Suzuki-Miyaura coupling is a reliable method to make biaryl compounds (Ar-Ar'). The reaction is tolerant of a wide range of functional groups. What are some transformations that can be done to the acetyl group (CH3C-0) after the following Suzuki coupling? For example, Grignard reactions, Wittig reactions, imine/enamine formation, aldol condensations, reduction..... The world is big; keep exploring. OH Br B Pd(PPh3)4 NaOAc THF-H₂O + HO CH3 CH3

Suzuki-Miyaura coupling is a reliable method to make biaryl compounds (Ar-Ar'). The reaction is tolerant of a wide range of functional groups. What are some transformations that can be done to the acetyl group (CH3C-0) after the following Suzuki coupling? For example, Grignard reactions, Wittig reactions, imine/enamine formation, aldol condensations, reduction..... The world is big; keep exploring. OH Br B Pd(PPh3)4 NaOAc THF-H₂O + HO CH3 CH3

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...

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Suzuki-Miyaura coupling is a reliable method to make biaryl compounds (Ar-Ar'). The reaction is tolerant of a wide range of functional groups. What are some transformations that can be done to the acetyl group (CH3C-0) after the following Suzuki coupling? For example, Grignard reactions, Wittig reactions, imine/enamine formation, aldol condensations, reduction..... The world is big; keep exploring. OH Br B Pd(PPh3)4 NaOAc THF-H₂O + HO CH3 CH3
Predict the products/intermediates of the following nucleophilic substitution reactions. ... NaN3 Ph acetone intermediate DCM, rt (2 products) Br PHSH (2 products) OBoc PhMgBr CuBr OMe
A student attempted to prepare 1-chlorobutane by mixing 1-butanol with NaCl in acetone. Was the student succesful? Explain.
Alcohols react with acyl chlorides in the presence of tertiary amines to yield esters.' As described in the cited article, the mechanism of this reaction could involve either a ketene intermediate (R'CHCO) or an acylammonium intermediate (R'CH;CONR;*). NR3 R2OH R HNR3* CI- `OR2 1- methanol (MeOD) as the nucleophile. Different ester products would result upon the operation of mechanism A or B. Draw them in the boxes below. To distinguish between these mechanisms, the cited authors used deuterated Mechanism A Mechanism B MeOD pentane When NET; is used, a mixture of the two products results. Use of pyridine (CSHSN) results in the almost exclusive operation of mechanism B. Propose an explanation for the difference in mechanism between the two amines.
Which of the following reaction scheme leads to the synthesis of 4,4-Dimethylhex-2-yne? ... 1) NANH2, NH3 2) CH3I I. 1) NaNH2, NH3 2) Br II. Br NANH2 NH, (1) Br A) I and II в I only © I only Il and II
Suggest a reasonable series of synthetic transformations to convert 2-methylpropane to 1-bromo-2-methylpropane. Give the appropriate reagent/solvent/catalyst for every step. The conversion should be done in no more than three steps. You can use any substance. (example: 1. CH3MGB., THF; 2. H30+ shows a two-step synthesis. You don't need to worry about superscripts/subscripts. Some common abbreviations used in the class are accepted here. For instance, TsCl=p-toluenesu Ifonyl chloride; NaOMe=sodium methoxide; NaOEt=sodium ethoxide) T T T Arial 3 (12pt) Path: p Words:0
1. a) contd. then write the intermediates for steps i-iii (no need for mechanisms, ATQ) b) What are the intermediate products & the final product of this synthetic sequence? Benzene Br₂ FeCl3 Mg ether 1. C6H5CHO 2. H3O+ H₂Cr₂O4 acetone
It is typically very difficult to do a substitution reaction on an aromatic ring when the leaving group is flanked by two other bulky substituents. Moreover, in Section 22.3, we found that nucleophilic aromatic substitution requires strongly electron-withdrawing groups on the benzene ring. However, Pd-catalyzed coupling allows entry into such products. As examples, write the products of the following reactions and state which coupling reaction is being utilized.
Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.
Synthesize the following compound from cyclohexanone and any other organic compound and provided reagents. 1) (CH3); CuLi (1) Br2, CH300H (1) CH3B1 C. A. В. (2) H20 (2) Li¿CO2, LiBr, DMF (2) H20 heat NaOEt, E1OH D. OH, H20 E. (1) CH3CI, DMF F. CH2(CN)2 (2) H30" Part 1 out of 3 edit structure .. Organic compound
CH3 Ph3P-CHCH3 H3C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. Ph3P-CHCH3 H3C The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an S 2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene :0: CH3 Com The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C-C bond is precisely where the C=O bond was in the reactant and no isomers (other than…
Which reagent/catalyst would be expected to bring about the following conversion? OCH;CH3 CH3CCH,CH3 kCH,CH3 Visited ÓCH,CH3 HNO3 / H2SO4 CH;CH2OH / H3O* O K,Cr2O7/ H2SO4 (1) NABH4 (2) H3o* Ag(NH3),* / OH"