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Questions and Answers

What is the structural formula for 1-methylpropyl?

  • - CH(CH3)CH(CH3)
  • - CH(CH3)CH2CH3 (correct)
  • - CCH3
  • - CH2CH2CH3

    • Which name corresponds to the structural formula - CH3?

  • butyl
  • propyl
  • methyl (correct)
  • ethyl

    • What is the condensed structural formula for 2-methylpropyl?

  • - CH(CH3)CH2CH3 (correct)
  • - C(CH3)2CH2
  • - CH3CHCH3
  • - CH2(CH3)2

    • Identify the structural formula for tert-butyl.

    <ul> <li>C(CH3)3</li> </ul> Signup and view all the answers

    Which of the following represents the condensed formula for propyl?

    <ul> <li>CH2CH2CH3</li> </ul> Signup and view all the answers

    What does Zaitsev’s rule state regarding hydrogen atom loss during intramolecular alcohol dehydration?

    <p>Hydrogen loss occurs from the carbon adjacent to the hydroxyl-bearing carbon with the fewest hydrogen atoms.</p> Signup and view all the answers

    At what temperature does intermolecular alcohol dehydration typically occur for primary alcohols?

    <p>140°C</p> Signup and view all the answers

    What is the product of intermolecular alcohol dehydration?

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

    Which statement is true regarding the behavior of secondary and tertiary alcohols during dehydration?

    <p>They always yield alkene products.</p> Signup and view all the answers

    What is the preferred alkene product formed from dehydration of 2-butanol?

    <p>2-butene</p> Signup and view all the answers

    What type of reaction is described in the dehydration of alcohols?

    <p>Condensation reaction</p> Signup and view all the answers

    Why is Zaitsev's rule particularly useful when predicting product formation in alcohol dehydration?

    <p>It helps identify the preferred carbon for hydrogen loss.</p> Signup and view all the answers

    Which of the following statements is incorrect regarding the reactions of alcohols?

    <p>Primary alcohols usually produce alkenes rather than ethers when dehydrated.</p> Signup and view all the answers

    What is the correct suffix added to the name of a hydrocarbon group attached to the oxygen atom in an ether when both groups are identical?

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

    Which of the following correctly represents the IUPAC naming convention for ethers?

    <p>The base name is derived from the longest carbon chain.</p> Signup and view all the answers

    What change is made to the hydrocarbon group's name when it becomes an alkoxy group?

    <p>The '-yl' ending is replaced with '-oxy'.</p> Signup and view all the answers

    Which ether can exhibit constitutional isomerism?

    <p>C4 ether</p> Signup and view all the answers

    In the case of the ether named '2-Ethoxybutane', what does 'ethoxy' indicate?

    <p>It indicates the presence of a two-carbon alkyl group attached to the base chain.</p> Signup and view all the answers

    What is a necessary consideration when determining constitutional isomerism in ethers?

    <p>The partitioning of carbon atoms between the two alkyl groups.</p> Signup and view all the answers

    What is the main characteristic that distinguishes thiols from alcohols and ethers?

    <p>Thiols have stronger characteristic odors.</p> Signup and view all the answers

    What is the typical state of dimethyl sulfide at room temperature?

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

    Which of the following correctly names a compound with both ethyl and methyl groups attached to oxygen?

    <p>Ethyl methyl ether</p> Signup and view all the answers

    What is the minimum number of carbon atoms needed in an ether for constitutional isomerism to be possible?

    <p>4 carbon atoms</p> Signup and view all the answers

    Which of the following is true about thioethers?

    <p>They use sulfide in place of ether in common names.</p> Signup and view all the answers

    Which compounds are typically produced by bacteria in the mouth that contribute to 'morning breath'?

    <p>Hydrogen sulfide and dimethyl sulfide</p> Signup and view all the answers

    What type of bond is weaker than a carbon-oxygen bond?

    <p>Carbon-sulfur</p> Signup and view all the answers

    What do garlic and onions have in common regarding their sulfur-containing compounds?

    <p>Many sulfur-containing compounds formed are common to both garlic and onions.</p> Signup and view all the answers

    What is the perception of the smell of fried onions?

    <p>Considered pleasant by most people.</p> Signup and view all the answers

    How are thiols and thioethers alike in terms of chemical properties?

    <p>Both exhibit functional group isomerism.</p> Signup and view all the answers

    Which of the following types of isomerism is possible for alcohols with three or more carbon atoms?

    <p>Constitutional isomerism</p> Signup and view all the answers

    Methanol is commonly referred to as which of the following?

    <p>Wood alcohol</p> Signup and view all the answers

    What is the main toxic byproduct produced when methanol is oxidized by alcohol dehydrogenase in the body?

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

    What substance is used to treat methanol poisoning by inhibiting its oxidation?

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

    Which alcohol is produced from the fermentation of grains such as corn and barley?

    <p>Ethyl alcohol</p> Signup and view all the answers

    What is the maximum concentration of ethanol that can be produced through yeast fermentation?

    <p>18%</p> Signup and view all the answers

    Methyl alcohol is primarily produced today through which of the following reactions?

    <p>Reaction between H2 and CO</p> Signup and view all the answers

    Which statement about ethanol's concentration during fermentation is true?

    <p>It maximizes at about 18% due to yeast inactivation.</p> Signup and view all the answers

    Why do alcohols have higher boiling points than alkanes of similar molecular mass?

    <p>Alcohols can form hydrogen bonds.</p> Signup and view all the answers

    How are alcohols primarily prepared from alkenes?

    <p>By hydration reactions in the presence of sulfuric acid.</p> Signup and view all the answers

    What is the classification of a primary alcohol?

    <p>One hydroxyl group and a carbon atom bonded to only one other carbon atom.</p> Signup and view all the answers

    What does Markovnikov's rule help to determine?

    <p>The predominant alcohol product from alkene reactions.</p> Signup and view all the answers

    What feature differentiates tertiary alcohols from other types?

    <p>They have a hydroxyl group attached to a carbon bonded to three other carbons.</p> Signup and view all the answers

    Which of the following statements about the solubility of alcohols is true?

    <p>Alcohols have much higher solubility in water than alkanes of similar molecular mass.</p> Signup and view all the answers

    In the process of adding H2 to a carbonyl group, what is the result?

    <p>Addition of hydrogen to both the carbon and oxygen atoms.</p> Signup and view all the answers

    Which type of alcohol is characterized by the hydroxyl group connected to a carbon bonded to two other carbons?

    <p>Secondary alcohol (2o)</p> Signup and view all the answers

    Study Notes

    General, Organic, and Biological Chemistry - Chapter 14

    • Chapter covers Alcohols, Phenols, and Ethers

    Chapter 14 - Table of Contents

    • 14.1 Bonding Characteristics of Oxygen Atoms in Organic Compounds
    • 14.2 Structural Characteristics of Alcohols
    • 14.3 Nomenclature for Alcohols
    • 14.4 Isomerism for Alcohols
    • 14.5 Important Commonly Encountered Alcohols (e.g., Methanol, Ethanol, Isopropyl Alcohol)
    • 14.6 Physical Properties of Alcohols
    • 14.7 Preparation of Alcohols
    • 14.8 Classification of Alcohols (primary, secondary, tertiary)
    • 14.9 Chemical Reactions of Alcohols (combustion, intramolecular dehydration, oxidation, halogenation)
    • 14.10 Polymeric Alcohols
    • 14.11 Structural Characteristics of Phenols
    • 14.12 Nomenclature for Phenols
    • 14.13 Physical and Chemical Properties of Phenols (acidity)
    • 14.14 Occurrence of and Uses for Phenols (antiseptic, antioxidant properties)
    • 14.15 Structural Characteristics of Ethers
    • 14.16 Nomenclature for Ethers
    • 14.17 Isomerism for Ethers
    • 14.18 Physical and Chemical Properties of Ethers (flammability, uses as anesthetics)
    • 14.19 Cyclic Ethers
    • 14.20 Sulfur Analogs of Alcohols (thiols, properties)
    • 14.21 Sulfur Analogs of Ethers (thioethers, properties)

    Section 14.1 - Bonding Characteristics of Oxygen Atoms in Organic Compounds

    • Oxygen is a Group VIA element
    • Has 6 valence electrons
    • Has two lone pairs
    • Can form two covalent bonds (two single bonds or one double bond)

    Section 14.2 - Structural Characteristics of Alcohols

    • A hydroxyl (-OH) group bonded to a saturated carbon atom constitutes an alcohol
    • General structure: R-OH
    • Examples: CH3OH, C3H7OH

    Section 14.3 - Nomenclature for Alcohols (Common Names)

    • For C1-C4 alkyl groups, name all carbon atoms as a single alkyl group (methyl, ethyl, propyl, butyl)
    • Add the word "alcohol"

    Section 14.4 - Isomerism for Alcohols

    • Constitutional isomerism is possible for alcohols with 3 or more carbon atoms
    • Two types of isomers: Skeletal and positional isomers

    Section 14.5 - Important Commonly Encountered Alcohols

    • Methanol: A good fuel and solvent; formerly produced by heating wood; toxic, can cause blindness.
    • Ethanol: Grain alcohol; prepared from yeast fermentation of plant sugars; excellent solvent and fuel; toxic effects include hangover.
    • Isopropyl Alcohol: Three-carbon alcohol; used as rubbing alcohol; toxic, faster elimination, and may induce vomiting

    Section 14.6 - Physical Properties of Alcohols

    • Alcohol molecules exhibit both polar and nonpolar character
    • Boiling points tend to increase with the length of the carbon chain
    • Small monohydroxy alcohols are completely soluble in water
    • Solubility decreases beyond three carbons (longer chains)

    Section 14.7 - Preparation of Alcohols

    • Prepared by hydration of alkenes
    • Alkenes react with water in presence of sulfuric acid
    • Markovnikov's rule is used to predict predominant alcohol product

    Section 14.8 - Classification of Alcohols

    • Primary alcohol (1°): Hydroxyl group attached to one other carbon atom
    • Secondary alcohol (2°): Hydroxyl group attached to two other carbon atoms
    • Tertiary alcohol (3°): Hydroxyl group attached to three other carbon atoms

    Section 14.9 - Chemical Reactions of Alcohols

    • Combustion: Produces carbon dioxide and water
    • Intramolecular Dehydration: Removing water (-H and -OH) from a single molecule to form an alkene (Zaitsev's rule applies to predict the predominant product)
    • Oxidation: Increasing C-O bonds and/or decreasing C-H bonds (primary alcohols yield aldehydes, then carboxylic acids; secondary alcohols yield ketones; tertiary alcohols do not react)
    • Halogenation: Substituting a halogen atom for the hydroxyl group to form an alkyl halide

    Section 14.10 - Polymeric Alcohols

    • Synthesis of polymeric alcohols with structures similar to substituted polyethylenes
    • Polyvinyl alcohol (PVA) is a tough, water-soluble polymer with uses in films, tubes, and fibers

    Section 14.11 - Structural Characteristics of Phenols

    • Phenol: An -OH group attached to an aromatic ring
    • Aryl group: Aromatic carbon ring system where one hydrogen has been removed
    • General formula for aryl alcohol: Ar-OH

    Section 14.12 - Nomenclature for Phenols

    • Name "phenol” and indicate position of substituent with a number followed by the name

    Section 14.13 - Physical and Chemical Properties of Phenols

    • Phenols are usually low-melting solids or liquids at room temp
    • Sparingly soluble in water
    • Many phenols have antiseptic and disinfectant properties
    • Phenol itself is a simple phenol, a colorless solid with a medicinal odor with a melting point of 41°C and greater water solubility than other phenols
    • Phenols are weak acids in solution

    Section 14.14 - Occurrence of and Uses for Phenols

    • Many phenols (e.g., 4-hexylresorcinol, o-phenylphenol, 2-benzyl-4-chlorophenol) have antiseptic properties
    • Some phenols have antioxidant properties (e.g., BHA, BHT, Vitamin E) & as flavoring agents and/or antibacterials

    Section 14.15 - Structural Characteristics of Ethers

    • Ethers: An oxygen atom bonded to two carbon atoms
    • General formula: R—O—R

    Section 14.16 - Nomenclature for Ethers

    • Name the two hydrocarbon groups and the word "ether"
    • List the hydrocarbon groups alphabetically
    • Use "di" if both hydrocarbon groups are the same

    Section 14.17 - Isomerism for Ethers

    • Ethers with greater than two alkyl groups exhibit constitutional isomerism
    • Isomers: Different arrangements of the atoms in the molecule for the same molecular formula
    • C2 and C3 ethers do not exhibit constitutional isomerism

    Section 14.18 - Physical and Chemical Properties of Ethers

    • Boiling points are similar to alkanes of the same molecular mass

    Section 14.19 - Cyclic Ethers

    • Cyclic ethers contain the ether functional group as part of a ring system (heterocyclic organic compounds)

    Section 14.20 - Sulfur Analogs of Alcohols (Thiols)

    • Thiols (R-SH): Sulfur analogue of alcohols
    • Lower boiling point than corresponding alcohol due to lack of hydrogen bonding
    • Strong unpleasant odor

    Section 14.21 - Sulfur Analogs of Ethers (Thioethers)

    • Thioethers (R-S-R): Sulfur analogue of ethers
    • Less reactive than alcohols and ethers.
    • Exhibit functional-group isomerism like alcohols and ethers

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