Organic Chemistry 3rd Exam Flashcards

Choose a study mode

Play Quiz
Study Flashcards
Spaced Repetition
Chat to Lesson

Podcast

Play an AI-generated podcast conversation about this lesson
Download our mobile app to listen on the go
Get App

Questions and Answers

Which of the following molecule does not have alpha-hydrogen?

  • Choice B
  • Choice C
  • Choice D
  • Choice A (correct)

Which one of the following molecules does not form enol/enolate ion?

  • Choice B
  • Choice A (correct)
  • Choice C
  • Choice D

Which one of the following molecules has the most acetic alpha proton?

  • Choice A
  • Choice C (correct)
  • Choice B
  • Choice D

Which will form the most stable enol/enolate ion among the following?

<p>Choice D (B)</p> Signup and view all the answers

The aldol addition product of the following reaction is:

<p>Choice D (A)</p> Signup and view all the answers

The aldol dehydration product of the following reaction is:

<p>Choice D (C)</p> Signup and view all the answers

Predict the structure of the product from the following intramolecular aldol condensation reaction:

<p>Choice C (A)</p> Signup and view all the answers

Deduce the structure of the diketone, which will produce the following cyclic compound by intramolecular aldol condensation. Use retrosynthetic analysis.

<p>Choice A (D)</p> Signup and view all the answers

Which one of the following pairs of carbonyl compounds would be the best choice for a mixed aldol reaction?

<p>Choice B (A)</p> Signup and view all the answers

Predict the product of the following Claisen condensation reaction:

<p>Choice C (D)</p> Signup and view all the answers

Which one of the following esters will not undergo Claisen ester condensation?

<p>Choice B (C)</p> Signup and view all the answers

Predict the product of Dieckmann cyclization of the following ester:

<p>Choice A (C)</p> Signup and view all the answers

Predict the major product from alkylation of enolate reaction:

<p>Choice B (A)</p> Signup and view all the answers

The structure of the product from the multistep reaction is:

<p>Choice B (D)</p> Signup and view all the answers

How many alpha hydrogens are in 2-pentanone?

<p>5</p> Signup and view all the answers

Explain why the equilibrium shown favors the enol tautomer.

<p>Because it allows the pi bond to be a part of a much more stable aromatic system.</p> Signup and view all the answers

Which one of the following compounds does not undergo an aldol addition reaction in the presence of aqueous sodium hydroxide?

<p>2,2-dimethylbutanal (D)</p> Signup and view all the answers

What is the predicted product when cyclohexanone reacts with aqueous sodium hydroxide at 100°C?

<p>Choice D (B)</p> Signup and view all the answers

What reactant would give the aldol condensation product shown?

<p>Choice A (A)</p> Signup and view all the answers

Which of the choices is a major product in a Claisen condensation?

<p>β-keto ester (D)</p> Signup and view all the answers

What is the predicted product of the reaction shown?

<p>Choice A (B)</p> Signup and view all the answers

Name the aldehyde or ketone that is used as a preservative for storing biological specimens.

<p>Formaldehyde (E)</p> Signup and view all the answers

What is the IUPAC name for the compound shown?

<p>7-methyl-4-octanone (E)</p> Signup and view all the answers

What is the IUPAC name for the compound shown?

<p>5,5-dimethyl-2-heptanone (C)</p> Signup and view all the answers

What is the IUPAC name for the compound shown?

<p>2,5-dimethylhexanal (E)</p> Signup and view all the answers

What is the structure of 4-methylbenzaldehyde?

<p>Choice C (C)</p> Signup and view all the answers

What is the predicted major organic product of the reaction shown below?

<p>Hexanal (B)</p> Signup and view all the answers

What is the predicted product for the reaction shown?

<p>Choice B (A)</p> Signup and view all the answers

What is the predicted product of the reaction shown?

<p>Choice B (D)</p> Signup and view all the answers

Compound A on ozonolysis yields acetophenone and propanal. What is the structure of compound A?

<p>2-phenyl-2-pentene (C)</p> Signup and view all the answers

What is the predicted product of the reaction shown?

<p>Choice D (C)</p> Signup and view all the answers

Predict the major product for the reaction shown.

<p>Choice B (B)</p> Signup and view all the answers

What reagents are necessary to carry out the conversion shown?

<p>Excess CH3MgBr, H2O (D)</p> Signup and view all the answers

What is the predicted product of the reaction shown?

<p>Choice D (D)</p> Signup and view all the answers

Provide the reagents necessary to carry out the conversion shown.

<p>A and C (E)</p> Signup and view all the answers

Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution.

<p>IV &gt; I &gt; III &gt; II (D)</p> Signup and view all the answers

What is the predicted product of the reaction shown?

<p>Choice A (B)</p> Signup and view all the answers

Flashcards

Aldol Addition

Reaction of aldehydes/ketones with a base, forming β-hydroxy aldehydes/ketones.

Aldol Dehydration

Forms α,β-unsaturated carbonyl compounds from Aldol addition, through water removal.

Claisen Condensation

Forms β-keto esters from two esters in the presence of a strong base.

Intramolecular Aldol Condensation

Aldol reaction within the same molecule, creating rings.

Signup and view all the flashcards

Alpha-Hydrogens

Hydrogens on the carbon next to a carbonyl group.

Signup and view all the flashcards

Alpha-Hydrogens & Enolate Formation

Molecules lacking alpha-hydrogens cannot form enolates.

Signup and view all the flashcards

Acetals

Two or more -OR groups bonded to the same carbon atom.

Signup and view all the flashcards

Electron-Withdrawing Groups & Acidity

Increase acid strength by stabilizing conjugate base.

Signup and view all the flashcards

Retrosynthetic Analysis

Determining starting materials from the products.

Signup and view all the flashcards

Mixed Aldol Reactions

Pairing carbonyls with differing reactivity for controlled reactions.

Signup and view all the flashcards

Singlet Peak in NMR

Indicates symmetry within the molecule.

Signup and view all the flashcards

IR Spectroscopy

Identifies functional groups via absorption patterns.

Signup and view all the flashcards

Reactivity Trends

Differences in the rate a molecule reacts based on its structure.

Signup and view all the flashcards

Carboxylic Acid Derivative Reactivity

React differently due to structure.

Signup and view all the flashcards

Steric Effects

Bulkier groups hinder reactions.

Signup and view all the flashcards

Electronic Effects on Nucleophilic Addition

Substituents that donate or withdraw electron density affect rate.

Signup and view all the flashcards

PCC (Pyridinium Chlorochromate)

Used to oxidize primary alcohols to aldehydes.

Signup and view all the flashcards

Lithium Aluminum Hydride (LAH)

A strong reducing agent that reduces carbonyls to alcohols.

Signup and view all the flashcards

Reaction Temperature

Can alter reaction rate, equilibrium, or favor specific products/tautomers.

Signup and view all the flashcards

Tautomers

Shift between constitutional isomers, usually differing in a proton and a double bond location.

Signup and view all the flashcards

Aldol Reaction

A reaction of aldehydes or ketones in the presence of a base, forming β-hydroxy carbonyl compounds

Signup and view all the flashcards

Aldol Addition Mechanism

The enolate reacts with a carbonyl compound to form a new carbon-carbon bond.

Signup and view all the flashcards

Dehydration in Aldol Reactions

The removal of water from an aldol product to form an α,β-unsaturated carbonyl compound.

Signup and view all the flashcards

Claisen Reaction

Reaction between two esters to form a β-keto ester.

Signup and view all the flashcards

Base's Role in Claisen

Deprotonation of an α-hydrogen to form an enolate.

Signup and view all the flashcards

Product of Intramolecular Aldol

A cyclic compound is formed.

Signup and view all the flashcards

Solvent's Role

Affects the outcome or reaction rate.

Signup and view all the flashcards

Carboxylic Acid Derivative Substitution

Differing nucleophilic substitution reactivity based on LG

Signup and view all the flashcards

LAH reducing carbonyls

Strong reduction to alcohols.

Signup and view all the flashcards

Enol Tautomer

Less stable than keto.

Signup and view all the flashcards

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.
  • 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.

Quiz Team

More Like This

Use Quizgecko on...
Browser
Open
Browser
Browser