H₂C H₂C ممل CH3 CH3 Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 07 →XT :OH 2 CH₂OH HCI catalyst CH3 H₂CO OCH3 сн он H₂C H3C HO: :OCH3 CH3 46

H₂C H₂C ممل CH3 CH3 Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 07 →XT :OH 2 CH₂OH HCI catalyst CH3 H₂CO OCH3 сн он H₂C H3C HO: :OCH3 CH3 46

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Section21.SE: Something Extra

Problem 75AP: One frequently used method for preparing methyl esters is by reaction of carboxylic acids with...

See similar textbooks

Similar questions

H3C- H3C. OCH 3 H3CO CH3 H Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions NA 2 CH₂OH HCI catalyst CH3 HỘ H3CQ H3C- H3CO CH3 H3C. OCH3 CH3 H₂O*: 45
H3C OH OH H+ CH3 Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CIX 10-4 H₂O CH3 H₂O CH3
Fill in thhe blanks with the appropriate chemical compound for the following reactions: 1-methylcyclohexanol + phosphoric acid catalyst + heat --> + 2-methylcyclohexanol + phosphoric acid catalyst + heat --> 3-methylcyclohexane 3-methylcyclohexene methylenecyclohexane| 2-methylcyclohexene 1-methylcyclohexene 1-methylcyclohexane Next pag ge MacBook Air
Give the chemical name of the products A and B in the following sequence of reactions: CH;CH,OH CH;CH,NH2 A heat
H₂SO4, H₂O Choose the enol(s) that can be formed from the following oxymercration reaction. OH ОН OH HgSO4 ОН
Give the main organic product for the following reaction: CH2OH OH H3O* CH3CH2CH2OH OH OH
acetone H3C, HO H3C OH The product of the following reaction is: A OH H3C OH C D OB
What is the major organic product obtained from the following reaction? A HQ, D OH C.
Claisen condensation between diethyl phthalate and ethyl acetate followed by saponifi- cation, acidification, and decarboxylation forms a diketone, C,H,O,. COOEt 1. EtO Na+ HCI, H,O B NaOH, H,O + CH3COOEt C,H,O2 2. НС, Н,О heat heat COOEt Diethyl phthalate Ethyl acetate Propose structural formulas for compounds A and B and the diketone.
HO, но. Chrysanthemic acid Chrysanthemyl alcohol OH H20 TsO. DMSO Chrysanthemyl tosylate Artemesia alcohol Yomogi alcohol Chrysanthemic acid occurs as a mixture of esters in flowers of the chrysanthemum (pyrethrum) family. Reduction of chrysanthemic acid to its alcohol, followed by conversion of the alcohol to its tosylate, gives chrysanthemyl tosylate. Solvolysis of the tosylate gives a mixture of artemesia and yomogi alcohols. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. Arrow-pushing Instructions HO+ :OH :A H-A
Give the major organic product(s) of the following reaction. 1) NABH4 ? 2) H3o+
What is the major organic product obtained from the following reaction? H HC A) 1 B) 2 HO H₂SO4 C) 3 OH 2 سل، ز. مل D) 4 OH