CAREY: ORGANIC CHEMISTRY
10th Edition
ISBN: 9781260364002
Author: VALUE EDITION
Publisher: MCG CUSTOM
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 23, Problem 18P
Interpretation Introduction
Interpretation: The compound A in the given synthesis of the analogs of anthracycline antibiotics is to be identified.
Concept introduction:
The reaction that involves the rearrangement of the esters of phenol into a hydroxyl aryl
The relocation of the phenol ester acyl group to the aryl ring takes place in this type of reaction.
Expert Solution & Answer

Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Assign all integrated peaks
- Consider the data in the Table below to answer the following questions:
Acidities of Substituted Benzoic and Acetic Acids
pk,s at 25C
Y-CH COOH
Y
Y - CH₂COOH
meta
para
H
4.75
4.19
4.19
2.47
3.64
3.55
3.57
4.09
4.46
CN
OCH 3
A. Draw the structure of the strongest acid in the table above.
B. Explain why cyanoacetic acid and methoxyacetic acid are more acidic than their correspondingly
substituted benzoic acid counterparts.
Draw the curved arrow mechanism for this reaction starting with 2-propanol in sulfuric acid. Show all nonzero formal charges and all
nonbonded electrons in each step. Species not involved in a particular step do not need to be included in that step, and resonance forms
do not need to be shown. Note that the alcohol is in much higher concentration than H₂O in this reaction.
H
Chapter 23 Solutions
CAREY: ORGANIC CHEMISTRY
Ch. 23.1 - Prob. 1PCh. 23.3 - Problem 23.2 One of the hydroxybenzoic acids is...Ch. 23.4 - Prob. 3PCh. 23.5 - Prob. 4PCh. 23.6 - Problem 23.5 The compound shown was required for...Ch. 23.8 - Prob. 6PCh. 23.8 - Prob. 7PCh. 23.9 - Prob. 8PCh. 23.9 - Prob. 9PCh. 23.10 - Prob. 10P
Ch. 23.12 - Prob. 11PCh. 23 - The IUPAC rules permit the use of common names for...Ch. 23 - Prob. 13PCh. 23 - Prob. 14PCh. 23 - Prob. 15PCh. 23 - Prob. 16PCh. 23 - Prob. 17PCh. 23 - Prob. 18PCh. 23 - Prob. 19PCh. 23 - Prob. 20PCh. 23 - Prob. 21PCh. 23 - Prob. 22PCh. 23 - Prob. 23PCh. 23 - Prob. 24PCh. 23 - Prob. 25PCh. 23 - Prob. 26PCh. 23 - Choose the reaction in each of the following pairs...Ch. 23 - Pentafluorophenol is readily prepared by heating...Ch. 23 - Prob. 29PCh. 23 - Treatment of p-hydroxybenzoic acid with aqueous...Ch. 23 - Prob. 31PCh. 23 - Prob. 32PCh. 23 - Treatment of 2,4,6-tri-tert-butylphenol with...Ch. 23 - Prob. 34PCh. 23 - Prob. 35PCh. 23 - Prob. 36DSPCh. 23 - Prob. 37DSPCh. 23 - Prob. 38DSPCh. 23 - Prob. 39DSP
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
- Provide reactions showing the following conversions: * see imagearrow_forward. Draw structures corresponding to each of the following names or Provide IUPAC names for each of the ollowing structures [for 4 ONLY]. A. 2-propylpentanoic acid. B. m-chlorobenzoic acid. D. C. O O HOC(CH2)3COH glutaricadd OH OH H3C CH3 C=C H COOH salicylicadd tiglicadd CH₂C=N Joe Marrow_forward. Provide structure(s) for the starting material(s), reagent(s) or the major organic product(s) of each of the ollowing reactions or sequences of reactions. Show all relevant stereochemistry [five only] A. O B. OET CH3 1. LIAIH, ether 2 H₂O O (CH3)2CH-C-CI + 0 0 ether (CH3)2CH-C-O-C-CH3 CH3 C. 0 OH HO CH3 ° Clarrow_forward
- How would you prepare each of the following compounds using either an acetoacetic ester synthesis or a alonic ester synthesis? Show all intermediate structures and all reagents.[Three only] A. B. COOH OH C. D. 0 H2C CHCH2CH2CCH3arrow_forwardFats and greases have mostly aliphatic regions which are hydrophobic. Provide a schematic of howsoaps/detergents remove fats and grease from the soiled material. * see imagearrow_forwardWhat chemical has the common name "lye"? Pick one of the 3 esters and show the hydrolysis mechanism to make a carboxylic acid. The organic “R” should be used to limit the redrawing time of the entire molecule. * see imagearrow_forward
- Provide the products for each reaction. There are two and they are not related. *see imagearrow_forwardd. a phenylal Give the major organic product(s) of each of the following reactions or sequences of reactions. Show all levant stereochemistry. [three only] 0 A. B. CH3 Bra CH3COOH OH 1. Br₂, PBrz 2 H₂O 12arrow_forward2arrow_forward
- Show how the following conversions might be accomplished. Show all reagents and all intermediate ructures. More than one step may be required [2 ONLY]: A. B. ° C. OH 0 OH 0arrow_forwardA 20.3 mL sample of 0.263 M triethylamine, (C2H5)3N, is titrated with 0.252 M hydrochloric acid. (1) At the titration midpoint, the pH is . (2) At the equivalence point, the pH is .arrow_forwardd. 3,4,5-trimethoxybenzoyl chloride . What is the order of decreasing reactivity towards nucleophilic acyl substitution for the arboxylic acid derivatives? (most reactive first) A. B. 0 0 O 0 0 H3C-C-O-C-CH3 H3C-C-N(CH3)2 H3C-C-OCH 3 (CH3)2CH-C-OCH3 I || ။ IV a. I, II, III, IV b. I, III, IV, II C. II, IV, III, I d. II, I, III, IV 0 0 0 0 0 R-C-O C-R R-C-NH2 R-C OR R-C-CI a. I, III, II, IV | 11 III IV b. II, III, I, IV c. III, II, I, IV d. IV, I, III, IIarrow_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

NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY