Part III: Mechanism of acid-catalyzed ester hydrolysisConsider the following six-step reaction when answering the questions below::0:R--CH₂+Step 1: Ester protonation10:H₂O4. The first step in this reaction mechanism uses the acid catalyst to protonate the ester.a. Which site on the ester is the most basic and therefore most likely to gain the proton? To helpanswer this question draw the conjugate acid that would result from protonation of either siteand explain which conjugate acid is more stable.

Part III: Mechanism of acid-catalyzed ester hydrolysis Step 1: Ester protonationThe first step in…

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Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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For each reaction: a) draw out the Lewis structures for the reactants given b) identify the electrophile (meaning a Lewis acid) and nucleophile (meaning a Lewis base) c) draw the curved arrows that show the direction of electron flow to form the product d) draw the structure of the product(s) you would expect. 3. CH3BR + NH3 4. CH3CH2B + CH3NH2
Given the structures of cocaine (right) and its free base (left) below: a. Would you expect K for the cocaine to be greater or less than 1.0? Explain. b. Would K for the free base be higher or lower than for cocaine? Explain. c. To favor the equilibrium towards the free base, would you make the aqueous solution acidic or basic? Explain. (Hint: think of Le Chatelier’s principle).
4. The pk, of vanillin is about 9, which is much more acidic than a normal alcohol. Draw a reaction showing the deprotonation of vanillin with NaOH, and then draw six resonance structures of the conjugate base. Draw the hybrid structure and clearly indicate how the negative charge is distributed in the compound.
Answer the following questions for the reaction scheme below: OH e :CEN HIC N cyanide hydrogen cyanide phenol pka <= 10.0 pka = 3.46 a. The equilibrium favors the [Select] b. This reaction is best described as a(n) [Select] c. The strongest acid in the reaction is the [Select] [Select] d. The nucleophile in the forward reaction is e. The electrophile in the reverse reaction is [Select] phenolate %. ✓ reaction. 15 <
Write out a chemical equation (draw bond-line structure) for the reaction between p-bromoaniline with hydrochloric acid. Show the mechanism using curved arrows AND identify the acid and base in the reactants.
Determine the steps to proceed the following synthesis.
What will be the carboxylate ion produced when 3-methylhexanoic acid dissociates in water? + H2O 2 ? + H2O ОН O hexanoate ion O 3-methylhexanoic acid ion O 3-methylhexanoate ion O 3-methylhexanoic ion O hydroxide ion
Draw the organic product of the Bronsted acid-base reaction. Include all lone pairs and charges as appropriate. Ignore any counterions. H3O+ Select to Draw H Z: H
Arrange these phenolic compounds in order of increasing acidity. Least acidic Most acidic Answer Bank НО -N+ Но CI Но HO
8
QUESTION 16 Select the most acidic proton in the molecule shown below. H H 4 O A. 2 O B. 4 O C. 3 O D. 1 QUESTION 17 All of the following are characteristics of a Wittig reaction except: O A. It is an èfficient method for the synthesis of alkenes. O B. It involves the reaction of a phosphonium ylide with a carbonyl compounds. O C. It involves an Sn2 reaction between a carbanion and an aldehyde or ketone. O D. It results in the exclusive formation of trans C=C double bonds. QUESTION 18 Click Save and Submit to save and submit. Click Save All Answers to save all answers. P Type here to search Esc F1 F2 F3 F4 F5 F6 F7 F8 F9 * %23 24 4. 7 8 CO # 3
State which acid is the strongest acid and which is the weakest acid? Briefly explain your answer. 3,4-dimethylhexanoic acid b. 3,3-dichlorohexanoic acid 3-bromo-4-iodohexanoic acid d. 3-fluoro-4-chlorohexanoic acid

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