Podcast
Questions and Answers
What do alcohols, epoxides, and ethers have in common?
What do alcohols, epoxides, and ethers have in common?
- They are all non-polar
- They all have polar C-O sigma bonds (correct)
- They are all gases at room temperature
- They contain a carbonyl group
What do alcohols contain?
What do alcohols contain?
A hydroxy group (OH) bonded to a sp3 hybridized carbon.
What do enols contain?
What do enols contain?
An OH group on a sp2 hybridized carbon of a C-C double bond.
What do phenols contain?
What do phenols contain?
What is an ether characterized by?
What is an ether characterized by?
A symmetrical ether has two different alkyl groups.
A symmetrical ether has two different alkyl groups.
Both alcohols and ethers are organic derivatives of H2O.
Both alcohols and ethers are organic derivatives of H2O.
What is an epoxide?
What is an epoxide?
What is the hybridization of oxygen in alcohols, ethers, and epoxides?
What is the hybridization of oxygen in alcohols, ethers, and epoxides?
The bond angle around the O in an alcohol and ether is ____.
The bond angle around the O in an alcohol and ether is ____.
The C-O-C bond angle of an epoxide is ____.
The C-O-C bond angle of an epoxide is ____.
What suffix is used to identify alcohols in the IUPAC system?
What suffix is used to identify alcohols in the IUPAC system?
When an OH group is bonded to a ring, the ring is numbered ending with the OH group.
When an OH group is bonded to a ring, the ring is numbered ending with the OH group.
What are the two steps in naming an alcohol according to IUPAC?
What are the two steps in naming an alcohol according to IUPAC?
How do you assign simple alcohols a 'common name'?
How do you assign simple alcohols a 'common name'?
What are diols or glycols?
What are diols or glycols?
What are triols?
What are triols?
How do you name simple ethers?
How do you name simple ethers?
How do you name a complex ether?
How do you name a complex ether?
What are the three ways to name an epoxide?
What are the three ways to name an epoxide?
How do you name an epoxide as an epoxyalkane?
How do you name an epoxide as an epoxyalkane?
How do you name an epoxide as an oxirane?
How do you name an epoxide as an oxirane?
How do you name an epoxide as an alkene oxide?
How do you name an epoxide as an alkene oxide?
What interactions do alcohols, ethers, and epoxides exhibit?
What interactions do alcohols, ethers, and epoxides exhibit?
Alcohols are much more polar than ethers and epoxides.
Alcohols are much more polar than ethers and epoxides.
Increasing the number of R groups around the carbon bonded to OH does what to the extent of hydrogen bonding?
Increasing the number of R groups around the carbon bonded to OH does what to the extent of hydrogen bonding?
What are two ways to increase the boiling point of alcohols, ethers, and epoxides?
What are two ways to increase the boiling point of alcohols, ethers, and epoxides?
Determine the solubility conditions for alcohols, ethers, and epoxides:
Determine the solubility conditions for alcohols, ethers, and epoxides:
In the host-guest complex known as the crown ether-cation complex, who is the host and who is the guest?
In the host-guest complex known as the crown ether-cation complex, who is the host and who is the guest?
What is molecular recognition?
What is molecular recognition?
Alcohols and ethers are common products of what reaction?
Alcohols and ethers are common products of what reaction?
Alcohols and ethers are synthesized from alkyl halides in what type of reactions?
Alcohols and ethers are synthesized from alkyl halides in what type of reactions?
What is the Williamson Ether Synthesis?
What is the Williamson Ether Synthesis?
Which path is preferred for synthesizing unsymmetrical ethers?
Which path is preferred for synthesizing unsymmetrical ethers?
What type of nucleophile is needed to synthesize an alcohol?
What type of nucleophile is needed to synthesize an alcohol?
What type of salt is needed to make an ether?
What type of salt is needed to make an ether?
A halohydrin can perform what type of reaction to form an epoxide?
A halohydrin can perform what type of reaction to form an epoxide?
Alcohols and alkyl halides both contain good leaving groups.
Alcohols and alkyl halides both contain good leaving groups.
Why does nucleophilic substitution with ROH not work?
Why does nucleophilic substitution with ROH not work?
What must happen for an alcohol to undergo a substitution reaction?
What must happen for an alcohol to undergo a substitution reaction?
When the alcohol is treated with a strong acid, what does the -OH get converted to?
When the alcohol is treated with a strong acid, what does the -OH get converted to?
What is dehydration?
What is dehydration?
As the substitution of an alcohol increases, what happens to the rate of dehydration?
As the substitution of an alcohol increases, what happens to the rate of dehydration?
What product is considered the major product in dehydration reactions?
What product is considered the major product in dehydration reactions?
What elimination mechanism do 2° & 3° alcohols undergo?
What elimination mechanism do 2° & 3° alcohols undergo?
What elimination mechanism do 1° alcohols undergo?
What elimination mechanism do 1° alcohols undergo?
What are the three steps of a 2°/3° alcohol dehydration?
What are the three steps of a 2°/3° alcohol dehydration?
What are the two steps of a 1° alcohol dehydration?
What are the two steps of a 1° alcohol dehydration?
What is Le Châtelier's Principle?
What is Le Châtelier's Principle?
What is carbocation rearrangement?
What is carbocation rearrangement?
What are the four steps of a 1,2 methyl shift in dehydration?
What are the four steps of a 1,2 methyl shift in dehydration?
In dehydration reactions, what happens when POCl3 is used?
In dehydration reactions, what happens when POCl3 is used?
What is the Protonation of OH from 1° form?
What is the Protonation of OH from 1° form?
What is the Protonation of OH from 2° and 3° form?
What is the Protonation of OH from 2° and 3° form?
What affects the reactivity of hydrogen halide?
What affects the reactivity of hydrogen halide?
What Lewis acid catalyst is used when 1° alcohols react with HCl?
What Lewis acid catalyst is used when 1° alcohols react with HCl?
What kind of stereochemistry do 1° alcohols react in SN2 reaction to form?
What kind of stereochemistry do 1° alcohols react in SN2 reaction to form?
What do 3° alcohols yield when reacting in an SN1 Mechanism?
What do 3° alcohols yield when reacting in an SN1 Mechanism?
Carbocation rearrangement is possible in the SN1 reactions of 2° and 3° alcohols.
Carbocation rearrangement is possible in the SN1 reactions of 2° and 3° alcohols.
What does SOCl2 convert 1° and 2° alcohols into?
What does SOCl2 convert 1° and 2° alcohols into?
What does PBr3 convert alcohols into?
What does PBr3 convert alcohols into?
Summarize converting ROH to RX.
Summarize converting ROH to RX.
Alcohols are converted to alkyl tosylates by treatment of...
Alcohols are converted to alkyl tosylates by treatment of...
Since alkyl tosylates have good leaving groups, they undergo...
Since alkyl tosylates have good leaving groups, they undergo...
Summarize the two-step reaction of an alcohol with TsCl and pyridine.
Summarize the two-step reaction of an alcohol with TsCl and pyridine.
Summarize nucleophilic substitution and β elimination of alcohols.
Summarize nucleophilic substitution and β elimination of alcohols.
The leaving groups of ethers can only be converted to good leaving groups by reaction of which strong acids?
The leaving groups of ethers can only be converted to good leaving groups by reaction of which strong acids?
Since both C-O bonds are broken in an ether, what occurs?
Since both C-O bonds are broken in an ether, what occurs?
The 2° or 3° alkyl groups of an ether oxygen are cleaved by what mechanism?
The 2° or 3° alkyl groups of an ether oxygen are cleaved by what mechanism?
Methyl or 1° alkyl groups are cleaved by what mechanism?
Methyl or 1° alkyl groups are cleaved by what mechanism?
In the mechanism of an ether with a strong acid HX, what is the first step?
In the mechanism of an ether with a strong acid HX, what is the first step?
In the mechanism of an ether with a strong acid HX, what is the second step?
In the mechanism of an ether with a strong acid HX, what is the second step?
Thiols and sulfides are sulfur analogues of what?
Thiols and sulfides are sulfur analogues of what?
What happens during nucleophilic attack on an epoxide?
What happens during nucleophilic attack on an epoxide?
What are the two steps to opening an epoxide ring with a strong nucleophile?
What are the two steps to opening an epoxide ring with a strong nucleophile?
What type of mechanism do strong nucleophiles like -OH, -OR, -CN, -SR, and NH3 use when reacting with epoxides?
What type of mechanism do strong nucleophiles like -OH, -OR, -CN, -SR, and NH3 use when reacting with epoxides?
In an unsymmetrical epoxide, where does the nucleophile attack?
In an unsymmetrical epoxide, where does the nucleophile attack?
If the epoxide is symmetrical, nucleophilic attack occurs from where?
If the epoxide is symmetrical, nucleophilic attack occurs from where?
What are the two steps in the opening of an epoxide ring with H-Z?
What are the two steps in the opening of an epoxide ring with H-Z?
Flashcards
Alcohol
Alcohol
Contains a hydroxyl (OH) group bonded to an sp3 hybridized carbon atom.
Enol
Enol
Has an OH group on a sp2 hybridized carbon involved in a C-C double bond.
Phenol
Phenol
Features an OH group substituted directly on a benzene ring.
Ether
Ether
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Symmetrical Ethers
Symmetrical Ethers
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Unsymmetrical Ethers
Unsymmetrical Ethers
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-ol Suffix
-ol Suffix
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Naming Ethers
Naming Ethers
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Alcohols and Ethers
Alcohols and Ethers
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Dipole-Dipole Interactions
Dipole-Dipole Interactions
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Alcohols
Alcohols
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More Polar
More Polar
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Alcohols And Ethers Solubility
Alcohols And Ethers Solubility
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Increase Intermolecular Forces
Increase Intermolecular Forces
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Nucleophiles
Nucleophiles
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Primary Halides
Primary Halides
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Williamson Ether Synthesis
Williamson Ether Synthesis
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Sterically
Sterically
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Dehydration
Dehydration
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Substituted
Substituted
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E1 Mechanism
E1 Mechanism
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E2 Mechanism
E2 Mechanism
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Carbocation Rearrangement
Carbocation Rearrangement
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Leaving
Leaving
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SN2
SN2
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Racemic
Racemic
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C-O
C-O
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Thiols and Sulfides
Thiols and Sulfides
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Less
Less
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Sn2 Pathways
Sn2 Pathways
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Study Notes
Alcohols, Ethers, and Epoxides
- Alcohols, epoxides, and ethers contain polar C-O sigma bonds.
- Alcohols feature a hydroxy group (OH) bonded to an sp3 hybridized carbon.
- Enols possess an OH group on a sp2 hybridized carbon involved in a C-C double bond.
- Phenols have an OH group substituted on a benzene ring.
- Ethers consist of two alkyl groups connected to a single oxygen atom.
- Symmetrical ethers have identical alkyl groups; unsymmetrical ethers have different ones.
Nomenclature
- Alcohols are identified using the suffix -ol in the IUPAC naming system.
- To name alcohols, first identify the longest carbon chain with the OH group, then number it to give the OH group the lowest number.
- When naming ethers, both alkyl groups should be named and arranged alphabetically; for symmetrical ethers, add the prefix -di.
Properties and Interactions
- Alcohols and ethers are derivatives of water formed by replacing hydrogen atoms on the oxygen.
- Alcohols, ethers, and epoxides exhibit dipole-dipole interactions, while alcohols can also form hydrogen bonds.
- Alcohols are more polar compared to ethers and epoxides, impacting their solubility and boiling points.
Solubility and Boiling Points
- Compounds with 5 or fewer carbon atoms are water-soluble; those with more than 5 are organic-soluble only.
- The boiling point of alcohols, ethers, and epoxides can be increased by enhancing intermolecular forces and hydrogen bonding.
Synthesis and Reactions
- Alcohols and ethers can be synthesized via nucleophilic substitution reactions with alkyl halides, favoring strong nucleophiles and primary halides for optimal yield.
- Williamson Ether Synthesis involves the reaction of alkoxide ions with alkyl halides to form ethers.
- Unsymmetrical ethers are synthesized preferably using less sterically hindered halides.
Dehydration and Elimination Reactions
- Dehydration involves the elimination of OH and H, moving to create alkenes, where the most substituted alkene is the major product.
- For 2° and 3° alcohols, the E1 mechanism is followed, while 1° alcohols undergo the E2 mechanism.
Carbocation Rearrangements
- Carbocation rearrangement can occur in reactions involving 2° and 3° alcohols to form more stable carbocations.
Reactions with Acids
- Alcohols convert to better leaving groups by reacting with strong acids like HCl or H2SO4.
- The mechanism for converting primary alcohols involves an SN2 pathway, resulting in inversion of configuration, while 3° alcohols form a racemic mixture via SN1 mechanism.
Rearrangement and Reactions of Ethers
- Ethers react with strong acids to generate two nucleophilic substitution reactions, breaking C-O bonds.
- Thiols and sulfides serve as sulfur analogues to alcohols and ethers, respectively.
Nucleophilic Attack on Epoxides
- Nucleophilic attack on epoxides involves opening a three-membered ring structure, often at the less substituted carbon atom in unsymmetrical epoxides.
- The reaction mechanism typically follows SN2 pathways with strong nucleophiles leading to ring-opening.
Summary and Conclusion
- A comprehensive understanding of alcohols, ethers, and epoxides involves their structures, physical properties, naming conventions, synthesis routes, and distinctive reactivity patterns.
- Mastery of these concepts is essential for navigating organic chemistry topics effectively.
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