a)
Interpretation:
Given that the final step in the hydration of an
Concept introduction:
The enol picks up a proton from H3O+ using the unshared pair of electrons on oxygen and the π electrons in the double bond to yield a carbocation. The carbocation ion then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.
To propose:
A mechanism for the tautomerization reaction shown.
b)
Interpretation:
Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.
Concept introduction:
The enol picks up a proton from H3O+ using the unshared pair of electrons on oxygen and the π electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.
To propose:
A mechanism for the tautomerization reaction shown.
c)
Interpretation:
Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.
Concept introduction:
The enol picks up a proton from H3O+ using the unshared pair of electrons on oxygen and the π electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.
To propose:
A mechanism for the tautomerization reaction shown.
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Chapter 9 Solutions
Organic Chemistry
- A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:arrow_forwardComplete the following reaction and provide the detailed mechanism NaOH NaOH +arrow_forwardGive detailed Solution with explanation needed..don't give Handwritten answerarrow_forward
- Complete the following reaction, which may take place in several steps, by supplying all reagents and conditions necessary. Include all important intermediates - mechanisms are not required.arrow_forwardThe following isomers react separately with sodium hydroxide to give different products with the formulas shown. HO. .CI Но NaOH NaOH C3H1,02 (a) Draw the structure of each product. (b) Draw the mechanism that accounts for the formation of each of those products. (c) Explain why the isomeric reactants lead to different products.arrow_forwardGive handwritten answer Provide mechanism?arrow_forward
- The following elimination reaction results in a mixture of products. Explain why the major products obtained in larger quantities than the minor products. Use chemical structures as necessary to justify your answer.arrow_forwardDevise concise syntheses for the following transformations. Clearly show the reagent and product foreach step.arrow_forwardGive detailed mechanism Solution with explanation needed..don't give Handwritten answerarrow_forward
- Complete the Reaction below and provide the following (i) a detailed stepwise mechanism to account for the product(s), including all steps involved (ii) Clearly show all the resonance structures and intermediates formed leading to the product. OH acetic anhydridearrow_forwardGive detailed Solution with explanation neededarrow_forwardGive detailed Solution with explanation neededarrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning