Organic Chemistry Alcohols Quiz
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Questions and Answers

Which statement accurately describes the difference between alcohols and phenols?

  • Alcohols lack a carbon backbone, while phenols have one.
  • Alcohols contain hydroxyl groups attached to alkyl groups, whereas phenols have hydroxyl groups attached to aromatic rings. (correct)
  • The -OH group in alcohols is attached to an aromatic ring, while in phenols it is attached to an alkyl group.
  • Phenols cannot be classified as primary, secondary, or tertiary, while alcohols can.
  • Which of the following compounds is classified as a secondary alcohol?

  • CH₃CH₂OH
  • CH₃CHOHCH₃ (correct)
  • C₆H₅CH₂OH
  • HOCH₂CH₂OH
  • What characterizes a benzylic alcohol?

  • The -OH group is directly bonded to a benzene ring.
  • The -OH group is attached to a carbon adjacent to an alkene.
  • The -OH group is part of a cyclic structure.
  • The -OH group is attached to a carbon next to a carbon that is part of a benzene ring. (correct)
  • Which type of alcohol contains more than two -OH groups?

    <p>Polyhydric Alcohol (A)</p> Signup and view all the answers

    Which of the following is an example of a vinylic alcohol?

    <p>CH₂=CHOH (A)</p> Signup and view all the answers

    Which method of preparation produces a tertiary alcohol when reacting with a ketone?

    <p>Grignard reagent reaction (B)</p> Signup and view all the answers

    What is the expected product when an alkene undergoes hydroboration-oxidation?

    <p>Secondary alcohol in an anti-Markovnikov manner (D)</p> Signup and view all the answers

    Which of the following reagents can reduce an aldehyde to a primary alcohol?

    <p>Sodium borohydride (B)</p> Signup and view all the answers

    Which of the following correctly describes the outcome of the reaction between a Grignard reagent and formaldehyde?

    <p>Produces a primary alcohol (D)</p> Signup and view all the answers

    In the reduction of ketones using lithium aluminum hydride, what type of alcohol is formed?

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

    What is the correct IUPAC name for vinyl alcohol?

    <p>Ethen-1-ol (B)</p> Signup and view all the answers

    Which of the following alcohols is a trihydric alcohol?

    <p>Glycerol (B)</p> Signup and view all the answers

    What distinguishes tert-butyl alcohol from other butyl alcohols?

    <p>It has a branched structure. (D)</p> Signup and view all the answers

    Which structural formula corresponds to 2,2-Dimethylpropan-1-ol?

    <p>$CH_3-C(CH_3)_2-CH_2-OH$ (B)</p> Signup and view all the answers

    What is the IUPAC name for the alcohol with the structural formula $CH_3-CH(OH)-CH(CH_3)-CH_3$?

    <p>3-Methylbutan-2-ol (B)</p> Signup and view all the answers

    Which of the following statements correctly describes the bond characteristics of phenol compared to methanol?

    <p>The C-O bond length in phenol is shorter than in methanol. (B)</p> Signup and view all the answers

    What is the correct classification for pyrogallol based on its structure?

    <p>Trihydric phenol (C)</p> Signup and view all the answers

    Which of the following methyl phenols is known as o-Cresol?

    <p>2-Methylphenol (D)</p> Signup and view all the answers

    Which structural feature distinguishes the bond angles in phenol from those in alcohols like methanol?

    <p>Higher sp2 hybridization in the carbon adjacent to oxygen in phenol. (A)</p> Signup and view all the answers

    Which of the following statements best describes the polarity of the O-H and C-O bonds in phenols?

    <p>Both bonds are polar because of oxygen's electronegativity. (A)</p> Signup and view all the answers

    What primarily contributes to the higher boiling points of alcohols compared to alkanes?

    <p>Formation of hydrogen bonds (A)</p> Signup and view all the answers

    Which factor is responsible for the decreasing solubility of alcohols in water as molecular mass increases?

    <p>Increasing prevalence of non-polar alkyl groups (C)</p> Signup and view all the answers

    Which statement correctly describes the relationship between alcohol structure and boiling points?

    <p>Primary alcohols consistently exhibit the highest boiling points (D)</p> Signup and view all the answers

    What effect do electron donating groups have on the acidity of alcohols?

    <p>Reduce the polarity of the O-H bond (B)</p> Signup and view all the answers

    How does branching in an alcohol chain affect its solubility in water?

    <p>It increases solubility by reducing non-polar surface area (C)</p> Signup and view all the answers

    What is the product of the reaction between ethyl alcohol and hydrogen halide?

    <p>Ethyl chloride (A)</p> Signup and view all the answers

    Which reaction type involves converting an alcohol and a carboxylic acid into an ester and water?

    <p>Esterification (B)</p> Signup and view all the answers

    What is the correct order of reactivity for alcohols undergoing cleavage of the C–O bond?

    <p>3° alcohol &gt; 2° alcohol &gt; 1° alcohol (A)</p> Signup and view all the answers

    In the dehydration of isopropyl alcohol, what is the main product formed?

    <p>Propene (A)</p> Signup and view all the answers

    What is the result of the reaction of alcohol with thionyl chloride?

    <p>Alkyl chloride and sulfur dioxide (D)</p> Signup and view all the answers

    What is the final product of a 1° alcohol after complete oxidation?

    <p>Carboxylic acid (C)</p> Signup and view all the answers

    Which alcohol does not undergo oxidation under normal conditions?

    <p>3° alcohol (C)</p> Signup and view all the answers

    Which reagent is required for the dehydrogenation of a 2° alcohol to a ketone?

    <p>Cu at 573 K (D)</p> Signup and view all the answers

    What is expected as a product when tertiary alcohols are dehydrated?

    <p>Alkene (C)</p> Signup and view all the answers

    In the oxidation of a 2° alcohol, which step occurs first?

    <p>Formation of ketone (D)</p> Signup and view all the answers

    What is the primary reaction condition for producing phenol from chlorobenzene?

    <p>623 K, 320 atm (B)</p> Signup and view all the answers

    Which mechanism explains the increased acidity of phenols in the presence of electron-withdrawing groups?

    <p>Enhanced delocalization of the negative charge at ortho and para positions (A)</p> Signup and view all the answers

    What is the byproduct formed when cumene undergoes oxidation to produce phenol?

    <p>Cumene hydroperoxide (C)</p> Signup and view all the answers

    What effect do electron-donating groups have on the acidity of phenol?

    <p>Decrease acidity by blocking the formation of the phenoxide ion (D)</p> Signup and view all the answers

    What is produced when aniline is treated with sodium nitrite and hydrochloric acid?

    <p>Benzene diazonium chloride (C)</p> Signup and view all the answers

    Which product results from the acetylation reaction of phenol?

    <p>Phenyl acetate (A)</p> Signup and view all the answers

    What reagent is used in the nitration of aniline to form o-nitrophenol?

    <p>dil. HNO3 (D)</p> Signup and view all the answers

    During the bromination of phenol, what is the major product formed?

    <p>p-bromophenol (C)</p> Signup and view all the answers

    What is the primary reagent needed to convert phenyl benzoate into aniline?

    <p>Zn, NH3 (A)</p> Signup and view all the answers

    What combination of reagents and conditions leads to the formation of p-nitrophenol from aniline?

    <p>conc. HNO3 and conc. H2SO4 (B)</p> Signup and view all the answers

    Which product is formed from the oxidation of 2,4,6-Tribromophenol?

    <p>Benzoquinone (B)</p> Signup and view all the answers

    Which reaction condition is specifically used for the bromination of phenol?

    <p>Br2 in CS2 at 273 K (C)</p> Signup and view all the answers

    What are the reactants in the benzoylation reaction involving phenol?

    <p>Phenol and C6H5COCl (A)</p> Signup and view all the answers

    Flashcards

    Primary Alcohol

    An alcohol where the -OH group is attached to a primary carbon atom.

    Monohydric Alcohol

    An alcohol containing only one -OH group.

    Phenol

    An aromatic compound with an -OH group attached to an aromatic ring (like benzene).

    Secondary Alcohol

    An alcohol where the -OH group is attached to a secondary carbon atom.

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    Dihydric Alcohol

    An alcohol containing two -OH groups.

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    IUPAC naming of alcohols

    Alcohols are named in the IUPAC system by identifying the longest carbon chain containing the hydroxyl (-OH) group, numbering the carbon atoms to place the hydroxyl group at the lowest possible position, and adding the suffix -ol to the alkane name.

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    Naming dihydric alcohols

    Dihydric alcohols (alcohols with two hydroxyl groups) are named as alkanediols in the IUPAC system.

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    Naming trihydric alcohols

    Trihydric alcohols (alcohols with three hydroxyl groups) are named as alkanetriols in the IUPAC system.

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    Ethyl alcohol IUPAC name

    Ethanol

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    n-Butyl alcohol IUPAC name

    Butan-1-ol

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    Phenol structure

    The simplest hydroxy derivative of benzene, with a hydroxyl group (-OH) attached to a benzene ring.

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    Methyl Phenols (Cresols)

    Phenols with a methyl group (-CH3) substituted on the benzene ring. They are named as a derivative of phenol.

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    Dihydric/Trihydric Phenols

    Phenols that have two or three hydroxyl groups (-OH) on the benzene ring respectively.

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    C-O Bond Angle in Phenol

    Slightly less than the tetrahedral angle (109°28′) due to repulsion between the lone pairs of electrons on the oxygen atom.

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    Phenol C-O Bond Length

    Shorter than in methanol due to conjugation with the aromatic ring and sp2 hybridization of the carbon.

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    Alcohol preparation from alkenes (acid-catalyzed hydration)

    Adding water to an alkene using an acid catalyst, following Markovnikov's rule, to create an alcohol.

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    Alcohol preparation from alkenes (hydroboration-oxidation)

    Adding water to an alkene in an anti-Markovnikov fashion, through hydroboration and oxidation.

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    Alcohol preparation from aldehydes/ketones using metal hydrides

    Reducing aldehydes and ketones to alcohols using metal hydrides like LiAlH₄ or NaBH₄.

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    Grignard reagent reaction with aldehydes/ketones/formaldehyde for alcohols

    Grignard reagents react with carbonyl compounds (formaldehyde, aldehydes, and ketones) producing primary, secondary, and tertiary alcohols, respectively.

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    Markovnikov's rule

    When an alkene reacts with an acid-catalyzed addition reaction, the hydrogen atom adds to the less substituted carbon.

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    Boiling Point: Alcohols vs. Alkanes

    Alcohols have significantly higher boiling points than comparable alkanes because of strong intermolecular hydrogen bonding.

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    Boiling Point Trend: Isomeric Alcohols

    Primary alcohols have the highest boiling points followed by secondary and then tertiary alcohols. This is due to decreasing surface area with increasing branching in the alkyl group.

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    Solubility: Alcohols & Water

    Lower molecular weight alcohols are soluble in water because they can form hydrogen bonds with water molecules. Solubility decreases with increasing molecular mass due to the non-polar alkyl group becoming dominant.

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    Alcohols: Nucleophile or Electrophile?

    Alcohols can act as both nucleophiles and electrophiles, depending on the reaction conditions.

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    Alcohol Acidity Trend

    Electron-releasing alkyl groups increase electron density on the oxygen atom in alcohols, decreasing the polarity of the O-H bond and making the alcohol less acidic.

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    Oxidation of 1° Alcohol

    1° alcohols are oxidized to aldehydes, which are further oxidized to carboxylic acids, both with the same number of carbon atoms.

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    Oxidation of 2° Alcohol

    2° alcohols are oxidized to ketones by reagents like CrO₃.

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    Why 3° Alcohols Don't Oxidize?

    3° alcohols don't readily oxidize because they lack the necessary alpha-hydrogen atoms.

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    Dehydrogenation of Alcohols

    Removing hydrogen from alcohols using a catalyst like Cu at 573 K.

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    Dehydrogenation of 3° Alcohol

    3° alcohols undergo dehydration to alkenes using Cu at 573 K.

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    Alcohol Reactivity with Metals

    Alcohols react with metals like sodium and aluminum, producing alkoxides and hydrogen gas. The reaction is exothermic and often used to prepare alkoxides, which are important reagents in organic synthesis.

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    Esterification

    The process of forming an ester from an alcohol and a carboxylic acid, acid anhydride, or acyl chloride. It involves the elimination of water and results in the formation of a new C-O bond.

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    Cleavage of C-O Bond in Alcohols

    The breaking of the C-O bond in alcohols can be influenced by the alcohol's structure. Tertiary alcohols are most easily cleaved, followed by secondary and then primary alcohols.

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    Reaction with Hydrogen Halides (HX)

    Alcohols react with hydrogen halides like HCl to form alkyl halides and water. The reaction proceeds via an SN1 or SN2 mechanism, depending on the structure of the alcohol.

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    Dehydration of Alcohols

    The elimination of water from an alcohol molecule to generate an alkene. Tertiary alcohols dehydrate most readily, followed by secondary and then primary alcohols.

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    Phenol Preparation: From Aryl Halides

    Phenol can be synthesized from aryl halides, like chlorobenzene, by reacting with NaOH under high temperature and pressure. This process involves a nucleophilic substitution reaction.

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    Phenol Preparation: From Benzenesulfonic Acid

    Phenol can be obtained by oxidizing benzenesulfonic acid using strong oxidizing agents. The process involves the removal of the sulfonic acid group and the formation of phenol.

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    Phenol Preparation: From Diazonium Salts

    Phenol can be prepared from diazonium salts through a two-step process. First, aniline is reacted with sodium nitrite and hydrochloric acid to form benzene diazonium chloride. The second step involves treating the salt with water to form phenol and release nitrogen gas.

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    Phenol Acidity: How does it compare to other alcohols?

    Phenol is more acidic than regular alcohols due to the stabilization of the phenoxide ion through resonance delocalization of the negative charge. This delocalization distributes the charge over the entire benzene ring.

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    Phenol Acidity: Effect of Substituents

    The acidity of phenol is affected by substituents on the benzene ring. Electron-withdrawing groups increase acidity by further stabilizing the phenoxide ion through further delocalization. Electron-donating groups decrease acidity by hindering delocalization.

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    Phenol Acetylation

    A reaction where phenol is reacted with acetyl chloride (CH3COCl) in the presence of pyridine to form phenyl acetate and hydrochloric acid (HCl).

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    Phenol Benzoylation

    A reaction where phenol reacts with benzoyl chloride (C6H5COCl) in the presence of sodium hydroxide (NaOH) to form phenyl benzoate and hydrochloric acid (HCl).

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    What is the product of reducing phenyl benzoate?

    Reduction of phenyl benzoate using zinc and ammonia (Zn, NH3) with zinc chloride (ZnCl2) at 675 K produces aniline and zinc oxide (ZnO).

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    Nitration of Aniline

    The reaction of aniline with dilute nitric acid (dil. HNO3) produces o-nitrophenol, also known as 2-nitrophenol.

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    Nitration of Aniline (Concentrated)

    The reaction of aniline with concentrated nitric acid (conc. HNO3) and concentrated sulfuric acid (conc. H2SO4) produces p-nitrophenol, also known as 4-nitrophenol.

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    Bromination of Phenol

    The reaction of phenol with bromine (Br2) in carbon disulfide (CS2) at 273 K produces p-bromophenol (major product), o-bromophenol, and hydrogen bromide (HBr).

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    Tribromophenol Formation

    p-Bromophenol reacts with aqueous bromine (3Br2(aq)) to produce 2,4,6-tribromophenol and hydrogen bromide (3HBr).

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    Oxidation of Tribromophenol

    2,4,6-Tribromophenol is oxidized by potassium dichromate and sulfuric acid (K2Cr2O7/H2SO4) to produce benzoquinone and water (H2O).

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