Organic Chemistry Chapter 9 Flashcards
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Questions and Answers

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?

    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?

    <p>An OH group on a benzene ring.</p> Signup and view all the answers

    What is an ether characterized by?

    <p>Contains 2 alkyl groups bonded to an oxygen atom.</p> Signup and view all the answers

    A symmetrical ether has two different alkyl groups.

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

    Both alcohols and ethers are organic derivatives of H2O.

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

    What is an epoxide?

    <p>An ether having the oxygen atom in a three-membered ring.</p> Signup and view all the answers

    What is the hybridization of oxygen in alcohols, ethers, and epoxides?

    <p>sp3 hybridized.</p> Signup and view all the answers

    The bond angle around the O in an alcohol and ether is ____.

    <p>109.5°</p> Signup and view all the answers

    The C-O-C bond angle of an epoxide is ____.

    <p>60°</p> Signup and view all the answers

    What suffix is used to identify alcohols in the IUPAC system?

    <p>-ol</p> Signup and view all the answers

    When an OH group is bonded to a ring, the ring is numbered ending with the OH group.

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

    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?

    <p>Compounds with two OH groups.</p> Signup and view all the answers

    What are triols?

    <p>Compounds with three OH groups.</p> Signup and view all the answers

    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?

    <p>Dipole-dipole interactions.</p> Signup and view all the answers

    Alcohols are much more polar than ethers and epoxides.

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

    Increasing the number of R groups around the carbon bonded to OH does what to the extent of hydrogen bonding?

    <p>Decreases.</p> Signup and view all the answers

    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:

    <p>Having &lt;= 5C's = H2O soluble Having &gt; 5C's = H2O insoluble</p> Signup and view all the answers

    In the host-guest complex known as the crown ether-cation complex, who is the host and who is the guest?

    <p>The crown ether is the host and the cation is the guest.</p> Signup and view all the answers

    What is molecular recognition?

    <p>The ability of a host molecule to bind to a specific guest.</p> Signup and view all the answers

    Alcohols and ethers are common products of what reaction?

    <p>Nucleophilic substitution.</p> Signup and view all the answers

    Alcohols and ethers are synthesized from alkyl halides in what type of reactions?

    <p>SN2 reactions using strong nucleophiles.</p> Signup and view all the answers

    What is the Williamson Ether Synthesis?

    <p>Formation of an ether from the reaction of an alkoxide ion with an alkyl halide.</p> Signup and view all the answers

    Which path is preferred for synthesizing unsymmetrical ethers?

    <p>The path that uses the less sterically hindered halide.</p> Signup and view all the answers

    What type of nucleophile is needed to synthesize an alcohol?

    <p>Hydroxide.</p> Signup and view all the answers

    What type of salt is needed to make an ether?

    <p>Alkoxide.</p> Signup and view all the answers

    A halohydrin can perform what type of reaction to form an epoxide?

    <p>Intramolecular reaction.</p> Signup and view all the answers

    Alcohols and alkyl halides both contain good leaving groups.

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

    Why does nucleophilic substitution with ROH not work?

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    What must happen for an alcohol to undergo a substitution reaction?

    <p>The OH group must first be converted into a better leaving group by reacting with a strong acid.</p> Signup and view all the answers

    When the alcohol is treated with a strong acid, what does the -OH get converted to?

    <p>H2O.</p> Signup and view all the answers

    What is dehydration?

    <p>A β elimination reaction where OH &amp; H are removed from the α &amp; β carbons respectively.</p> Signup and view all the answers

    As the substitution of an alcohol increases, what happens to the rate of dehydration?

    <p>The rate of dehydration increases.</p> Signup and view all the answers

    What product is considered the major product in dehydration reactions?

    <p>The most substituted alkene.</p> Signup and view all the answers

    What elimination mechanism do 2° & 3° alcohols undergo?

    <p>E1.</p> Signup and view all the answers

    What elimination mechanism do 1° alcohols undergo?

    <p>E2.</p> Signup and view all the answers

    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?

    <p>A system at equilibrium will react to counteract any disturbance to the equilibrium.</p> Signup and view all the answers

    What is carbocation rearrangement?

    <p>A less stable carbocation can rearrange to a more stable carbocation by shifting a hydrogen or alkyl group.</p> Signup and view all the answers

    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?

    <p>Converts a poor leaving group into a good leaving group.</p> Signup and view all the answers

    What is the Protonation of OH from 1° form?

    <p>RX by SN2 Mechanism.</p> Signup and view all the answers

    What is the Protonation of OH from 2° and 3° form?

    <p>RX by SN1 Mechanism.</p> Signup and view all the answers

    What affects the reactivity of hydrogen halide?

    <p>Increasing acidity.</p> Signup and view all the answers

    What Lewis acid catalyst is used when 1° alcohols react with HCl?

    <p>ZnCl2.</p> Signup and view all the answers

    What kind of stereochemistry do 1° alcohols react in SN2 reaction to form?

    <p>Inversion.</p> Signup and view all the answers

    What do 3° alcohols yield when reacting in an SN1 Mechanism?

    <p>Racemic mixture.</p> Signup and view all the answers

    Carbocation rearrangement is possible in the SN1 reactions of 2° and 3° alcohols.

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

    What does SOCl2 convert 1° and 2° alcohols into?

    <p>Alkyl chlorides.</p> Signup and view all the answers

    What does PBr3 convert alcohols into?

    <p>Alkyl bromides.</p> Signup and view all the answers

    Summarize converting ROH to RX.

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    Alcohols are converted to alkyl tosylates by treatment of...

    <p>p-toluenesulfonyl chloride in the presence of pyridine.</p> Signup and view all the answers

    Since alkyl tosylates have good leaving groups, they undergo...

    <p>Both nucleophilic substitution and beta elimination.</p> Signup and view all the answers

    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?

    <p>HBr or HI.</p> Signup and view all the answers

    Since both C-O bonds are broken in an ether, what occurs?

    <p>2 nucleophilic substitution reactions occur.</p> Signup and view all the answers

    The 2° or 3° alkyl groups of an ether oxygen are cleaved by what mechanism?

    <p>SN1 mechanism.</p> Signup and view all the answers

    Methyl or 1° alkyl groups are cleaved by what mechanism?

    <p>SN2 mechanism.</p> Signup and view all the answers

    In the mechanism of an ether with a strong acid HX, what is the first step?

    <p>HX protonates the oxygen to make it a good leaving group.</p> Signup and view all the answers

    In the mechanism of an ether with a strong acid HX, what is the second step?

    <p>HX provides a source of X- for substitution.</p> Signup and view all the answers

    Thiols and sulfides are sulfur analogues of what?

    <p>Alcohols and ethers respectively.</p> Signup and view all the answers

    What happens during nucleophilic attack on an epoxide?

    <p>Opens the strained three-membered ring.</p> Signup and view all the answers

    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?

    <p>SN2 mechanism.</p> Signup and view all the answers

    In an unsymmetrical epoxide, where does the nucleophile attack?

    <p>Less substituted carbon atom.</p> Signup and view all the answers

    If the epoxide is symmetrical, nucleophilic attack occurs from where?

    <p>The back side at either C-O forming a racemic mixture.</p> Signup and view all the answers

    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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    Description

    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.

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