16 Questions
What is a characteristic of ethers that makes them good solvents?
Their ability to form hydrogen bonds.
What is the name of the reaction that involves the formation of an ether from an alkoxide and an alkyl halide?
Williamson ether synthesis.
What is the product of the cleavage of an ether with HBr?
An alkyl halide and an alcohol.
What is the reagent used in the base-promoted cyclization of halohydrins to form an epoxide?
Sodium hydroxide.
What is the type of reaction that occurs when an epoxide reacts with a Grignard reagent?
Ring opening of the epoxide.
What is the term used to describe an alkene system that has alternating double bonds?
Conjugated.
What is the correct order of stability for carbocations?
Benzylic > Allylic > Vinyl
What is the intermediate formed in the reaction of an allylic halide with a strong base?
Allylic anion.
Which of the following is a factor that affects the rate of a Diels-Alder reaction?
Steric hindrance
What is the characteristic of an allylic system that allows it to form a stable intermediate?
Stabilization by resonance.
What is the term for the conformer of a diene that is necessary for a Diels-Alder reaction to occur?
s-Cis conformer
Which of the following species is aromatic?
Cycloheptatrienyl cation
What is the term for the product of a Diels-Alder reaction where the electron-withdrawing group is endo to the diene?
Endo product
Which of the following is NOT a condition for a species to be aromatic?
The presence of a leaving group
What is the term for the intermediate formed in an allylic halide reaction with a nucleophile?
Allylic carbocation
Which of the following is an example of a heterocyclic species?
Pyridine
Study Notes
Chapter 14 - Ethers
- Properties of ethers:
- Boiling point
- Hydrogen bonding
- Solvent abilities
- Complexing ability
- Formula and nomenclature of ethers:
- Writing the formula for an ether given its name
- Writing the name for an ether given its formula
- Includes cyclic ethers
- Williamson ether synthesis:
- Predicting the product of the reaction
- Predicting the reactants needed to produce an ether
- Utilizing alkoxymercuration-demercuration to synthesize an ether
- Ether cleavage:
- Predicting the products of ether cleavage by HBr or HI
- Predicting the ether needed to yield products in a cleavage reaction
- Includes aromatic ethers
- Epoxide synthesis and reactions:
- Methods for synthesizing epoxides (peroxyacids and base-promoted cyclization of halohydrins)
- Mechanism for epoxide synthesis reactions
- Acid and base catalyzed ring opening of epoxides
- Reaction of epoxides with Grignard reagents
- Cleavage of ethers
- Multistep reactions involving ethers:
- Completing multistep reactions involving ethers
Chapter 15 - Conjugated Systems
- Identifying and understanding:
- Cumulated (allene system)
- Conjugated systems
- Isolated systems
- Which alkene or alkene system is more stable
- Allylic cation and systems:
- Identifying allylic carbons
- Writing resonance structures for allylic systems
- Stability of carbocations
- Predicting products involving allylic carbocation intermediates
- Predicting products of allylic halides with nucleophiles
- 1,2 and 1,4 addition products in the reaction of a conjugated system
- Resonance structures:
- Drawing resonance structures for allylic and benzylic cations, anions, and free radicals
- Free radical reactions:
- Predicting the products of free radical reactions of allylic and benzylic systems
- Diels-Alder reactions:
- Predicting which Diels-Alder reaction will occur at a faster rate
- Factors affecting Diels-Alder reaction rate: s-cis vs s-trans conformations, electron withdrawing/donating groups, and steric hindrance
- Predicting the product of a Diels-Alder reaction (stereochemistry, orientation of electron withdrawing/donating groups, and the endo rule)
- Using resonance structure to explain why a specific product is obtained
- Predicting the reactants needed to synthesize a product in a Diels-Alder reaction
Chapter 16 - Aromaticity
- Determining aromaticity:
- Whether a species is aromatic, nonaromatic, or antiaromatic
- Includes ionic species and heterocyclic species
- Understanding reactivity based on aromaticity
- Aromatic compounds:
- Writing the name for an aromatic compound given its formula
- Understanding acidity, basicity, and reactivity based on aromaticity
- Placing electron pairs within the ring or outside the ring based on whether or not they are included in the aromatic system
Test your understanding of ethers, including their properties, formula and nomenclature, and Williamson ether synthesis. Assess your knowledge of boiling points, hydrogen bonding, solvent abilities, and complexing ability.
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