4) An undergraduate researcher, James, was given the task of removing a t-butyl ether from thetyrosine derivative A to release the free phenol. James looked up a standard t-butyl ether removalprocedure and ran the reaction. Instead of getting the desired product, B, he got a high yield of C.Show a reaction mechanism that explains why James did not get the desired product. Make sureyour mechanism explains why James only got the ortho product.AHO.NHACNHACOBnOBnHONHACF3C OHOBnDCM, r.t.B 0% yieldC 99% yield

The proposed reaction mechanism explains why James obtained the ortho product (C) instead of the…

Answered: 4) An undergraduate researcher, James,…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 39MP

See similar textbooks

Similar questions

b) Show a complete reaction mechanism for the synthesis of compound K via malonic ester synthesis. Show all the reagents and draw the intermediate structures. COOH Compound K
Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound. (a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin that results. (b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms.
How might you convert geraniol into either ethyl geranylacetate or geranylacetone?
The carboxylic acid G can be converted into the lactone H. Give a reagent for the above reaction.
Draw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with following reagent. With some reagents, no reaction occurs. [1] SOCl2; [2] CH3CH2CH2NH2 (excess)
Based on the image attached, it shows methyl salicylate reacts with Ethanamine, and Ether act as a solvent to form N-ethylbenzamide as a product. Explains the mechanism reaction of conversion ester to an amide.
under basic condition
Vanillin has an acidic OH and an electrophilic aldehyde group that could conceivably react with sodiumhydroxide. However, in the aldol reaction, you added the NaOH directly to the solution of vanillin andacetone, rather than pre-treating acetone with base. Why could you do this successfully? a) NaOH is a weak base and a weak nucleophile.b) The reaction of NaOH with phenol OH groups and aromatic aldehydes is reversible, and thereaction is driven to the most stable product.c) The aldehyde in vanillin is unreactive towards nucleophiles.d) The NaOH is not soluble in the reaction
A tosylate is synthesized by reaction of p-toluenesulfonic acid with a(n) __________. amine ester ether carboxylic acid alcohol Cyclohexanol plus chromic acid reagent will yield __________. cyclohexan-1,1-diol cyclohexanone cyclohexan-1,2-diol hexan-1,6-diacid
The conjugate base of diethyl malonate can serve as a nucleophile to attack a wide range of electrophiles. Identify the product that is formed when the conjugate base of diethyl malonate reacts with the following electrophile followed by acid workup when relevant: CN Modify the provided structures of diethyl malonate and the given electrophile to draw the product formed. Note: the eraser tool can be used to erase bonds, and atoms can be moved by selecting them with the selector tool and then dragging the selected atom(s) to a new position. If you make a mistake, you can use Ctrl-Z or the Undo tool. EtO H3C CN Edit Drawing OEt
Draw mechanisms for the acetylation of aniline, the bromination of acetanilide and the hydrolysis of 4-bromoacetanilide (REMEMBER: NBS generates bromine in solution) Reagents used: aniline, acetic acid, acetic anhydride to make acetanilide. Then acetanilide dissolved in acetic acid, NBS, aqHBr to make 4-bromoaxetanilinde. Then 4-bromoacetanilinde, EtOh, HCl and NaOH (to neutralise) to make 4-bromoaniline Please include drawings of the mechanisms as well as a written explanation as it helps me process exactly whats going on...
22) NM₂2 in N,N-dimethylaniline ( is ortho-para director but it gives meta product in reaction with one of the following reagents. Identify the reagent. a) Br₂ b) c) HNO3 H₂SO4 O ات

SEE MORE QUESTIONS

Recommended textbooks for you

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry: A Guided Inquiry

Chemistry

ISBN:

9780618974122

Author:

Andrei Straumanis

Publisher:

Cengage Learning

EBK A SMALL SCALE APPROACH TO ORGANIC L

Chemistry

ISBN:

9781305446021

Author:

Lampman

Publisher:

CENGAGE LEARNING - CONSIGNMENT

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry: A Guided Inquiry

Chemistry

ISBN:

9780618974122

Author:

Andrei Straumanis

Publisher:

Cengage Learning

EBK A SMALL SCALE APPROACH TO ORGANIC L

Chemistry

ISBN:

9781305446021

Author:

Lampman

Publisher:

CENGAGE LEARNING - CONSIGNMENT

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

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

Publisher:

Cengage Learning

SEE MORE TEXTBOOKS