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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Organic Chemistry
- The 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_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_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_forward
- Each of the following reactions has been carried out under conditions such that disubstitution or trisubstitution occurred. Identify the principal organic product in each case. (a) Nitration of p-chlorobenzoic acid (dinitration) (b) Bromination of aniline (tribromination) (c) Bromination of o-aminoacetophenone (dibromination) (d) Bromination of p-nitrophenol (dibromination) (e) Reaction of biphenyl with tert-butyl chloride and iron(III) chloride (dialkylation) (f) Sulfonation of phenol (disulfonation)arrow_forwardIn the Grignard Reaction experiment what would the reaction mechanism be if the reactants are Magnesium, 2-bromopropane, 4-benzaldehyde, phosphoric acid and diethyl ether, resulting in a product of 1-(4-methoxyphenyl)-2-methylpropan-1-olarrow_forwardExplain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism. During the development of the optimized procedure for the experiment, it was found out that compound 1b can also be produced from the same set of starting materials. Propose a detailed reaction mechanism for the formation of 1b. Explain your answer. What factor/s may drive the formation of 1b over 1a?arrow_forward
- Treatment of pentanedioic (glutaric) anhydride with ammonia at elevated temperature leads to a compound of molecular formula C5H7NO2. What is the structure of this product? [Hint: You need to think about the reactivity not only of acid anhydrides but also of amides and carboxylic acids]arrow_forwardTo synthesize trans-cinnamic acid from benzaldehyde (PhCHO) and acetic anhydride (Ac2O) under basic, refluxing conditions to exemplify the Perkin condensation. 1. Draw the complete chemical reaction to be carried out. 2. Provide a complete arrow-pushing mechanism for the synthesis of trans-cinnamic acid. 3. Briefly describe the role of water, Na2CO3, and HCl in the isolation of the product. Draw the structure of the product at basic pH (after Na2CO3 addition) and at acidic pH (after HCl addition).arrow_forward(a) Arrange the following compounds in an increasing order of their indicated property :(i) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength)(ii) CH3CH2CH (Br) COOH, CH3CH (Br) CH2COOH,(CH3)2CHCOOH, CH3CH2CH2COOH (acid strength)(b) How would you bring about the following conversions :(i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde(iii) Bromobenzene to 1-phenylethanolarrow_forward
- Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide.What is the leaving group in your proposed mechanism? Would this be a suitableleaving group for an SN2 reaction?arrow_forwardWhat is the role of an acid catalyst in nucleophilic addition of aldehydes and ketone?arrow_forwardOn synthesis of esters via nucleophilic acyl substitution: How is excess alcohol eliminated from the crude product? Write the chemical equation involved in the reaction between the excess acid and NaHCO3. Given this, briefly explain why NaHCO3 is preferred over NaOH for the neutralization of excess acid.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning