Indicate the products obtained in the reaction of 5-nitro-2-heptanone with 1 mol of phenyl magnesium bromide followed by acid hydrolysis. CH3 MgBr CH3 5-nitro-2-heptanone Phenyl magnesium bromide
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- Each of the following reactions has been carried out under conditions such that disubstitution or trisubstitution occurred. Identify the principal organic product in each case. (a) Nitration of p-chlorobenzoic acid (dinitration) (b) Bromination of aniline (tribromination) (c) Bromination of o-aminoacetophenone (dibromination) (d) Bromination of p-nitrophenol (dibromination) (e) Reaction of biphenyl with tert-butyl chloride and iron(III) chloride (dialkylation) (f) Sulfonation of phenol (disulfonation)Indicate how to obtain 4-phenyl-2-butanone starting from ethyl 3-oxobutanoate.Predict the products of the reactions of the following compounds with: (1) chromic acid or excess sodium hypochlorite with acetic acid. (2) PCC or NaOCl (1 equivalent) with TEMPO. (a) cyclohexanol (b) 1-methylcyclohexanol(c) cyclopentylmethanol (d) cyclohexanone
- -Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the -hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the -hydroxyketone or aldehyde. Write a mechanism for the oxidation of this -hydroxyaldehyde by HIO4.Treating a Grignard reagent with carbon dioxide followed by aqueous HCl gives a carboxylic acid. Propose a structural formula for the bracketed intermediate and a mechanism for its formation.The compound 3,5,5-trimethyl-2-cyclohexenone can be synthesized using acetone and ethyl acetoacetate as sources of carbon atoms. New carbon-carbon bonds in this synthesis are formed by a combination of aldol reactions and Michael reactions. Show reagents and conditions by which this synthesis might be accomplished.
- What product would you expect from reaction of one equivalent of methanol with a cyclic anhydride, such as phthalic anhydride (1,2-benzenedicarboxylic anhydride)? What is the fate of the second half of the anhydride?Following is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A. (a) Addition of one mole of HCl to isoprene gives 4-chloro-2-methyl-2-butene as the major product. Propose a mechanism for this addition and account for its regioselectivity. (b) Propose a synthesis of the vitamin A precursor from this allylic chloride and ethyl acetoacetate.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.
- Propose a reaction for the formation of the following products involving esterformation.When benzaldehyde is added to the reagent prepared by reacting ethyl-2-bromoacetate with metallic zinc in benzene, which of the following molecules is obtained when the product is finally acidified.A. 3-phenyl-3-hydroxy-3-propanoate B. ethyl-3-phenylpropanoate C. ethyl-3-hydroxypropanoate D. ethyl-3-phenylpropanoate E ethyl-3-hydroxy-3-phenylpropanoateGive the shortest route to produce the desired products 1. cyclobutanoic acid to ethyl-cyclobutyl ketone 2. 2-butanone to pentatonic acid 3. propane to butanamine