Draw structure of a tertiary alcohol, give its correct name and the show the REACTION MECHANISM for the formation of an alkyl halide from this alcohol. (7) HINT: - The reaction is SN1, it takes place through 3 STEPS and TWO carbocations forms as intermediates. - The reaction was carried in the presence of an acid and in the presence of halide ions, and not at elevated temperature. - Halide ions are good nucleophiles (they are much stronger nucleophiles than water), and since halide ions are present in high concentration, most of the carbocations react with an electron pair of a halide ion to form a more stable species, the alkyl halide product. - OH group is a poor leaving group, thus the alcohol gets protonated first.

Draw structure of a tertiary alcohol, give its correct name and the show the REACTION MECHANISM for the formation of an alkyl halide from this alcohol. (7) HINT: - The reaction is SN1, it takes place through 3 STEPS and TWO carbocations forms as intermediates. - The reaction was carried in the presence of an acid and in the presence of halide ions, and not at elevated temperature. - Halide ions are good nucleophiles (they are much stronger nucleophiles than water), and since halide ions are present in high concentration, most of the carbocations react with an electron pair of a halide ion to form a more stable species, the alkyl halide product. - OH group is a poor leaving group, thus the alcohol gets protonated first.

Pushing Electrons

4th Edition

ISBN:9781133951889

Author:Weeks, Daniel P.

Publisher:Weeks, Daniel P.

Chapter6: Valence Electrons (redux)

Section: Chapter Questions

Problem 6EQ

See similar textbooks

Similar questions

When the hypochlorite oxidation is performed on secondary alcohols such as 1-phenolethanol, the product of the reaction is benzoate ion and trichloromethane if an excess of hypochlorite is used in the absence of a buffer to keep the pH below 10. Explain the formation of these products (Hint: what reaction do the products remind you of?) Provide a complete mechanism?
Give a chemical reaction not found in the table below for distinguishing between D and E. Reagents, reaction conditions and visible changes should be stated.
Friedel-Crafts Alkylation, based on substituted benzene reaction, including reactivity based on electron donating and withdrawing group and also discuss the possible positions (Ortho, Meta and Para) for the new group. Explain if there is polysubstitution occurs. Keeping the reaction mixture in the ice bath and adding the reagent slowly by continuously stirring is the key point of success.
c. Is the predicted trend for alkyl chlorides the same as or different than the predicted trend for alkyl bromides? Briefly elaborate. d. The type of alkyl bromide is the same in tubes 4 and 7 but one is acyclic and the other cyclic. Should there be any difference in the predicted rate of SN2 reaction of these alkyl bromides? Briefly elaborate. 2a. Describe the predicted trend between the rate at which the SN2 reaction occurs and the leaving group for each of the following entries: 1 and 2 3 and 4 5 and 6 b. What general conclusion can be made concerning the rate at which the SN2 reaction occurs and the leaving group? 3. Alkyl iodides were not used in this part of the experiment. Why? Explain.
For the base-catalysed hydrolysis of 3-bromo-3-methylhexane (i.e. reaction with the nucleophile OH-): State whether the reaction is likely to proceed by an SN1 or SN2 mechanism, and explain why give the likely rate law and explain why
Imagine 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.
Illustrate the reaction mechanism for the ethylation of p-cyclopropylphenol (other reactants: AlCI3 and ethylchloride). Refer to Friedel-Craft Alkylation mechanism as your guide in doing this mechanism. Show ALL partial charges in the EACH structure using BLUE ink. Arrows should be written using RED ink.
Given the sequence of reactions shown below assume the reactions are stoichiometric fill in the reagents needed for steps A B and C and explain what happens in each step of the reactions, by also name
What is the strongest IMF in pure 2-octanone? I know it is a ketone and has some polarity due to this, but the carbon chain so long, I wonder if london dispersion forces are stronger?
] The reaction of 2-bromopropane and sodium ethoxide in ethanol reacts 6.7 times faster than 2-bromo-1-deuteriopropane under the same conditions. Explain what mechanism this data is consistent with, and why
1. Esters can be synthesized from the nucleophilic substitution reaction of anhydrides and alcohol in the presence of a base give a complete mechanism and the final product for the reaction below 2. using appropriate illustrations, explain what is meant by the tetrahedral transition state( also indicate the geometry for the starting material and product).
what would a detailed step-by-step mechanism be for a reaction between bromine and trans-stilbene if the solvent, ethanol, is a stronger nucleophile than the bromide ions?