You have learned how secondary alkyl halides are usually good substrates forSN1 and SN2 reactions. Chlorocyclopropane, however, will not react under eitherof the following conditions: (a) sodium methoxide in methanol or (b) methanol.Explain non-verbally why the two conversions fail.

SN2 reaction required strong nucleophile while SN1 reaction required weak nucleophile..

Answered: You have learned how secondary alkyl…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.44P

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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) 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
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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-methylpropene
(c)Show step by step how to synthesize methoxybenzene from benzene.
When exactly 1 mole of methane is mixed with exactly 1 mole of chlorine and light is shone on the mixture, a chlorination reaction occurs. The products are found to contain substantial amounts of di-, tri-, and tetrachloromethane, as well as unreacted methane. Explain how a mixture is formed from this stoichiometric mixture of reactants, and propose mechanisms for the formation of these compounds from chloromethane.
The structure below is the cyclic ether (epoxide), butene oxide: (1) CH3CH₂ -CH₂ butene oxide How could this compound be prepared from but-1-ene? Explain why butene oxide is much more reactive than its isomer, tetrahydrofuran, which is also a cyclic ether: H₂C-CH₂ H₂C CH₂ tetrahydrofuran Illustrate how butene oxide reacts with ammonia, showing details of the mechanism leading to the final product, C4H11 NO.
Ethane reacts with chlorine (Cl2) in the presence of ultra-violet (UV) light, to produce 1-chloropropane (CH3CH2Cl) and hydrogen bromide (HCl). As shown in the equation below.CH3CH3+ Cl2→ CH3CH2Cl+ HClDescribe the reaction mechanism of the reaction between ethane and chlorine to produce 1-chloroethane. The description should be detailed and must include the type of bond fission that takes place. You may sketch and insert suitable diagrams to aid your description if you wish.
A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br. (a) Draw the resonance forms of the three possible allylic free radical intermediates.
(a) In an acid-catalyzed hydration, one of the following 10 carbon alkynes is expected to produce a single hydration product? Select the correct alkyne and draw the structure of the hydration product that is formed from this alkyne. (I) 2-decyne; (II) 3-decyne; (III) 4-decyne; (IV) 5-decyne; (V) none of these will give a single hydration product. (b) The reaction shown below gives Compound X as the major product. The mass spectrum of X is shown. Br2, H20 Compound X 100 - MS-IW-5644 80 60 40 - 20 - 20 40 60 80 100 120 140 160 180 200 220 m/z Considering the reactions of alkynes and the MS data, de duce which of following structures corresponds to X: Br Br HO, IV V I II II Support your answer with a reaction mechanism for fomation of X and identification of relevant peaks in the mass spectrum. 12 Relative Intensity
The relative rates of reaction of ethane, toluene, and ethylbenzene with bromine atoms have been measured. The most reactive hydrocarbon undergoes hydrogen atom abstraction a million times faster than does the least reactive one. Arrange these hydrocarbons order of decreasing reactivity.
The reaction of 1-bromopropane and sodium hydroxide in ethanol occurs by an SN2mechanism. What happens to the rate of this reaction under the following conditions?(a) The concentration of NaOH is doubled.(b) The concentrations of both NaOH and 1-bromopropane are doubled.(c) The volume of the solution in which the reaction is carried out is doubled.
Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev’s rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak…

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You have learned how secondary alkyl halides are usually good substrates for SN1 and SN2 reactions. Chlorocyclopropane, however, will not react under either of the following conditions: (a) sodium methoxide in methanol or (b) methanol. Explain non-verbally why the two conversions fail.