Concept explainers
(a)
Interpretation:
To identify which of the given reaction is not feasible.
Concept introduction:
The carboxylic acid and its derivatives undergo nucleophilic acyl substitution reaction. The incoming group is called as a nucleophile and the substituent that departs from a molecule is known as leaving the group. If the attacking group is a good base or poor leaving group as compared to the substituent that is already present in the tetrahedral intermediate than attacking group will replace the existing substituent or good leaving group and reaction will be feasible.
(b)
Interpretation:
To identify the reactions which are not feasible in the above part of the question can be made feasible by adding an acid catalyst.
Concept introduction:
The aminolysis reaction and the hydrolysis of ester can be made feasible by the addition of acid catalyst in the reaction mixture.
The acid catalyst first protonates the carbonyl oxygen thus increses the electrophillitcity of the carbonyl carbon and also protonates the nitogen atom making it good leaving group. Thus, the
Want to see the full answer?
Check out a sample textbook solutionChapter 16 Solutions
Organic Chemistry (Package) (Looseleaf)
- Using resonance structures of the intermediates, explain why bromination of biphenyl occurs at ortho and para positions rather than at meta.arrow_forwardFill in the missing reagents a-e in the following scheme:arrow_forwardDraw structures for the carbonyl electrophile and enolate nucleophile that give the enone presentedarrow_forward
- Draw the major organic product of the SN1SN1 reaction:arrow_forwardExplain why compound A does not undergo an E2 elimination with strong base.arrow_forwarda. Rank the following esters from most reactive to least reactive in the first slow step of a nucleophilic acyl substitution reaction (formation of thetetrahedral intermediate): b. Rank the same esters from most reactive to least reactive in the second slow step of a nucleophilic acyl substitution reaction (collapse of thetetrahedralintermediate).arrow_forward
- (a) Which halide in the following marine natural product reacts fastest in the SN2 reaction? (b) Which halide in the following marine natural product reacts fastest in the SN1 reaction?arrow_forwardWhat is the best combination of electrophile and nucleophile that would be the most effective in the synthesis of the following ether?arrow_forwardDraw the major organic product of this E1 elimination reaction. Ignore byproducts.arrow_forward
- Explain why a Lewis acid is necessary in this aldol reaction. Include a structure formed by the Lewis Acid and one of the reactants that is key to your discussion. R group is p-methoxyphenyl to make p-methoxybenzaldehyde (reactant). R' is phenyl.arrow_forwardLDA is the base of choice for carbonyl compound to completely convert into enolate. Why?arrow_forwardKindly draw the product that was fromed when phenylacetic acid was treated with the reagent, show the process and give some explanation. Thanks! a. [1] SOCI2; [2] CH3CH2CH2NH2 (excess) b. [1] SOCI2; [2] (CH3)2CHOHarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT