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(a)
Interpretation:
The structure of mesitoic acid is to be predicted. The stable conformation of the mesitoic acid at the bond ring is to be stated.
Concept introduction:
The rotation around single bonds in the stereoisomers of that compound is known as conformational isomers. The system in which two methyl groups are present at
The system in which two substituents are present on the adjacent atoms are known as eclipsed conformation.
(b)
Interpretation:
The reason as to why the acid-catalyzed hydrolysis of the methyl ester of the mesitoic acid does not occur at a measurable rate is to be stated.
Concept introduction:
The reaction in which the hydrolysis of an ester into alcohol and
(c)
Interpretation:
Whether acid-catalyzed esterification in methanol or esterification with diazomethane should be used to make the methyl ester of mesitoic acid is to be stated. The reason for the corresponding answer is to be explained.
Concept introduction:
The reaction in which the hydrolysis of an ester into alcohol and carboxylic acid takes place in the presence of an acid catalyst, is commonly known as acid-catalyzed hydrolysis of an ester.
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Chapter 21 Solutions
EBK ORGANIC CHEMISTRY
- (a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enalarrow_forward(ii) The elimination reaction between 2-bromobutane and NaOCH2CH3 gives two organic products. Draw a mechanism for the reaction which produces the major organic elimination product and provide a rationale as to why that is the major product.arrow_forwardShow 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-methylanilinearrow_forward
- (a) Which is the correct structure of the alkyl halide substrate? (b) Which is the correct structure of the nucleophile?arrow_forward(a) Explain why an alkylamine is more basic than ammonia?(b) How would you convert(i) Aniline to nitrobenzene (ii) Aniline to iodobenzenearrow_forwardWhich is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenolarrow_forward
- Give the reaction mechanism for ETHYNE and bromine solution. Draw and explain the steps of the reaction mechanism.arrow_forwardPhenylacetone can form two different enols.(a) Show the structures of these enolsarrow_forward(a) Which of the following will NOT produce a carboxylic acid or carboxylate ion? 1-butanol + H2CrO4 2-butene + O3/H2O2 butanal + PCC butanal + H2CrO4 (b) Which of the following will NOT produce a carboxylic acid or carboxylate ion? 1-butanol + H2CrO4 2-butene + O3/H2O2 butanal + PCC butanal + H2CrO4arrow_forward
- (i) Name, draw and describe the organic product of the reaction between 2-methylbut-1-ene and H2O in the presence of H2SO4 and provide a clear rationale as to why this is the major product of the reaction. (ii) The elimination reaction between 2-bromobutane and NaOCH2CH3 gives two organic products. Draw a mechanism for the reaction which produces the major organic elimination product and provide a rationale as to why that is the major product.arrow_forward1) 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 COOHarrow_forward1) How will you describe whether any compound has been oxidized or reduced? Support the answer with suitable examples. 2)Why carboxylic acid with a carbonyl group at 3rd position can be decarboxylated? 3) Explain why electrophilic aromatic substitution in Pyrrole takes place at C-2 positions whereas, in Pyridine it takes place at C-3 position? 4) List the following esters in order of decreasing reactivities towards hydrolysis with reason: Methyl benzoate, p-cyano methyl benzoate and p-hydroxy methyl benzoate 5)LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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