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 5PP
Interpretation Introduction
Interpretation:
The chain reaction mechanism for the formation of
Concept introduction:
Radical halogenation is the reaction in which hydrogen atoms of
At normal temperature and pressure, chlorine and methane do not react with each other. The reaction is initiated by light or heat. When exposed to light,
The reaction that is initiated by light is more efficient because a very small amount of light photons allows a large number of products to be formed.
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Can you help me with question (C)
3-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 methoxide
When tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether. (a) What happens to the rate if the concentration of tert-butyl bromide is tripled and the concentration of ethanol is doubled?
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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- 3-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) dimethyl sulfoxide (DMSO) is used in place of methanol (b) methanol is used by itself without sodium methoxide (c) 1-chloro-2,2,-dimethylpropane is used in place of 3-chloro-2-methylpropenearrow_forward3-Chloro-1-butene reacts with sodium ethoxide in ethanol to produce 3-ethoxy-1- butene. The reaction is second order, first order in 3-chloro-1-butene, and first order in sodium ethoxide. 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.arrow_forwardAnswer the following questions regarding the nucleophilic substitution reaction shown below: CH3CH2CH2-Br + I- ------> CH3CH2CH2I + Br- (a) Write the rate law for this reaction assuming that it is a one step reaction that is first order in each of the reactants. (b) Holding the concentration of the iodide ion constant, what change would be observed in the rate if the concentration of the n- propyl bromide was tripled? (b) Assume that this is an exothermic reaction, draw the energy profile and identify the location of the transition state. (c) Draw the transition state for this reaction. (d) What change is observed for the entropy of the system during this reaction? (e) Show the likely mechanism of this reaction using the proper curved arrowsarrow_forward
- (a) Give the names of reagents and conditions for each of the reactions I and IIarrow_forwardImagine that phenol (“hydroxybenzene”) and nitrobenzene are reacted (in separate beakers) with a hot solution containing both concentrated sulfuric acid and concentrated nitric acid. A) In analyzing the products, you discover that the substitution pattern resulting from the reaction with phenol differs from the reaction with nitrobenzene. Explain this difference in substitution patterns using one or more judiciously selected reaction mechanisms or portions of mechanisms.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
- Bromine reacts with alkenes in methanol according to the equation (see image 1). When this reaction was carried out with 4-tert-butylcyclohexene, only one isomer was formed with the molecular formula C12H23BrO (80% yield) a) Which of the following is the structure more reasonable for this compound? (see image 2) b) Explain your reasoning through a corresponding mechanismarrow_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_forwardElimination of HBr from 2-bromobutane affords a mixture of 1-butene and 2-butene. With sodium ethoxide as base, 2-butene constitutes 81% of the alkene products, but with potassium tert-butoxide, 2-butene constitutes only 67% of the alkene products. Offer an explanation for this difference.arrow_forward
- 7.) Carbocations are high energy intermediates in organic synthesis that are open-shelled carbon atoms. In the reaction below (a) we see that carbocations are also excellent Lewis acids, readily accepting a water molecule to form the product isopropanol. Given this, explain why when reaction (b) was set up, there were two regioisomeric products formed? Please draw a Lewis acid base reaction mechanism with arrows to justify your answer. H20 H OH H3CO CH3 H3C CH3 a.) carbocation Product open-shell H H20 Н. ОН b.) H3C H3C H3C and HO, ČH3 ČH3 ČH3arrow_forward( plz with detail explanation )arrow_forwardthe question is from Solomon's organic chemistry 11th edition book.arrow_forward
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