Concept explainers
Interpretation:
The classification of the formation of industrial preparation of methyl bromide from methanol by reaction with hydrogen bromide is to be done. The stepwise mechanism is to be written.
Concept introduction:
The reaction of methyl and primary alcohols with hydrogen halide mostly proceeds through
The reaction of tertiary alcohol with hydrogen halide proceeds through
The
The
Formation of carbocation is the rate determining step in
The nucleophile (halide ion) attacks on the electrophilic carbon from opposite side of hydroxyl group (i.e. backside attack) in
The position of leaving group in reactant and that of nucleophile in the product are same in case of
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Solutions Manual for Organic Chemistry
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- Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.arrow_forwardUnder milder temperatures than what is needed for dehydration, strong acids catalyze the self-condensation of 1-propyl alcohol to give di-n-propyl ether. The mechanism differs from that of today's reaction in that the protonated alcohol undergoes an Sn2 rather than an Sn1 reaction. Write the mechanism for the acid catalyzed condensation of ethyl alcohol to give diethyl ether. Make sure the mechanism includes protonation, Sn2, and deprotonation.arrow_forward3b)Give the mechanisms for the following transformations:arrow_forward
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- 8a)Provide mechanisms for the following reactions:arrow_forward1. Methylene cyclohexane, on treatment with strong acid, isomerises to yield methyl cyclohexene. Propose a mechanism by which the reaction might occur.arrow_forwardNeopentyl alcohol, (CH3)3CCH2OH, reacts with concentrated HBr to give 2-bromo2-methylbutane, a rearranged product. Propose a mechanism for the formation of thisproduct.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning