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a)
Interpretation:
How to carry out the selective transformation of a ketoaldehyde to ketoalcohol is to be shown.
Concept introduction:
Both
To show:
How to carry out the selective transformation of a ketoaldehyde to ketoalcohol.
b)
Interpretation:
How to carry out the selective transformation of a diketone to an aldol is to be shown.
Concept introduction:
Both aldehyde and keto groups are reduced by LiAlH4. In order to selectively reduce one keto group, the other keto group is first protected by converting it into an acetal. The protected
To show:
How to carry out the selective transformation of a diketone to an aldol.
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Chapter 19 Solutions
Organic Chemistry
- A key step in a synthesis of the antimalarial drug quinine involves an intramolecular nucleophilic substitution that converts A to B. Draw the structure of B and give the reagents needed to convert B to quinine.arrow_forwardThe following molecule undergoes an intramolecular reaction in the presence of pyrro- lidinium acetate, the protonated form of pyrrolidine. Draw the product of this reaction, assuming that a dehydration reaction takes place. Me Me Но N: 'N' AcO Ме pyrrolidinium acetate Me Me Mearrow_forwardHow does propane synthesized from propanone? Show its mechanism.arrow_forward
- Draw the structures of the initially formed enol tautomers in the reactions of propyne and dicyclohexylethyne with dicyclohexylborane followed by NaOHNaOH and H2O2H2O2arrow_forward9) How would you carry out the following transformation? More than one step may be required, write the reactions. H3C CH 3 H3C ? H3C CH3 OH H H3C H "ОН 10) How would you synthesize the following compound from cyclohexanone? More than one step may be required, write the reactions. CH 3arrow_forwardPropose a mechanism for conversion of 4-hydroxybenzaldehyde to A.arrow_forward
- Given this analysis, propose a synthesis for dinocap from phenol and 1-octene.arrow_forwardhow to synthesize 2-phenylclohexanone from cyclohexanone?arrow_forwardProvide the reagents necessary to complete the following reactions. More than one step may be necessary, if so number separate steps.arrow_forward
- Ph- OC XT :OH₂ Primary amines add to aldehydes and ketones to give imines. Imines are formed in a reversible, acid-catalyzed process that begins with nucleophilic addition of the primary amine to the carbonyl group, followed by transfer of the proton to yield a neutral carbinolamine. Protonation of the hydroxyl group converts it into a good leaving group and an E1-like loss of water yields an iminium ion. Deprotonation yields the product imine and regenerates the acid catalyst. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions NHOH CH3 CH3 NH₂OH OH HN I Ph CH3 OH H₂O CH3 заarrow_forward2 H3C H3C H C→XT OH H3C The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ß-hydroxy carbonyl compound. base :0: OH H H Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instruct ns H3C heat OH H3C :0: H + H₂O Harrow_forwardNAC↔X™ Ph Ph OH Acid chlorides react with Grignard reagents to yield tertiary alcohols, two equivalents of Grignard reagent are required. The first equivalent reacts in a typical nucleophilic acyl substitution reaction to give a ketone. This ketone, however, is itself reactive in the Grignard reaction. Thus, the second equivalent adds to the ketone carbonyl carbon. Subsequent protonation yields the tertiary alcohol. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Ph :0: 1. 2 eq. CH3MgBr 2. H3O+ CH3 H3C CH3 H3C-MgBr Ph O: MgBr -CH3 CH3arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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