Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 11, Problem 39P
D. N. Kursanov, a Russian chemist, proved that the bond that is broken in the hydroxide-ion-promoted hydrolysis of an ester is the acyl C—O bond, rather than the alkyl C—O bond, by studying the hydrolysis of the following ester under basic conditions:
- a. What product contained the 18O label?
- b. What product would have contained the 18O label if the alkyl C—O bond had broken?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
14. The smell of acetaldehyde appears when heated with potassium permanganate and the addition of dilute sulfuric acid:
A) Ascorbic acid
B) Calcium lactate
C) Gamma-aminobutyric acid
D) Chlorotane
4. Draw a chemical reaction scheme that includes an arrow - pushing mechanism for each of the following reactions: a.
Protonation of p-acetyl aniline by HCI followed by deprotonation with NaOH b. Deprotonation of benzoic acid by
NaOH followed by protonation with HCI
3-Methylbutanoic acid, produced by bacteria from leucine, is a component of wine flavor and is responsible for foot odor.Which
alkylating agent(s) should be used for the malonic ester synthesis of 3-methylbutanoic acid?
O
O
O
A Ethyl bromide and methyl bromide
B 2-Bromopropane and methyl bromide
с
D
2-Bromopropane
Methyl bromide, methyl bromide, methyl bromide
E Methyl bromide, malonyl bromide
Chapter 11 Solutions
Essential Organic Chemistry, Global Edition
Ch. 11.1 - The aromas of many flowers and fruits are due to...Ch. 11.1 - Name the following compounds:Ch. 11.1 - Prob. 3PCh. 11.2 - Prob. 4PCh. 11.2 - Prob. 5PCh. 11.4 - a. What is the product of the reaction of acetyl...Ch. 11.4 - Prob. 7PCh. 11.5 - Using the pKa values listed in Table 11.1, predict...Ch. 11.6 - Starting with acetyl chloride, what neutral...Ch. 11.6 - Prob. 10P
Ch. 11.7 - Prob. 11PCh. 11.8 - Prob. 13PCh. 11.8 - Using the mechanism for the acidcatalyzed...Ch. 11.8 - Prob. 15PCh. 11.8 - Prob. 16PCh. 11.8 - Prob. 17PCh. 11.9 - Prob. 18PCh. 11.10 - Show how each of the following esters could be...Ch. 11.11 - Which of the following reactions would lead to the...Ch. 11.12 - Prob. 22PCh. 11.12 - Prob. 23PCh. 11.13 - Prob. 24PCh. 11.13 - Prob. 25PCh. 11.14 - Prob. 26PCh. 11.14 - Prob. 27PCh. 11.14 - Prob. 28PCh. 11.15 - Prob. 29PCh. 11.15 - How would you synthesize the following compounds...Ch. 11 - Write a structure for each of the following a. N,N...Ch. 11 - Prob. 32PCh. 11 - Which ester is more reactive, methyl acetate or...Ch. 11 - What products would be formed from the reaction of...Ch. 11 - What products would be obtained from the following...Ch. 11 - Prob. 36PCh. 11 - a. Which compound would you expect to have a...Ch. 11 - a. List the following esters in order of...Ch. 11 - D. N. Kursanov, a Russian chemist, proved that the...Ch. 11 - Prob. 40PCh. 11 - Using an alcohol for one method and an alkyl...Ch. 11 - Prob. 42PCh. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Show how the following compounds could be prepared...Ch. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Prob. 53P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- During the synthesis of the antiasthmatic drug montelukast (Singulair), a silyl ether protecting group is used to mask the reactivity of an OH group. The silyl group chosen is the tert-butyldimethylsilyl (TBS) group. Draw the product of the following transformation, assuming the TBS-Cl reagent reacts only once with the starting material. Briefly explain your answer.arrow_forward10. Which of the following compounds does not undergo hydrolysis with either acid or basic catalysis: 00 H3Cca CH3CH2ČNH2 CHICOCHCH3 CH3COCH2CH2CH3 B. CHICCH2CH3 F. None of the molecules shown undergoes hydrolysis.arrow_forwardWhich reagents are best used to produce 4-methyl-2-pentanol from a ketone? a. amins and trace acid, followed separetely H2/PD/C b. sodium cyanide followed by HCl c. sodium borohydridd followed by acidic work up d. hydrogen cyanide followed by HCl e. none of the abovearrow_forward
- ČOEt 1. EtO-Na+ OEt 3. NAOH, H,O, heat EtO 4. HCI, heat 2-Carbethoxy- 4-Butanolactone 4-butanolactone (y-Butyrolactone) Show how the scheme for formation of 4-butanolactone can be used to synthesize lactones (a) and (b), each of which has a peach odor and is used in per- fumery. As sources of carbon atoms for these syntheses, use diethyl malonate, ethylene oxide, 1-bromoheptane, and 1-nonene. (b) (racemic) (racemic)arrow_forward7. Only one of the following carboxylic acids can be made via a malonic ester synthesis. Which one is it? Ph A Ph. OH OH Ph OH OH B C D OH Earrow_forwardNH2 HO, H. Atenolol Tenormin® Below is a two-step reaction sequence. What are the steps in the synthesis? `NH2 -NH2 `NH2 base OH OH O The phenolate reacts with the epoxide preferentially over the alkyl halide at the less sterically hindered position. Then, the sterically hindered amine attacks the alkyl chloride. O The phenolate reacts with the epoxide preferentially over the alkyl halide at the more sterically hindered position. Then, the sterically hindered amine attacks the alkyl chloride.arrow_forward
- Fill in the appropriate reagents for the following reaction:arrow_forwardThe reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, doesnot work with primary alcohols. a. Propose a mechanism for the Ritter reaction.b. Why does the Ritter reaction not work with primary alcohols?c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?arrow_forwardIn the reaction of a nitrile with a Grignard reagent, there are two steps: a) nucleophilic addition of the Grignard to form an imine ion and b) hydrolysis of the imine to form a ketone. Draw the intermediate and the final product in this reaction. Ignore inorganic byproducts. 1. CH₂MgBr 2. H3O* Draw Imine Ion Intermediate 1. H30¹ 2. Neutralizing work-up aarrow_forward
- Which alkyl halides were used in the acetoacetic ester synthesis to make the substituted ketone below? You may choose more than one answer. CH3BR CH3CH2CH2Br СНЗСН2Br O (CH3)2CHB.arrow_forward4. For the following reaction schemes, fill in the appropriate reagents and starting materials you would use to transform the acetoacetic ester and acetone into nabumetone, an NSAID drug used for arthritis and joint pain. Write the correct reagents/reactants next to the number of steps for each transformation. 1. OEt 2. MeO nabumetone 3. 1. Meo 2. nabumetonearrow_forwardThe reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, does not work with primary alcohols. a. Propose a mechanism for the Ritter reaction. b. Why does the Ritter reaction not work with primary alcohols? c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Enzymes - Effect of cofactors on enzyme; Author: Tutorials Point (India) Ltd;https://www.youtube.com/watch?v=AkAbIwxyUs4;License: Standard YouTube License, CC-BY
Enzyme Catalysis Part-I; Author: NPTEL-NOC IITM;https://www.youtube.com/watch?v=aZE740JWZuQ;License: Standard Youtube License