Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 24, Problem 24.57P
Interpretation Introduction
Interpretation: The stepwise mechanism for the conversion of A to B is to be drawn.
Concept introduction: The Aldol condensation reaction that takes place within the same molecule in presence of strong base is known as intramolecular aldol reactions. This reaction takes place within the dicarbonyl compounds in which one carbonyl group forms the enolate that acts as a nucleophile and reacts with second carbonyl group which acts as electrophile.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
When A is treated with aqueous −OH, the major product is compound B, which undergoes ester hydrolysis and decarboxylation to form C. Draw a stepwise mechanism for the conversion of A to B.
When A is treated with aqueous −OH, the major product is compound B, which undergoes ester hydrolysis and decarboxylation to form C. Draw a stepwise mechanism for the conversion of A to B.
When A is treated with aqueous −OH, the major product is compound B, which undergoes ester hydrolysis and decarboxylation to form C. Draw a stepwise mechanism for the conversion of A to B.
Chapter 24 Solutions
Organic Chemistry
Ch. 24 - Prob. 24.1PCh. 24 - Prob. 24.2PCh. 24 - Problem 24.3
What unsaturated carbonyl compound is...Ch. 24 - Prob. 24.4PCh. 24 - Prob. 24.5PCh. 24 - Prob. 24.6PCh. 24 - Problem 24.7
Draw the products formed in each...Ch. 24 - Problem 24.8
Draw the products formed in the...Ch. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Prob. 24.15PCh. 24 - Problem 24.16
What ester is formed when each...Ch. 24 - Prob. 24.17PCh. 24 - Prob. 24.18PCh. 24 -
Draw the products of each reaction.
a. b.
Ch. 24 - Problem 24.20
Two steps in a synthesis of the...Ch. 24 - Prob. 24.21PCh. 24 - Problem 24.22
Which of the following compounds can...Ch. 24 - Prob. 24.23PCh. 24 - Problem 24.24
What starting materials are needed...Ch. 24 - Problem 24.25
Draw the products when each pair of...Ch. 24 - Prob. 24.26PCh. 24 - Problem 24.27
What starting materials are needed...Ch. 24 - Prob. 24.28PCh. 24 - 24.29 What steps are needed to convert A to B?
Ch. 24 - Prob. 24.30PCh. 24 - 24.31 Draw the product formed in each directed...Ch. 24 - Prob. 24.32PCh. 24 - 24.33 What starting materials are needed to...Ch. 24 - Prob. 24.34PCh. 24 - Prob. 24.35PCh. 24 - 24.36 Identify the structures of C and D in the...Ch. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - 24.39 Draw the product formed from a Claisen...Ch. 24 - Prob. 24.40PCh. 24 - 24.41 Even though B contains three ester groups, a...Ch. 24 - Prob. 24.42PCh. 24 - Prob. 24.43PCh. 24 - 24.44 Vetivone is isolated from vetiver, a...Ch. 24 - Draw the product of each Robinson annulation from...Ch. 24 - Prob. 24.46PCh. 24 - 24.47 Draw the organic products formed in each...Ch. 24 - 24.48 Fill in the lettered reagents needed for...Ch. 24 - Prob. 24.49PCh. 24 - Prob. 24.50PCh. 24 - Prob. 24.51PCh. 24 - 24.52 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.53PCh. 24 - Prob. 24.54PCh. 24 - Prob. 24.55PCh. 24 - Prob. 24.56PCh. 24 - Prob. 24.57PCh. 24 - Prob. 24.58PCh. 24 - Prob. 24.59PCh. 24 - 24.60 Devise a synthesis of each compound from the...Ch. 24 - 24.61 Devise a synthesis of each compound from...Ch. 24 - 24.62 Devise a synthesis of each compound from ,...Ch. 24 - Prob. 24.63PCh. 24 - Prob. 24.64PCh. 24 - 24.65 Answer the following questions about...Ch. 24 - Prob. 24.66PCh. 24 - Prob. 24.67PCh. 24 - Prob. 24.68PCh. 24 - 24.69 Devise a stepwise mechanism for the...Ch. 24 - 24.70 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.71PCh. 24 - Prob. 24.72PCh. 24 - Prob. 24.73P
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
- One step in the synthesis of the antihistamine fexofenadine involves acid-catalyzed hydration of the triple bond in A. Draw a stepwise mechanism for this reaction and explain why only ketone B is formed.arrow_forwardDraw the product(s) formed when A is treated with each reagent. (a) NaBH4, CH3OH (b) [1] LiAlH4; [2] H2O (c) CH3CH2MgBr; [2] H2Oarrow_forwardDraw a stepwise mechanism for the following reaction, one step in the synthesis of the cholesterol-lowering drug pitavastatin, marketed in Japan as a calcium salt under the name Livalo.arrow_forward
- Even though B contains three ester groups, a single Dieckmann product results when B is treated with NaOCH3 in CH3OH, followed by H3O+. Draw the structure and explain why it is the only product formed.arrow_forwardDraw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with each reagent. With some reagents, no reaction occurs. NaHCO3arrow_forwardAn allylic alcohol contains an OH group on a carbon atom adjacent to aC—C double bond. Treatment of allylic alcohol A with HCl forms amixture of two allylic chlorides, B and C. Draw a stepwise mechanismthat illustrates how both products are formed.arrow_forward
- Even though B contains three ester groups, a single Dieckmann product results when B is treated with NaOCH3 in CH3OH, followed by H3O+. Draw the structure and explain why it is the only product formed.arrow_forwardThe analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate alkylation in one step, what reagents are needed to convert A to naproxen? Draw the structure of each intermediate. Explain why a racemic product is formed.arrow_forwardDraw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with following reagent. With some reagents, no reaction occurs. NH3 (1 equiv)arrow_forward
- Draw a stepwise mechanism for the following reaction in (a) aacid-catalyzed and (b) base-catalyzed hydration.arrow_forwardWhat product is formed when a solution of A to B is treated with mild base? This reaction is the first step in the synthesis of rosuvastatin (sold as a calcium salt under the trade name Crestor), a drug used to treat patients with high cholesterol.arrow_forwardDraw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with following reagent. With some reagents, no reaction occurs. [1] NaOH; [2] CH3COClarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
