Haloalkanes undergo substitution reactions, sometimes taking place via an mechanism, sometimes via an SN2 mechanism. In a reaction where it is not known which specific mechanism is involved, describe how a combination of kinetic and stereochemical evidence could be used to determine which mechanism is taking place. Secondary haloalkanes are capable of reacting by both mechanisms, though the one which takes place depends on the precise reaction conditions. Briefly suggest how factors such as the strength of the nucleophile and the nature of the solvent may influence whether the reaction mechanism is SN1 or SN2

Haloalkanes undergo substitution reactions, sometimes taking place via an mechanism, sometimes via an SN2 mechanism. In a reaction where it is not known which specific mechanism is involved, describe how a combination of kinetic and stereochemical evidence could be used to determine which mechanism is taking place. Secondary haloalkanes are capable of reacting by both mechanisms, though the one which takes place depends on the precise reaction conditions. Briefly suggest how factors such as the strength of the nucleophile and the nature of the solvent may influence whether the reaction mechanism is SN1 or SN2

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

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.43P

See similar textbooks

Similar questions

Describe the reaction mechanism for the hydrolysis of 2-bromo-2-methylpropane [CH3C(CH3)2Br] with aqueous hydroxide ions (OH-).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
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.
Alkyl halides can be reduced to alkanes by a radical reaction with tributyltin hydride, (C4H9)3SnH, in the presence of light (hv). Propose a radical chain mechanism by which the reaction might occur. The initiation step is the light-induced homolytic cleavage of the Sn-H bond to yield a tributyltin radical.
As has been demonstrated in the text, when the starting alkene has CH, as its terminal group, the Heck reaction is highly stereoselective for formation of the E isomer. Here, the benzene ring is abbreviated C,H,-. Show how the mechanism proposed in the text allows you to account for this stereoselectivity. Pd(OAc), 2 Ph P CH,=CH-COCH, + C,H,Br CH, OCH3 (CH;CH2)3N
write the free radical monosubtitution mechanism for the bromination of ethane to produce bromoethane
The following alcohols react with HBr to afford an alkyl bromide. Based on their structures, indicate if the reaction mechanism is likely to be Sn1 or Sn2
A) Provide the reagent and reaction mechanism to show how the reactants and products in the following reaction can interconvert B) under what conditions would the reaction I) favour reactants, II) favour the products and III) why?
Provide the mechanisms for chlorination of toluene which include the initiation, propagation and termination steps
Please provide mechanisms for these reactions
Describe the principle and mechanism behind the catalytic hydrogenation of alkenes using a heterogeneous catalyst. Explain the factors that influence the reaction rate and selectivity in this process.
(a) (i) 3-Methyl-2-butanol will react with sulphuric acid to give two isomeric alkenes in 3:1 proportions.(i) Write down the structures for these alkenes and assign appropriate systematic names to them. (ii) Name the most abundant isomer. (iii) Write down detailed mechanism for the formation of a minor product.
Following is an equation for hydroperoxidation of cumene. light + O2 for HOO- Cumene Cumene hydroperoxide Propose a radical chain mechanism for this reaction. Assume that initiation is by an unspecified radical, R.