Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
5th Edition
ISBN: 9781260170405
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Question
Chapter 26, Problem 26.54P
Interpretation Introduction
Interpretation: The stepwise mechanism for the conversion of
Concept introduction: Suzuki reaction is a type of substitution reaction. It involves the palladium coupling between organic halide with organoborane in the presence of base. It is a stereospecific reaction.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
16.48 D is an intermediate in the synthesis of rosiglitazone (trade name
Avandia), a drug used to treat type 2 diabetes. Suggest two different
methods to prepare the ether in D by substitution reactions.
CHO
D
omoss
rosiglitazone
H
Propose a synthesis of molecule B from molecule A. For each step, indicate the necessary reagents.
A key step in the synthesis of β-vetivone, a major constituent of vetiver, a perennial grass found in tropical and subtropical regions of the world, involved the reaction of compound A and dihalide B with two equivalents of LDA to form C. Draw a stepwise mechanism for this reaction. β-Vetivone contains a spiro ring system—that is, two rings that share a single carbon atom.
Chapter 26 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
Ch. 26 - Prob. 26.1PCh. 26 - Prob. 26.2PCh. 26 - Prob. 26.3PCh. 26 - Prob. 26.4PCh. 26 - Prob. 26.5PCh. 26 - Prob. 26.6PCh. 26 - Prob. 26.7PCh. 26 - Problem 26.8
What starting materials are needed to...Ch. 26 - Prob. 26.9PCh. 26 - Problem 26.10
What reagents are needed to convert...
Ch. 26 - Problem 26.11
What product is formed when each...Ch. 26 - Prob. 26.12PCh. 26 - Problem 26.13
Draw the products formed when each...Ch. 26 - Problem 26.14
What products are formed when ...Ch. 26 - Problem 26.15
Draw the product formed from...Ch. 26 -
What product is formed by ring-closing metathesis...Ch. 26 - Problem 26.17
What starting material is needed to...Ch. 26 - 26.18 In addition to organic halides, alkyl...Ch. 26 - 26.19 What product is formed by ring-closing...Ch. 26 - 26.20 Draw the products formed in each...Ch. 26 - What organic halide is needed to convert lithium...Ch. 26 - 26.22 How can you convert ethynylcyclohexane to...Ch. 26 - 26.23 What compound is needed to convert styrene...Ch. 26 - 26.24 What steps are needed to convert to octane...Ch. 26 - Prob. 26.25PCh. 26 - Prob. 26.26PCh. 26 - 26.27 Draw the products (including stereoisomers)...Ch. 26 - 26.28 Treatment of cyclohexene with and forms...Ch. 26 - Prob. 26.29PCh. 26 - 26.30 What starting material is needed to prepare...Ch. 26 - Prob. 26.31PCh. 26 - Prob. 26.32PCh. 26 - When certain cycloalkenes are used in metathesis...Ch. 26 - 26.34 Draw the products formed in each reaction.
...Ch. 26 - Prob. 26.35PCh. 26 - Draw a stepwise mechanism for the following...Ch. 26 - Sulfur ylides, like the phosphorus ylides of...Ch. 26 - Although diazomethane is often not a useful...Ch. 26 - Prob. 26.39PCh. 26 - Prob. 26.40PCh. 26 - Prob. 26.41PCh. 26 - Prob. 26.42PCh. 26 - 26.43 Devise a synthesis of each compound using a...Ch. 26 - 26.44 Devise a synthesis of each compound from...Ch. 26 - 26.45 Devise a synthesis of each compound from...Ch. 26 - 26.46 Devise a synthesis of each substituted...Ch. 26 - Biaryls, compounds containing two aromatic rings...Ch. 26 - Prob. 26.48PCh. 26 - 26.49 Draw the product formed from the...Ch. 26 - Prob. 26.50PCh. 26 - 26.51 Devise a synthesis of each of the following...Ch. 26 - Prob. 26.52PCh. 26 - 26.53 The following conversion, carried out in the...Ch. 26 - Prob. 26.54PCh. 26 - 26.55 Dimethyl cyclopropanes can be prepared by...Ch. 26 - Prob. 26.56P
Knowledge Booster
Similar questions
- Rank compound A, B, and C in the order of increasing stability.arrow_forwardIdentify the missing reagents a-f in the following scheme:arrow_forwardNicotinic acid, more commonly named niacin, is one of the B vitamins. Show how nicotinic acid can be converted to (a) ethyl nicotinate and then to (b) nicotinamide.arrow_forward
- (a) What is the major alkene formed when A is dehydrated with H2SO4? (b) What is the major alkene formed when A is treated with POCl3 and pyridine? Explain why the major product is different in these reactions.arrow_forwardUsing ethynylcyclohexane as a starting material and any other needed reagents, how can the following compounds be synthesized?arrow_forwardProblem 4.20 Show the alkyne and alkyl halide from which the following products can be obtained. Where two routes look feasible, list both. (c) CH3 CH3CHCH2CH2C=CH (a) (b) CH3CH2CH2C=CCH3 CH3 CH3CHC=CCH3arrow_forward
- One step in the synthesis of sitaglipitin (Problem 17.14, a drug used to treat type 2 diabetes) involves reaction of the mixed anhydride A with B to form C. Draw a stepwise mechanism for this reaction.arrow_forwardSlow addition of organolithium reagent A to B afforded C, anintermediate in the synthesis of the chapter-opening molecule,resiniferatoxin. Draw a stepwise mechanism for this process.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? Write the structure of each intermediate. Explain why a racemic product is formed.arrow_forward
- What product is formed when each compound undergoes thermal electrocyclic ring opening or ring closure? Label each process as conrotatory or disrotatory and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds. а. b.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? Write the structure of each intermediate. Explain why a racemic product is formed.arrow_forwardExplain, with reference to the mechanism, why addition of one equivalent of HCl to diene A forms only two products of electrophilic addition, even though four constitutional isomers are possible.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
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT