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Questions and Answers
Which of the following molecule does not have alpha-hydrogen?
Which of the following molecule does not have alpha-hydrogen?
Which one of the following molecules does not form enol/enolate ion?
Which one of the following molecules does not form enol/enolate ion?
Which one of the following molecules has the most acetic alpha proton?
Which one of the following molecules has the most acetic alpha proton?
Which will form the most stable enol/enolate ion among the following?
Which will form the most stable enol/enolate ion among the following?
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The aldol addition product of the following reaction is:
The aldol addition product of the following reaction is:
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The aldol dehydration product of the following reaction is:
The aldol dehydration product of the following reaction is:
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Predict the structure of the product from the following intramolecular aldol condensation reaction:
Predict the structure of the product from the following intramolecular aldol condensation reaction:
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Deduce the structure of the diketone, which will produce the following cyclic compound by intramolecular aldol condensation. Use retrosynthetic analysis.
Deduce the structure of the diketone, which will produce the following cyclic compound by intramolecular aldol condensation. Use retrosynthetic analysis.
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Which one of the following pairs of carbonyl compounds would be the best choice for a mixed aldol reaction?
Which one of the following pairs of carbonyl compounds would be the best choice for a mixed aldol reaction?
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Predict the product of the following Claisen condensation reaction:
Predict the product of the following Claisen condensation reaction:
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Which one of the following esters will not undergo Claisen ester condensation?
Which one of the following esters will not undergo Claisen ester condensation?
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Predict the product of Dieckmann cyclization of the following ester:
Predict the product of Dieckmann cyclization of the following ester:
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Predict the major product from alkylation of enolate reaction:
Predict the major product from alkylation of enolate reaction:
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The structure of the product from the multistep reaction is:
The structure of the product from the multistep reaction is:
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How many alpha hydrogens are in 2-pentanone?
How many alpha hydrogens are in 2-pentanone?
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Explain why the equilibrium shown favors the enol tautomer.
Explain why the equilibrium shown favors the enol tautomer.
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Which one of the following compounds does not undergo an aldol addition reaction in the presence of aqueous sodium hydroxide?
Which one of the following compounds does not undergo an aldol addition reaction in the presence of aqueous sodium hydroxide?
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What is the predicted product when cyclohexanone reacts with aqueous sodium hydroxide at 100°C?
What is the predicted product when cyclohexanone reacts with aqueous sodium hydroxide at 100°C?
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What reactant would give the aldol condensation product shown?
What reactant would give the aldol condensation product shown?
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Which of the choices is a major product in a Claisen condensation?
Which of the choices is a major product in a Claisen condensation?
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What is the predicted product of the reaction shown?
What is the predicted product of the reaction shown?
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Name the aldehyde or ketone that is used as a preservative for storing biological specimens.
Name the aldehyde or ketone that is used as a preservative for storing biological specimens.
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What is the IUPAC name for the compound shown?
What is the IUPAC name for the compound shown?
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What is the IUPAC name for the compound shown?
What is the IUPAC name for the compound shown?
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What is the IUPAC name for the compound shown?
What is the IUPAC name for the compound shown?
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What is the structure of 4-methylbenzaldehyde?
What is the structure of 4-methylbenzaldehyde?
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What is the predicted major organic product of the reaction shown below?
What is the predicted major organic product of the reaction shown below?
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What is the predicted product for the reaction shown?
What is the predicted product for the reaction shown?
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What is the predicted product of the reaction shown?
What is the predicted product of the reaction shown?
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Compound A on ozonolysis yields acetophenone and propanal. What is the structure of compound A?
Compound A on ozonolysis yields acetophenone and propanal. What is the structure of compound A?
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What is the predicted product of the reaction shown?
What is the predicted product of the reaction shown?
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Predict the major product for the reaction shown.
Predict the major product for the reaction shown.
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What reagents are necessary to carry out the conversion shown?
What reagents are necessary to carry out the conversion shown?
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What is the predicted product of the reaction shown?
What is the predicted product of the reaction shown?
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Provide the reagents necessary to carry out the conversion shown.
Provide the reagents necessary to carry out the conversion shown.
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Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution.
Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution.
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What is the predicted product of the reaction shown?
What is the predicted product of the reaction shown?
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Study Notes
Aldol and Claisen Reactions
- Aldol addition involves the reaction of aldehydes or ketones in the presence of a base, forming β-hydroxy aldehydes or ketones.
- Aldol dehydration results in the formation of α,β-unsaturated carbonyl compounds.
- Claisen condensation produces β-keto esters or β-hydroxy esters from the reaction of two esters or an ester and a carbonyl compound in the presence of a strong base.
- Intramolecular aldol condensation typically yields cyclic compounds.
Key Molecular Features
- Alpha-hydrogens are crucial for enolate formation; molecules lacking these are unable to undergo certain reactions.
- Stability and acidity of α-hydrogens can vary based on molecular structure.
- Compounds with two or more OR groups on the same carbon are classified as acetals.
- The presence of electron-withdrawing groups increases acid strength and can affect nucleophilic addition reactivity.
Predictive Outcomes
- Major products of reactions can be determined based on the functional groups and reaction conditions.
- The structure of diketones can be deduced through retrosynthetic analysis and reaction predictions.
- Different carbonyl compounds can be paired for optimal mixed aldol reactions, emphasizing reactivity differences.
Spectroscopic Analysis
- NMR spectra can provide insight into molecular structure; singlet peaks indicate symmetry.
- IR spectroscopy identifies functional groups based on characteristic absorption patterns.
Reactivity Trends
- Carboxylic acid derivatives exhibit varying reactivity towards nucleophilic substitution based on their structure.
- Factors affecting nucleophilic addition include sterics and electronic effects from substituents on the carbonyl.
Application and Reaction Conditions
- Specific reagents are required for various conversions and reactions, such as PCC for oxidation or lithium aluminum hydride for reduction.
- The reaction conditions, like temperature and presence of solvents, drastically change the outcome or favor the formation of specific tautomers.
Summary of Key Insights
- Understanding the mechanisms and predictions in organic chemistry is vital for successful synthesis.
- Recognition of molecular structure influences how reactions proceed, the stability of intermediates, and the final products formed.
Studying That Suits You
Use AI to generate personalized quizzes and flashcards to suit your learning preferences.
Description
Test your knowledge with these flashcards for the 3rd exam in Organic Chemistry. This quiz covers key concepts such as alpha-hydrogens, enol/enolate ions, and stability of protons. Perfect for revision and self-assessment before the exam.
