Organic Chemistry: Carboxylic Acid Derivatives
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Questions and Answers

What is produced when Grignard reagents react with dry CO2?

  • Metal carboxylate (correct)
  • Alcohol
  • Alkyl halide
  • Acid anhydride

    • What is the outcome of hydrolyzing nitriles with acid or base catalysis?

  • Primary alcohols
  • Ester and water
  • Alkyl halides
  • Carboxylic acids and ammonia (correct)

    • Which reagent is used to convert carboxylic acids into acid chlorides?

  • SOCl2 (correct)
  • NaOH
  • HCl
  • H2O

    • How can acid anhydrides be formed from carboxylic acids?

    <p>Strong heating to remove water</p> Signup and view all the answers

    What kind of reaction pattern is exemplified by nucleophilic acyl substitution in carboxylic acid derivatives?

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

    What is the correct suffix used for naming carboxylic acids derived from open-chain alkanes?

    <p>-oic acid</p> Signup and view all the answers

    In the naming of nitriles, which of the following is true?

    <p>Nitriles are named by adding -nitrile to the alkane name.</p> Signup and view all the answers

    What characteristic bond angles are present in carboxylic acids due to sp2 hybridization?

    <p>120</p> Signup and view all the answers

    Which of the following statements correctly describes the solubility of carboxylic acids with more than six carbons?

    <p>They are only slightly soluble in water.</p> Signup and view all the answers

    How do electronegative substituents affect the formation of the carboxylate ion?

    <p>They promote its formation.</p> Signup and view all the answers

    Which of the following acids is NOT a stronger acid than acetic acid?

    <p>Propanoic acid</p> Signup and view all the answers

    What is the primary result when a carboxylic acid reacts with strong bases?

    <p>Production of metal carboxylate salts</p> Signup and view all the answers

    Which reagent is used for the oxidative cleavage of alkenes to form carboxylic acids?

    <p>KMnO4</p> Signup and view all the answers

    What is the primary reaction associated with carboxylic acid derivatives?

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

    How are acid halides named from their corresponding carboxylic acids?

    <p>By replacing -ic acid with -yl or specifying the halide</p> Signup and view all the answers

    Which carboxylic acid derivative is the least reactive due to its electrophilic nature?

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

    What reagent is commonly used to synthesize esters from carboxylic acids?

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

    Which process converts acid halides into carboxylic acids?

    <p>Hydrolysis with water</p> Signup and view all the answers

    What is the outcome when an acid chloride reacts with an alcohol in the presence of pyridine?

    <p>Synthesis of an ester</p> Signup and view all the answers

    How are unsymmetrical anhydrides named?

    <p>By stating both acids in alphabetical order</p> Signup and view all the answers

    What occurs when a carboxylic acid reacts with PBr3?

    <p>Forms an acid bromide</p> Signup and view all the answers

    What results from the reaction of acid chlorides with ammonia and primary amines?

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

    Which of the following reactions produces a ketone from nitriles?

    <p>Reaction with Grignard reagents</p> Signup and view all the answers

    How are esters typically prepared?

    <p>From carboxylic acids</p> Signup and view all the answers

    Which statement about the reaction of nitriles is true?

    <p>They can yield sp2-hybridized imine anions</p> Signup and view all the answers

    What major product results from the hydrolysis of an ester?

    <p>Alcohol and acid</p> Signup and view all the answers

    Which type of amine reacts with acid chlorides to produce stable products?

    <p>Secondary amines</p> Signup and view all the answers

    What is the result of reducing an amide with LiAlH4?

    <p>Primary amine</p> Signup and view all the answers

    What type of reaction converts a carboxylate with an acid chloride into an acid anhydride?

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

    Which reagent is typically used to reduce esters to primary alcohols?

    <p>LiAlH4</p> Signup and view all the answers

    What is the main product when acid anhydrides react with alcohols?

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

    Study Notes

    Carboxylic Acids and Derivatives

    • Carboxylic acids are a class of organic compounds containing the carboxyl group (-COOH).
    • Carboxylic acids are named by replacing the -e ending of the corresponding alkane name with -oic acid.
    • For example, the carboxylic acid derived from methane is called methanoic acid.
    • Compounds with a carboxyl group bonded to a ring are named using the suffix -carboxylic acid. The carboxyl carbon is not numbered in this system.
    • Common names like formic acid (HCOOH) and acetic acid (CH₃COOH) are also used. Refer to Table 20.1 for specific examples.

    Naming Carboxylic Acids and Nitriles

    • Carboxylic acids (RCO₂H): The carboxyl carbon atom is C1 when naming. Replace the suffix -e of the alkane name with -oic acid.
    • For example, propanoic acid comes from propane, with the carboxyl group on the terminal carbon.

    Nitriles

    • Nitriles(RCN): are closely related to carboxylic acids. When naming, add -nitrile to the alkane name; the nitrile carbon is numbered as C1.
    • Complex nitriles are named as derivatives of corresponding carboxylic acids, replacing the -ic acid end with -onitrile.

    Alternative Names

    • Compounds with a carboxyl group (CO₂H) bonded to a ring use the suffix -carboxylic acid.
    • Formic acid (HCOOH) and acetic acid (CH₃COOH) have common names, see Table 20.1.

    Preparing Carboxylic Acids

    • From Alkenes Oxidative cleavage of an alkene with KMnO₄ can yield a carboxylic acid if the alkene has at least one vinylic hydrogen.
    • From Alcohols Oxidation of a primary alcohol (or aldehyde) with CrO₃ in an aqueous acid can produce a carboxylic acid.

    Carboxylation of Grignard Reagents

    • Grignard reagents react with dry CO₂ to produce a metal carboxylate.
    • This reaction is limited to alkyl halides that can form Grignard reagents.
    • Protonation by addition of aqueous HCl yields the free carboxylic acid.

    Hydrolysis of Nitriles

    • Acid or base catalysis hydrolyzes nitriles, producing a carboxylic acid and ammonia.

    Reactions of Carboxylic Acids

    • Conversion into Acid Chlorides: Using thionyl chloride (SOCl₂).
    • Conversion into Acid Anhydrides: Strong heating of carboxylic acid molecules, removing water.

    Conversion of Carboxylic Acids into Esters

    • Reaction of a carboxylate anion with a primary alkyl halide yields esters. (SN₂ reaction).

    Carboxylic Acid Derivatives

    • An acyl group (RC=O) bonded to a highly electronegative atom (X) or leaving group. Examples include Acid Halides, Acid Anhydrides, Amides, Esters, Thioesters, and Acyl Phosphates.

    General Reaction Pattern

    • Nucleophilic acyl substitution is the primary reaction of carboxylic acid derivatives.

    Naming Carboxylic Acid Derivatives

    • Acid halides (RCOX) are named by replacing the -ic acid (or -carboxylic acid) ending with -yl and the halide name. For example, acetyl (CH₃CO) chloride.

    Naming Acid Anhydrides

    • Symmetrical anhydrides are named by replacing "acid" with "anhydride". Use the related carboxylic acid for naming.
    • Unsymmetrical anhydrides are named citing the two acids alphabetically (e.g., acetic-benzoic anhydride).

    Naming Esters

    • Name R' then carboxyl acid name, replacing "-ic acid" with "-ate".

    Naming Amides

    • Unsubstituted amides replace -ic acid or -oic acid with -amide.
    • Substituted amides include substituent groups (preceded by "N", if applicable).

    Other Reactions and Concepts

    • The relative reactivity of carboxylic acid derivatives plays a critical role in organic reactions, and this is discussed throughout the slides.
    • Substitution reactions, often involving nucleophilic substitutions, are key in preparing different carboxylic acid derivatives.
    • Important reactions for preparation of esters, amides and other carboxylic acid derivatives are discussed.

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    Description

    Explore the fascinating reactions of carboxylic acid derivatives in this quiz. Test your knowledge on Grignard reagents, nitrile hydrolysis, and the conversion of carboxylic acids into acid chlorides. Perfect for advanced organic chemistry learners looking to deepen their understanding of nucleophilic acyl substitution.

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