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.

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.

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 28VC

See similar textbooks

Similar questions

Suppose you want to determine the inductive effects of a series of functional groups (e.g., Cl, Br, CN, COOH, and C6H5). Is it best to use a series of ortho-, meta-, or parasubstituted phenols? Explain.
Write a reaction that could be carried out to synthesize 1-(4-methylphenyl)ethanol (reactants will be a combination of Grignard reagent and carbonyl compound).
4) Write the reaction between cyclohexanecarboxylic acid and thionyl chloride showing all three products (two gaseous and one liquid). Take the liquid product and treat it with 2 moles of dimethylamine in benzene as the solvent. You get two products. What are they? Draw their formulae and write their names.
Suggest possible synthetic route for following transformations. Show the reagents, intermediates and products.
Provide the reagents necessary to complete the following reactions.
The following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxide
4. Synthesize the following compound. You may use benzene, acetylene, ethanol and any inorganic reagents. O₂N
Which of the following reactions will synthesize phenol from benzene? 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) warm H2SO4 and H2O 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) CuCN; 5) dilute acid and heat 1) Acetyl chloride & AlCl3; 2) bleach 1) Ph-N2+ + KI; 2) BrMgCH=CH2 in ether, followed by H3O+; 3) warm, conc'd KMnO4 1) Cl-CH(CH3)-CH2CH2CH3 + FeBr3; 2) hot, conc'd KMnO4
Draw each reaction and their steps with preparation. 1) C6H5CH2COC6H5 from benzaldehyde as the only source of carbon. 2) CH3CH2COOCH2CH=CH2 from allyl alcohol as the only carbon source. 3) 1-Phenyl-1-butanone (butyrophenone) from butyraldehyde and benzene.
Synthesize 2-pentanone from 1-butyne. Indicate all the reagents needed.
(b) Answer the following questions based on the compounds below. Jawab soalan berikut berdasarkan kepada sebatian di bawah. CI CI A в (i) Which compound has the higher boiling point? Explain. Sebatian manakah mempunyai takat didih yang lebih tinggi? Terangkan. (ii) Draw the SN2 mechanism for the reaction of compound A with sodium hydroxide, NaOH. Lukis mekanisma Sn2 bagi tindak balas antara sebatian A dengan natrium hidroksida, NaOH.
1) Carry out TWO of the following three synthesis. (You can do the third one for . Provide all the reagents and show all structures of the products formed in each step, not just a list of reagents. a) Benzene b) Benzene c) Toluene p-aminobenzoic acid OHC COOH