Consider the reaction below to answer the following questions:847Acetoacetic ester can be prepared by the Claisen self-condensation reaction of ethyl acetate.H₁C0H0IL유||OCH2CH31. NaOEt, EtOH C2. H₂OH3CCH₂Cold not tobizmo. SOCH2CH3A. Write the complete stepwise mechanism for this reaction. Show all electron flow with arrows anddraw all intermediate structures.B. Ethyl acetate can be prepared from ethanol as the only organic starting material. Show all reagentsand structures for all intermediates in this preparation.C. Give the structures of the ester precursors for the following Claisen condensation product andformulate the reaction.ouOEL

Step 1: (A)Step 2: (B)Step 3: (C)

Answered: Consider the reaction below to answer…

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

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.55P

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Complete the reactions given below
Question 9 The reagent which converts a carbonyl group of a ketone into a enamine group is O CH3CH2CH2NHCH3; H CH3CH2CH2NH2; H* O CH3CH2CH2NHCH3; H3O* O CH3CH2CH2NH2; OH OLIAIH[OC(CH3)3]3
For each of the given reactions, pick the correct description and the correct reagent.
Be sure to answer all parts. An allylic alcohol contains an OH group on a carbon atom adjacent to a C-C double bond. Treatment of allylic alcohol A with HCl forms a mixture of two allylic chlorides, B and C. Select a stepwise mechanism that illustrates how both products are formed. HCT + H;O B. Part 1: Select the correct first step. :CI: :C: OH ä: HO. OH :CI: HO. Part 2 out of 4 Select all the appropriate resonance structures that result from the first step that is reproduced below. → resenance structures + H;O Next part
1. NaOEt CO₂Et 2. H3O+ 3. heat Br H3C CO₂H CO2 H3C CO₂Et The malonic ester synthesis is a carbonyl alkylation reaction. It is used to prepare carboxylic acids from primary alkyl halides, lengthening the carbon chain by two atoms. Thus, the product can be visualized as being a "substituted acetic acid." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 22 CX EtO₂C EtO₂C HOCH2CH3 HOCH2CH3 EtO₂C EtO₂C
Claisen condensation between diethyl phthalate and ethyl acetate followed by saponifi- cation, acidification, and decarboxylation forms a diketone, C,H,O,. COOEt 1. EtO Na+ HCI, H,O B NaOH, H,O + CH3COOEt C,H,O2 2. НС, Н,О heat heat COOEt Diethyl phthalate Ethyl acetate Propose structural formulas for compounds A and B and the diketone.
1. NaOEt CO₂Et 2. H3O+ 3. heat Br H3C H₁C CO₂Et CO₂H CO2 + EtOH The malonic ester synthesis is a carbonyl alkylation reaction. It is used to prepare carboxylic acids from primary alkyl halides, lengthening the carbon chain by two atoms. Thus, the product can be visualized as being a "substituted acetic acid." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions EtO₂C X ¯:0: :0: Br: EtO₂C. Br CH3 H3C CH3 CH3 56
HO. Chrysanthemic acid TsO. X Chrysanthemyl tosylate HO. Xnd- Chrysanthemyl alcohol H₂O DMSO Xx OH Artemesia alcohol Yomogi alcohol H₂O: OH Chrysanthemic acid occurs as a mixture of esters in flowers of the chrysanthemum (pyrethrum) family. Reduction of chrysanthemic acid to its alcohol, followed by conversion of the alcohol to its tosylate, gives chrysanthemyl tosylate. Solvolysis of the tosylate gives a mixture of artemesia and yomogi alcohols. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. + :OH₂
Consider the formation of n-butyl bromide from the reaction of n-butyl alcohol with NaBr and H₂SO4. H₂O OH + NaBr + H,SO, Select the leaving group in this reaction. Он о OH Br O H₂O + NaHSO, + H₂O
Rank the following esters from most reactive to least reactive in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate): Rank the same esters from most reactive to least reactive in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).
Reaction with which of the following compounds in an acetylide reaction would lengthen the carbon chain by one carbon and add a primary alcohol? O ethanal O formaldehyde О ерохide O acetone O carbonic acid QUESTION 4 The reagent/reaction of choice for this reduction is || HC-CH=CH-CH2CH2CH2 CO2H CH2OH-CH=CH-CH2CH2CH2 CO2H O lithium aluminum hydride O potassium permanganate O sodium borohydride O Grignard reaction O SN2 reaction
10. Write chemical equations for the reaction of ethyl propanoate with each reagent below. a) LIAIH4/ H3O* b) NH3 d) NaOH c) C2H5NH2

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