The acid-catalyzed hydrolysis of an ester converts anester into a carboxylic acid. Although there are two Oatoms that can be protonated, the first step in themechanism is believed to be protonation of the oxygenin the C=0 group. Based on charge stability, why is itfavorable to protonate that oxygen? Hint: Draw out theproducts of each protonation.+ HоHO,НОCarboxylicacidEsterAlcohol

Esters are the organic compounds having to oxygen atoms (RCOOR), one is linked to carbon by a double…

Answered: The acid-catalyzed hydrolysis of an…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 64AP: The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold...

See similar textbooks

Similar questions

Arrange these compounds in order of increasing boiling point (values in °C are -42, -24, 78, and 118). (a) CH,CH,OH (b) CH,OCH, (c) CH,CH,CH, (d) CH,COOH
A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.(a) Draw the resonance forms of a carboxylic acid that is protonated on the hydroxyoxygen atom.(b) Compare the resonance forms with those given previously for an acid protonated on thecarbonyl oxygen atom
Rank the following compounds in their correct order of acidity. 1=Most acidic and 4=least acidic.
(i) Identify the acidic proton(s) for each of the following carbonyl compounds: O O ( CHỊCH, CÁCH, BỊ CHỊCHỊCH, CÁCH, (2) || (3) CHy-O-C-CH,-C-O-CH, (4) CH,-C-CH, (ii) Rank the compounds (in part (i) above) in the order of increasing or decreasing acidity by using the symbol "" in your answer.
но HO но он The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic than acetic acid (CH3CO0H, pKa 4.74). (a) Show the fou r different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid. (b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic. (c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.
Complete each acid-base reaction and predict whether the position of equilibrium lies toward the left or toward the right. (a) CH3CCH+CH3CH2ONa+CH3CH3OH (b) CH3CCCH2CH2OH+Na+NH2NH3(l)
The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold Helminthosporium sativum, involves the following base treatment of a keto tosylate. What kind of reaction is occurring? How would you complete the synthesis?
Rank the following acids in decreasing acidity. Explain your answer CH2ClCOOH, CHCl2COOH, CH3COOH
1. c) Indicate the most acidic hydrogen in each of the following molecules. 요 CH3COCH 3 X° (CH₂CH₂)₂NLi O || CH3CNHCH3 CH,CH,ONa 4 d) Arrange the following bases in order of increasing basicity, starting from the weakest base on the left to the strongest base on the right. O (CH3)3CCCH3 (CH3), COK CHỊCH Li (CH₂CH₂),N
(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects. PPha NaOCH,CH3 HO- isotretinoin HO A Br X Y
Predict the products of the following acid-base reactions. If the equilibrium would not result in the formation of appreciable amounts of products, you should so indicate. In each case label the stronger acid, the stronger base, the weaker acid, and the weaker base: (a) CH3CH=CH2 + NANH2 (d) CH3C=C: + CH;CH2OH → (e) CH3C=C:- + NH¾CI – | (b) CH;C=CH + NaNH2 (c) CH3CH2CH3 + NANH2 → | HAS
From 1 being the least acidic and 4 being the most acidic, arrange the following organic compounds in terms of increasing acidity

SEE MORE QUESTIONS

Recommended textbooks for you

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:

Cengage Learning

SEE MORE TEXTBOOKS