Interpretation: The result of
Concept introduction:
Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.
Intramolecular catalysis: A catalysis where catalyst is a part of the molecule that undergoes the reaction promotes the reaction in a species.
Intramolecular nucleophilic catalysis: A catalysis where catalyst is a part of the molecule that undergoes the reaction promotes the reaction in a species by acting as a nucleophile.
Intramolecular general-base catalysis: A catalysis where catalyst is a part of the molecule that undergoes the reaction promotes the reaction in a species by completely removing a proton during the slow step in a reaction.
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EBK ORGANIC CHEMISTRY
- Propanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4. Draw a diagram to show the mechanism of the reaction of either propanal or propanone with acidified potassium cyanide.arrow_forwarddescribe how steric and electronic effects influence the postion of equilibrium when the electrophilic center of an aldehyde or ketone is under nucleophilic attack.arrow_forwardH NH₂ ཡིནྣཾ ༥ ཨ ཨནྡྷ༥ ༠ ཨི་ཝཱ, ཙ ཨ་ར༩ H NH3+ the acidity of the amine ion drives the reaction to shift toward the conjugate base of the carboxylic acid product. the resulting carboxylic acid ion is a weaker base than an acetate ion. O aldehydes are more reactive toward nucleophiles than ketones. Onucleophilic attack occurs preferentially at the less hindered carbon of the formyl group.arrow_forward
- -Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the -hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the -hydroxyketone or aldehyde. Write a mechanism for the oxidation of this -hydroxyaldehyde by HIO4.arrow_forwardThe base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.arrow_forwardClaisen condensation between diethyl phthalate and ethyl acetate followed by saponification, acidification, and decarboxylation forms a diketone, C9H6O2. Propose structural formulas for compounds A and B and the diketone.arrow_forward
- Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forward1-Explain oxidative and reductive Ozonolysis 2- Give the sequence of the relative reactivities of carboxylic acid derivatives. Explain why acyl chloride can be converted into ester but ester cannot be converted into acyl chloride 3- Write the product when ester of propionic acid, propionyl chloride and propanal reacts with excess of methyl magnesium bromidearrow_forwardComplete the statements by providing the reagents necessary to complete each step of the synthesis. Ketone reacted with CO₂H and then yielded a derivative, which was treated with 1) (i) C6H5MgBr (ii) H3O+ 2) (i) DIBAL-H (ii). H3O+ 3) Sia2BH,H202, NaOH 4) CH2N2 (diazamethane) CO₂C2H5 5) PCC (an oxidant) 6) H2SO4, H2O, heat 7) HgSO4/ H2SO4 8) C₂H5OH, H3O*, heat TABLE OF REAGENTS to form an unsaturated carboxylic acid, treatment with to yield unsaturated aldehyde as the final product. CHO MacBook Air 9) C6H5 CH2 P(C6H5)3; NaOH 10) PCC (an oxidant) 11) NaCN, H₂SO4 12) PhCH2CHO, H3O*arrow_forward
- Give an example of an ester that is used to activate alcohols towards nucleophilic substitution and beta-elimination reactionsarrow_forwardIn the acid-catalyzed dehydration of 2-methyl-1-propanol, what carbocation would be formed if a hydride shift accompanied cleavage of the carbon–oxygen bond in the alkyloxonium ion? What ion would be formed as a result of a methyl shift? Which pathway do you think will predominate, a hydride shift or a methyl shift?arrow_forwardKetones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example: R1 ОН 1. НС—с: Na* R2 R1 R2 2. Нзо" HC Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes preferentially from the Si face of the carbonyl group. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it. CH3 CHarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning