Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
expand_more
expand_more
format_list_bulleted
Question
Chapter 20, Problem 33P
Interpretation Introduction
Interpretation: Among the given esters, the more reactive ester in nucleophilic acyl substitution is to be predicted.
Concept introduction: Carboxylic acid derivatives undergo nucleophilic acyl substitutions on the carbonyl groups. The first step is the attack of nucleophile on the carbonyl carbon and then loss of leaving group. The better the leaving group, the higher is the reactivity of carbonyl compounds.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Consider carbonyl compounds A–E drawn below. (a) Rank A–E in order of increasing stability. (b) Rank A–E in order of increasing amount of hydrate formed when treated with aqueous acid. (c) Which compound is most reactive in nucleophilic addition?
Draw a stepwise mechanism for the attached Friedel–Crafts acylation
What product is formed when A is treated with Grubbs catalyst underhigh-dilution conditions? This reaction was a key step in the synthesis ofstemoamide, the naturally occurring amide described in the opening paragraph.
Chapter 20 Solutions
Organic Chemistry (6th Edition)
Ch. 20.1 - Prob. 1PCh. 20.2 - Draw the three possible resonance structures for...Ch. 20.2 - Prob. 3PCh. 20.3 - Give an IUPAC or common name for each compound. a....Ch. 20.3 - Problem 22.5 Draw the structure corresponding to...Ch. 20.4 - Problem 22.6 Explain why the boiling point of is...Ch. 20.7 - Prob. 11PCh. 20.7 - Prob. 12PCh. 20.8 - Prob. 13PCh. 20.9 - Problem 22.16 Draw the products of each reaction.
...
Ch. 20.9 - Prob. 17PCh. 20.9 - Problem 22.18 Draw a stepwise mechanism for the...Ch. 20.9 - Prob. 19PCh. 20.10 - Problem 22.20 Fenofibrate is a...Ch. 20.10 - Problem 22.21 What product is formed when the...Ch. 20 - Prob. 33PCh. 20 - 22.40 Give the IUPAC or common name for each...Ch. 20 - 22.41 Give the structure corresponding to each...Ch. 20 - Prob. 36PCh. 20 - 22.43 Explain why is a stronger acid and a weaker...Ch. 20 - (a) Propose an explanation for the difference in...Ch. 20 - Draw the product formed when phenylacetic acid is...Ch. 20 - Prob. 42PCh. 20 - Prob. 43PCh. 20 - Prob. 44PCh. 20 - Prob. 45PCh. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - 22.64 What carboxylic acid and alcohol are needed...Ch. 20 - Problem 22.65 Devise a synthesis of each compound...Ch. 20 - 22.70 What polyester or poly amide can be prepared...Ch. 20 - 22.71 What two monomers are needed to prepare each...
Knowledge Booster
Similar questions
- Look at the imide, the nitrogen analog of an anhydride below: a) For a neutral imide, will the carbonyl carbon be more (easier to attack) orless (harder to attack) electrophilic than the C of a neutral anhydride? b) If the imide is hydrolyzed under acidic conditions, which atom, one of theoxygens or the nitrogen, will be protonated? Explain your answer.arrow_forwardHow does an SN1 reaction mechanism form answers A and C?arrow_forwardDraw a stepwise mechanism that illustrates how both products are formed in the following reaction.arrow_forward
- Identify A in the following reaction scheme, and draw a stepwise mechanism for the conversion of A to the furan B.arrow_forwardDraw a stepwise mechanism for the attached reaction, which involves two Friedel–Crafts reactions. B was an intermediate in the synthesis of the antidepressant sertralinearrow_forwardDraw a stepwise mechanism for the sulfonation of an alkyl benzene such as A to form a substituted benzenesulfonic acid B. Treatment of B with base forms a sodium salt C that can be used as a synthetic detergent to clean away dirtarrow_forward
- Draw a stepwise mechanism for the sulfonation of an alkyl benzene such as A to form asubstituted benzenesulfonic acid B. Treatment of B with base forms a sodium salt C that canbe used as a synthetic detergent to clean away dirt.arrow_forward(a) Draw two different halo ketones that can form A by an intramolecular alkylation reaction. (b) How can A be synthesized by an acetoacetic ester synthesis?arrow_forwardDraw synthetic schemes for a to darrow_forward
- Acid-catalyzed dehydration of β-hydroxy carbonyl compounds occurs by the mechanism. With this in mind, draw a stepwise mechanism for the following reaction.arrow_forward(a) Draw two different halo ketones that can form A by an intramolecularalkylation reaction. (b) How can A be synthesized by an acetoacetic estersynthesis?arrow_forward(a) Draw a stepwise mechanism for the conversion of A to B. (b) What product would be formed if C was exposed to similar reaction conditions?arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning