1. Op 2,5-dimethylcyclopentanone can be prepared by a multistep procedure from diethyl adipate and methyl iodide as key organic sources. Predict reagents, show key steps, key intermediates and/or mechanisms for the sequence. • As a hint, dietbylcarbonate should be a byproduct in the last transformation.

1. Op 2,5-dimethylcyclopentanone can be prepared by a multistep procedure from diethyl adipate and methyl iodide as key organic sources. Predict reagents, show key steps, key intermediates and/or mechanisms for the sequence. • As a hint, dietbylcarbonate should be a byproduct in the last transformation.

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 16.47P: The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii...

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2. (a) Ozonolysis of compound A, C,H12 gave two products B and C. Further analysis of these two compounds of B and C, showed positive results with 2,4-dinitrophenylhydrazine. Compound B reacts with Tollens' reagent while compound C does not indicate any positive result to the same reagent. However, both B and C gave same positive results with iodoform test. (i) By writing all the chemical equations involved, identify A, B and C.
Syntheses of each of the following compounds have been reported in the chemical literature. Using the indicated starting material and any necessary organic or inorganic reagents, describe short sequences of reactions that would be appropriate for each transformation. (a) 1,1,5-Trimethylcyclononane from 5,5-dimethylcyclononanone
The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.
(a)Which compound/s will produce an orange precipitate upon reaction with 2,4-DNPH? (b)Which compound/s will test positive towards Baeyer’s test? (c)Which compound/s will produce a brick-red precipitate upon reaction with Fehling’s reagent (CuSO4, tartrate, NaOH)? (d)Which compound/s will test positive towards the Iodoform test?
(c) Consider the antiallergy medication loratadine (Claritin) shown below: Loratadine (Claritin) The reaction to form the portion of the molecule in the red circle is used in the synthesis of loratadine and many other pharmaceutical agents. (i) Propose a suitable starting material and reagents to form the portion of the molecule in the red circle. (ii) Clearly outline the mechanism by which the reaction takes place. In your answer, show how the intermediate ion is stabilized.
(19, 8, 3) Specify a synthetic scheme that would produce the compound shown above in the fewest steps possible. Use one of the starting materials shown together with any of the available reagents. Give the number of the starting material followed by the letters of the reagents in the order of their use, for example: 3be.
(a) 1-methylcyclopentene B can be prepared by an intramolecular Wittig reaction from A. Propose a plausible arrow-pushing mechansim for this the transformation from A to B. (b) Propose a synthesis to convert 1-methylcyclopentene B to the cyclic ester C. Show all intermediates, and reagents necessary for each step.
Provide a retrosynthetic analysis and synthesis for each of the following compounds. Permitted starting materials are phenylmagnesium bromide, oxirane, formaldehyde, and alcohols or esters of four carbon atoms or fewer. You may use any inorganic reagents and oxidizing conditions such as Swern oxidation or pyridinium chlorochromate (PCC). (a) OH OH -of-oto-or (b) H (c) (d) OH
Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.(a) p-aminobenzoic acid (b) 2-methyl-1-phenylbutan-2-ol (c) 5-chloro-2-methylaniline
Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no morethan four carbon atoms as your organic starting materials. Assume that para is the major product (and separable fromortho) in ortho, para mixtures.(a) pentan-1-amine (b) N-methylbutan-1-amine(c) N-ethyl-N-propylbutan-2-amine (d) N-benzylpropan-1-amine(e)N N OH(e) (f) 3-propylaniline(g) 4-isobutylaniline
Each of the following is a set of directions for carrying out a reaction or sequence of reactions. Rewrite each set ofdirections in the form of a synthesis.(a) To 2-ethylcyclohexanone, add lithium diisopropylamide, and when that reaction is complete, add bromoethane toyield 2,6-diethylcyclohexanone.(b) Add molecular bromine to 2,2-dimethylcyclohexanone in the presence of acetic acid to yield 6-bromo-2,2-dimethylcyclohexanone. To the resulting mixture, add sodium cyanide to yield 6-cyano-2,2-dimethyl-cyclohexanone.(c) Treat pent-4-ynoic acid with diazomethane to produce methyl pent-4-ynoate. Next, add sodium hydride, followed by(bromomethyl)benzene, to yield methyl 6-phenylhex-4-ynoate.
Suggest readily available starting materials and reaction conditions suitable for obtaining each of the following compounds by a procedure involving alkylation of nucleophilic carbon. (a) PHCH2CH2CHPH (b) (CH3)½C=CHCH2CH2CCH2CO;CH3 ČN (c) (d) CH2=CHCH=CHCH2CH2CO,H CH3 CH2CO2H CH3 CH3CO CH;CH2CH2 (f) (e) 2,3-diphenylpropanoic acid (g) CH3Oʻ CH3CH2 CH2CH=CH2