Organic Chemistry Chapter 14: Ethers

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Questions and Answers

What is a characteristic of ethers that makes them good solvents?

Their high boiling points.

Their ability to form hydrogen bonds. (correct)

Their low reactivity.

Their high viscosity.

What is the name of the reaction that involves the formation of an ether from an alkoxide and an alkyl halide?

E1 elimination reaction.

Friedel-Crafts alkylation.

Alkoxymercuration-demercuration.

Williamson ether synthesis. (correct)

What is the product of the cleavage of an ether with HBr?

A ketone and a halogen.

An alkyl halide and an alcohol. (correct)

An alkoxide and a halogen.

An epoxide and a halogen.

What is the reagent used in the base-promoted cyclization of halohydrins to form an epoxide?

Sodium hydroxide. Signup and view all the answers

What is the type of reaction that occurs when an epoxide reacts with a Grignard reagent?

Ring opening of the epoxide. Signup and view all the answers

What is the term used to describe an alkene system that has alternating double bonds?

Conjugated. Signup and view all the answers

What is the correct order of stability for carbocations?

Benzylic > Allylic > Vinyl Signup and view all the answers

What is the intermediate formed in the reaction of an allylic halide with a strong base?

Allylic anion. Signup and view all the answers

Which of the following is a factor that affects the rate of a Diels-Alder reaction?

Steric hindrance Signup and view all the answers

What is the characteristic of an allylic system that allows it to form a stable intermediate?

Stabilization by resonance. Signup and view all the answers

What is the term for the conformer of a diene that is necessary for a Diels-Alder reaction to occur?

s-Cis conformer Signup and view all the answers

Which of the following species is aromatic?

Cycloheptatrienyl cation Signup and view all the answers

What is the term for the product of a Diels-Alder reaction where the electron-withdrawing group is endo to the diene?

Endo product Signup and view all the answers

Which of the following is NOT a condition for a species to be aromatic?

The presence of a leaving group Signup and view all the answers

What is the term for the intermediate formed in an allylic halide reaction with a nucleophile?

Allylic carbocation Signup and view all the answers

Which of the following is an example of a heterocyclic species?

Pyridine Signup and view all the answers

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

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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.