PP
Interpretation Introduction
Interpretation: The allylic monobromo substitution products for the given compounds, the most stable isomeric product based on the double bond, and the resonance hybrid(s) for allylic radicals that are formed in each are to be discussed.
Concept introduction:
Molecules that have one unpaired electron are called free radicals.
A
Allylic bromination take place in the presence of NBS and peroxide or light. NBS is a good reagent for allylic bromination.
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(a) What monobromo allylic substitution products would result from reaction of each of PRACTICE P
the following compounds with NBS in the presence of peroxides and/or light? (b) In the
case of isomeric products for any reaction, which would you predict to be the most stable
based on the double bond in the product? (c) Draw the resonance hybrid(s) for the allylic
radical that would be involved in each reaction.
(i)
(ii)
V
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(iii)
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Can you help me with question (C)
PRACTICE PROBLEM 8.20
Specify the alkene and reagents needed to synthesize each of the following diols.
OH
HO-
(a)
(b)
(c)
HO.
н он
HO
(racemic)
(racemic)
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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- 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_forward9.19. 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 CH₂CH3arrow_forwardGive explanation of the correct option and explanation of the incorrect options.arrow_forward
- 46arrow_forwardDrawn below are the structures of (+)-menthol and (-)-menthol. These are stereoisomers of one another. They have identical physical properties are indiscernible by most laboratory techniques (e.g. melting point, boiling point, IR spectroscopy), except they interact with polarized light differently (hence the +/- designation). Curiously, they can be perceived differently by humans by our sense of smell. (a) Make a model of the structures or draw them both and describe how they are related geometrically. (b) Why is it that these nearly physically identical compounds can be discerned by our sense of smell? OH HO (+)-menthol (-)-mentholarrow_forwardBoth questions related to each other. Need solution for both with explanationarrow_forward
- 2. Isomerization of alkenes can be achieved through conjugate addition of nucleophiles. Examine the reaction below and answer the questions that follow: i) ii) iv) bigg Starting Alkene Alkene Product Give the chemical structure of the Alkene Product that is formed (NB: Show and label the geometry of the Alkene Product). Explain why geometry given in i) above is preferred. What is likely to be the geometry of the Starting Alkene? Give the full mechanism through which the isomerization is likely to occur.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_forwardDiscuss the hybridization, aromaticity, and stability of the following organic intermediate. Also, arrange them in the increasing order of stability. CHarrow_forward
- (d) Consider the following catalyzed and non-catalyzed pathways of a substitution reaction of bromoethane. Draw an energy diagram for each of the following reactions (label all axes and include reactants, intermediates (if any) and products). CH3CH₂Br + HO CH³CH₂OH + B (non-catalyzed) ное CH3CH₂Br + CH3CH₂OH + 1 (catalyzed) CH3CH₂ + Brarrow_forwardGive explain in shortarrow_forward• PRACTICE PROBLEM 8.12 Treating a hindered alkene such as 2-methyl-2-butene with BH3:THE leads to the for- mation of a dialkylborane instead of a trialkylborane. When 2 mol of 2-methyl-2-butene is added to 1 mol of BH3, the product formed is bis(3-methyl-2-butyl)borane, nicknamed in reagent "disiamylborane." Write its structure. Bis(3-methyl-2-butyl)borane is a useful certain syntheses that require a sterically hindered borane. (The name “disiamyl" comes from "disecondary-iso-amyl," a completely unsystematic and unacceptable name. The name "amyl" is an old common name for a five-carbon alkyl group.) donbyarrow_forward
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