2. A chemist was charged with the task of making amino alcohol 2. This chemist decided to attempt a Grignard reaction between two equivalents of phenylmagnesium bromide and amino ester 1. To this end, two equivalents of the Grignard reagent were added to a flask containing a stirred THF solution of ester 1 at -78 °C. Upon acidic aqueous work-up of the reaction mixture, the desired alcohol 2 was not isolated, even though one equivalent of methanol was produced and all the starting materials were consumed. Instead, two products with the molecular formulae of C6H6 and C7H₁3NO were obtained in a 2:1 ratio, respectively. Identify the structures of these two products and describe, mechanistically, how they were formed. MgBr + MeO (2 equivalents) O Me Me 1 Me Me HO + MeOH NH2 NH₂ 2

2. A chemist was charged with the task of making amino alcohol 2. This chemist decided to attempt a Grignard reaction between two equivalents of phenylmagnesium bromide and amino ester 1. To this end, two equivalents of the Grignard reagent were added to a flask containing a stirred THF solution of ester 1 at -78 °C. Upon acidic aqueous work-up of the reaction mixture, the desired alcohol 2 was not isolated, even though one equivalent of methanol was produced and all the starting materials were consumed. Instead, two products with the molecular formulae of C6H6 and C7H₁3NO were obtained in a 2:1 ratio, respectively. Identify the structures of these two products and describe, mechanistically, how they were formed. MgBr + MeO (2 equivalents) O Me Me 1 Me Me HO + MeOH NH2 NH₂ 2

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Similar questions

Make a systematic process for the synthesis of the benzene derivative from benzene. Present all the needed reagent and reaction conditions and products. (Note the electron-donating or electron- withdrawing) NH2
5 In the Fischer esterification reaction, a carboxylic acid reacts with an excess of alcohol in acidic conditions to form an ester. During the reaction the sp2 hybridized carbonyl carbon of the acid forms an sp3 hybridized intermediate before returning to sp² hybridization in the product. Draw the structure of the neutral sp³ hybridized intermediate and the ester product in the reaction between pentanoic acid and n-propanol. pentanoic acid + n-propanol Draw the neutral sp³ intermediate. Select Draw Templates More C H O H* propanol neutral sp³ intermediate Erase Draw the ester product. ester product Select Draw Templates More C H O Erase
20. Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxychloride (POCI3) in pyridine. The alcohol reacts with phosphorus oxychloride much like it reacts with tosyl chloride, displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a reasonable mechanism for the dehydration of 2- methylcyclohexanol by POCl 3 in pyridine.
H₂C OEt H₂C OEt 1. NaOEt, EtOH 2. H₂O* H₂C EtOH OEt Esters, like aldehydes and ketones, are weakly acidic. Treatment of an ester with 1 equivalent of a strong base, such as sodium ethoxide, causes a reversible carbonyl condensation to occur that forms a ẞ-ketoester. This reaction is known as the Claisen condensation. The tetrahedral intermediate thus formed expels an alkoxide leaving group to give an acyl substitution product, a ẞ-ketoester. The steps leading up to this point are all reversible. The best yields for the Claisen condensation are obtained when the starting ester has more than one acidic a-hydrogen. In these cases, a second deprotonation of the a-carbon drives the reaction equilibrium toward the product, thus requiring a full equivalent of base instead of a catalytic amount. Subsequent protonation with dilute aqueous acid resultsn a high yield of the final product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing…
Compound EE, C4H8O shows a positive result (formation of yellow precipitate) when reacted with lodoform reagent. Reduction of compound EE with sodium boron hydride, NABH4 followed by acidified water, H3O* produces an alcohol FF. Compound FF is treated with phosporus pentachloride, PCI5 to form compound GG. Prolong heating of compound EE with concentrated solution of acidified potassium permanganate, KMNO4 will form compound HH and II. Sebatian EE, C4H8O menunjukkan keputusan positif (pembentukkan mendakan kuning) apabila bertindak balas dengan reagen lodoform. Penurunan sebatian EE dengan natrium boron hidrida, NaBH4 diikuti dengan air berasid, H30* menghasilkan satu alkohol FF. Sebatian FF telah dirawat dengan fosforus pentaklorida, PCI5 untuk membentuk sebatian GG. Pemanasan yang berterusan bagi sebatian EE dengan larutan pekat kalium permanganat, KMNO4 berasid akan membentuk sebatian HH dan II. Draw the structural formula of EE, FF, GG, HH and II. Lukiskan formula struktur bagi EE,…
Propose a synthesis for 3,5-dibromo-2-hydroxybenzoic acid (3,5-dibromosalicylic acid) from phenol.
Bb.55.
2) Cinnamaldehyde is one of the primary constituents of cinnamon oil and contributes significantly to the odor of cinnamon. Starting with benzaldehyde and using any other necessary reagents, show how you might prepare cinnamaldehyde. Give your answer as a scheme. Ay H cinnamaldehyde
7. Compound AA, C4H®O, gives a positive result (formation of a silver mirror) when reacted with Tollen's reagent. Reduction of compound AA with lithium aluminium hydride, LİAIH4 followed by acidified water, H3O* produces an alcohol, BB. Oxidation of BB with hot acidified potassium dichromate, K2Cr207 gives butanoic acid, C3H7COOH. Esterification between butanoic acid and methanol, CH3OH produces compound CC. Dehydration of compound BB using concentrated sulphuric acid, H2SO4 at a temperature of 180°C produces compound DD.
Because phenol (C6H5OH) is less acidic than a carboxylic acid, it can be deprotonated by NaOH but not by the weaker base NaHCO3. Using this information, write out an extraction sequence that can be used to separate C6H5OH, benzoic acid, and cyclohexanol. Show what compound is present in each layer at each stage of the process, and if it is present in its neutral or ionic form.
6. Identify compound X in the scheme below. Ph LiAlH4 Et₂O then aqueous workup Dess-Martin or Ley or Swern or PDC compound X
Hh.10.