Questions and Answers
What do alcohols, epoxides, and ethers have in common?
What do alcohols contain?
A hydroxy group (OH) bonded to a sp3 hybridized carbon.
What do enols contain?
An OH group on a sp2 hybridized carbon of a C-C double bond.
What do phenols contain?
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What is an ether characterized by?
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A symmetrical ether has two different alkyl groups.
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Both alcohols and ethers are organic derivatives of H2O.
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What is an epoxide?
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What is the hybridization of oxygen in alcohols, ethers, and epoxides?
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The bond angle around the O in an alcohol and ether is ____.
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The C-O-C bond angle of an epoxide is ____.
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What suffix is used to identify alcohols in the IUPAC system?
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When an OH group is bonded to a ring, the ring is numbered ending with the OH group.
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What are the two steps in naming an alcohol according to IUPAC?
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How do you assign simple alcohols a 'common name'?
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What are diols or glycols?
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What are triols?
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How do you name simple ethers?
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How do you name a complex ether?
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What are the three ways to name an epoxide?
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How do you name an epoxide as an epoxyalkane?
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How do you name an epoxide as an oxirane?
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How do you name an epoxide as an alkene oxide?
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What interactions do alcohols, ethers, and epoxides exhibit?
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Alcohols are much more polar than ethers and epoxides.
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Increasing the number of R groups around the carbon bonded to OH does what to the extent of hydrogen bonding?
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What are two ways to increase the boiling point of alcohols, ethers, and epoxides?
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Determine the solubility conditions for alcohols, ethers, and epoxides:
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In the host-guest complex known as the crown ether-cation complex, who is the host and who is the guest?
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What is molecular recognition?
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Alcohols and ethers are common products of what reaction?
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Alcohols and ethers are synthesized from alkyl halides in what type of reactions?
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What is the Williamson Ether Synthesis?
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Which path is preferred for synthesizing unsymmetrical ethers?
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What type of nucleophile is needed to synthesize an alcohol?
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What type of salt is needed to make an ether?
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A halohydrin can perform what type of reaction to form an epoxide?
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Alcohols and alkyl halides both contain good leaving groups.
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Why does nucleophilic substitution with ROH not work?
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What must happen for an alcohol to undergo a substitution reaction?
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When the alcohol is treated with a strong acid, what does the -OH get converted to?
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What is dehydration?
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As the substitution of an alcohol increases, what happens to the rate of dehydration?
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What product is considered the major product in dehydration reactions?
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What elimination mechanism do 2° & 3° alcohols undergo?
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What elimination mechanism do 1° alcohols undergo?
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What are the three steps of a 2°/3° alcohol dehydration?
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What are the two steps of a 1° alcohol dehydration?
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What is Le Châtelier's Principle?
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What is carbocation rearrangement?
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What are the four steps of a 1,2 methyl shift in dehydration?
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In dehydration reactions, what happens when POCl3 is used?
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What is the Protonation of OH from 1° form?
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What is the Protonation of OH from 2° and 3° form?
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What affects the reactivity of hydrogen halide?
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What Lewis acid catalyst is used when 1° alcohols react with HCl?
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What kind of stereochemistry do 1° alcohols react in SN2 reaction to form?
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What do 3° alcohols yield when reacting in an SN1 Mechanism?
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Carbocation rearrangement is possible in the SN1 reactions of 2° and 3° alcohols.
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What does SOCl2 convert 1° and 2° alcohols into?
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What does PBr3 convert alcohols into?
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Summarize converting ROH to RX.
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Alcohols are converted to alkyl tosylates by treatment of...
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Since alkyl tosylates have good leaving groups, they undergo...
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Summarize the two-step reaction of an alcohol with TsCl and pyridine.
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Summarize nucleophilic substitution and β elimination of alcohols.
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The leaving groups of ethers can only be converted to good leaving groups by reaction of which strong acids?
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Since both C-O bonds are broken in an ether, what occurs?
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The 2° or 3° alkyl groups of an ether oxygen are cleaved by what mechanism?
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Methyl or 1° alkyl groups are cleaved by what mechanism?
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In the mechanism of an ether with a strong acid HX, what is the first step?
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In the mechanism of an ether with a strong acid HX, what is the second step?
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Thiols and sulfides are sulfur analogues of what?
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What happens during nucleophilic attack on an epoxide?
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What are the two steps to opening an epoxide ring with a strong nucleophile?
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What type of mechanism do strong nucleophiles like -OH, -OR, -CN, -SR, and NH3 use when reacting with epoxides?
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In an unsymmetrical epoxide, where does the nucleophile attack?
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If the epoxide is symmetrical, nucleophilic attack occurs from where?
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What are the two steps in the opening of an epoxide ring with H-Z?
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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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Test your knowledge of key concepts in Organic Chemistry Chapter 9 with these flashcards. This chapter covers important functional groups such as alcohols, epoxides, ethers, and phenols. Study the definitions and properties to enhance your understanding of organic compounds.