Lecture 7: Aromatic Aldehydes & Ketones
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Questions and Answers

Which type of alcohol is oxidized to form an aldehyde?

  • Tertiary alcohol
  • Primary alcohol (correct)
  • Quaternary alcohol
  • Secondary alcohol

    • What is a common reaction characteristic of aldehydes and ketones?

  • Substitution reaction
  • Nucleophilic addition reaction (correct)
  • Elimination reaction
  • Free radical reaction

    • What is the role of a nucleophile in a nucleophilic addition reaction?

  • It acts as an electron-rich species attacking the electrophilic carbon (correct)
  • It removes a hydroxyl group from the substrate
  • It donates a proton to the reaction
  • It forms an unstable compound that decomposes

    • Which compound will Grignard reagents react with to form a primary alcohol?

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

    What is formed after the protonation of the alkoxide intermediate in a nucleophilic addition reaction?

    <p>An alcohol derivative</p> Signup and view all the answers

    Which of the following types of reactions involve the addition of Hydrogen Cyanide (HCN)?

    <p>Nucleophilic addition reaction</p> Signup and view all the answers

    What happens to the p bond with oxygen during a nucleophilic addition reaction?

    <p>It is broken</p> Signup and view all the answers

    In the context of nucleophilic addition reactions, what is formed as a result of a Grignard reagent reacting with a ketone?

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

    Which of the following correctly describes the naming convention for aliphatic aldehydes in the IUPAC system?

    <p>Replace the final -e of the alkane with -al.</p> Signup and view all the answers

    What structural feature distinguishes ketones from aldehydes?

    <p>Presence of two alkyl groups attached to the carbonyl carbon.</p> Signup and view all the answers

    In what way can aromatic aldehydes be specifically named using IUPAC nomenclature?

    <p>By maintaining the alkane name and adding -carbaldehyde.</p> Signup and view all the answers

    Which statement is correct regarding the functional group of carbonyl compounds?

    <p>They include Aldehydes, Ketones, Carboxylic acids, Esters, and Amides.</p> Signup and view all the answers

    Which of the following names correctly represents a ketone according to IUPAC nomenclature?

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

    What is the correct position designation for a carbonyl carbon in a ketone?

    <p>It should have the lowest possible number when naming.</p> Signup and view all the answers

    What is the peculiar naming method used for some aldehydes that are part of a ring system?

    <p>They are named by adding -carbaldehyde after the ring name.</p> Signup and view all the answers

    Which of the following compounds is NOT classified as a carbonyl compound?

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

    Which statement correctly describes the conversion of 2-pentanone to 2-pentanol?

    <p>It requires a reducing agent.</p> Signup and view all the answers

    In the Knoevenagel condensation, what is the primary type of compound that reacts with the carbonyl compound?

    <p>Carbanion derived from an active methylene compound</p> Signup and view all the answers

    What is the role of phosphorus ylide in the Wittig reaction?

    <p>It reacts with aldehydes to form oxaphosphetanes.</p> Signup and view all the answers

    What is a key difference in the oxidation behavior of aldehydes compared to ketones?

    <p>Aldehydes oxidize easily to acids, while ketones are resistant.</p> Signup and view all the answers

    In a haloform reaction, which structural feature must a ketone or aldehyde possess?

    <p>Presence of a methyl group adjacent to the carbonyl</p> Signup and view all the answers

    What is the byproduct in the haloform reaction when a methyl ketone is treated with iodine?

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

    Which reaction type does a ketone typically undergo when subjected to the appropriate reducing agent?

    <p>Reduction to alcohol</p> Signup and view all the answers

    In the context of the reactions discussed, which reaction specifically involves an active methylene compound?

    <p>Knoevenagel condensation</p> Signup and view all the answers

    Study Notes

    Lecture 7: Aromatic Aldehydes & Ketones

    • Aromatic aldehydes and ketones are a category of carbonyl compounds
    • These compounds contain a carbonyl group (C=O)
    • Examples of carbonyl compounds include aldehydes, ketones, carboxylic acids, esters, and amides
    • Aliphatic aldehydes are named by replacing the "-e" of the corresponding alkane name with "-al"
    • Aldehyde groups attached to ring systems are named by adding "-carbaldehyde" to the ring name
    • Aliphatic ketones are named by replacing the "-e" of the corresponding alkane name with "-one"
    • The carbon atom of the carbonyl group is numbered to give it the lowest possible number
    • Ketones can also be named by naming the two groups attached to the carbonyl carbon and adding the word "ketone"

    Intended Learning Outcomes (ILO's)

    • Students will be able to identify structural differences between aldehydes and ketones
    • Students will be able to name aldehydes and ketones using IUPAC nomenclature
    • Students will be able to synthesize aldehydes and ketones
    • Students will be able to explain nucleophilic reactions at the carbonyl carbon

    Aromatic Aldehyde and Ketones - Page 15

    • Aromatic aldehydes and ketones are a class of carbonyl compounds
    • The carbonyl group (C=O) is a characteristic feature of these compounds

    Nomenclature of Aldehydes and Ketones - Page 15

    • Aliphatic aldehydes are named by replacing the final "-e" in the alkane name with "-al"
    • Aldehydes attached to a ring system are named by adding "-carbaldehyde" to the ring name
    • Aliphatic ketones are named by replacing the "-e" in the alkane name with "-one"
    • The carbonyl carbon is numbered to provide the lowest possible number

    Synthesis of Aldehydes and Ketones from Alcohols

    • Primary alcohols can be oxidized to aldehydes
    • Secondary alcohols can be oxidized to ketones

    Reactions of Aldehydes and Ketones - Page 221

    • The most important reaction of aldehydes and ketones are nucleophilic addition reactions
    • A nucleophile (electron-rich species) reacts with the electron-deficient carbonyl carbon
    • Nucleophilic addition involves three fundamental events:
      • Formation of a new C-Nu bond
      • Breaking of the C=O bond
      • Protonation of the alkoxide intermediate
    • Nucleophilic addition is a key reaction for aldehydes and ketones

    Example of Nucleophilic Addition Reaction (Addition of Hydrogen Cyanide (HCN)) - Page 238

    • Great care must be taken when working with HCN due to its toxicity and volatility
    • Reactions involving HCN should be conducted in a fume hood

    Addition of Organometallic Compounds: Grignard Reagents (RMgX) - Page 240

    • Grignard reagents react with formaldehyde to produce primary alcohols
    • Grignard reagents react with other aldehydes to yield secondary alcohols
    • Grignard reagents react with ketones to generate tertiary alcohols

    Addition of Derivatives of Ammonia

    • Aldehydes and ketones react with ammonia derivatives to form different compounds

    Addition of Alcohols (Page 224)

    • Aldehydes and ketones react with alcohols to form hemiacetals and acetals

    Addition of Hydride Ion

    • Reducing agents like NaBH4 convert ketones into alcohols

    Addition of Carbanions: The Knoevenagel Condensation - Page 372

    • The Knoevenagel reaction is a modified aldol reaction
    • It involves the reaction of carbonyl compounds with active methylene compounds in the presence of weakly basic conditions
    • It proceeds through an enolate intermediate

    Addition of Ylides: The Wittig Reaction

    • The Wittig reaction involves the reaction of aldehydes or ketones with phosphorous ylides
    • This results in the formation of alkenes.

    Oxidation Reactions

    • Aldehydes are easily oxidized to carboxylic acids
    • Ketones are more resistant to oxidation because they lack a readily oxidizable hydrogen atom

    Haloform Reaction

    • This reaction occurs with methyl ketones
    • The methyl ketone is converted to a carboxylate ion, X, and a haloform (e.g., chloroform)
    • This reaction is generally accompanied by the formation of a yellow precipitate (iodoform)

    References, Textbooks, and Online Resources

    • Several textbooks (Elements of organic chemistry by H. Zimmerman and I. Zimmerman, Solomons, T.W. Graham Organic Chemistry) and online references (chem.libretexts.org and khanacademy.org) are cited.

    Class Activity-1

    • Students are instructed to provide structural formulas for cyclohexanecarbaldehyde, 3-methylcyclohexanecarbaldehyde, and 2,2-dibromocyclopentanecarbaldehyde

    Natural Compounds Containing Aldehyde and Ketones

    • Examples of natural compounds that contain aldehydes and ketones, including cinnamaldehyde, vanillin, citral, and various hormones (testosterone, progesterone, cortisone) are highlighted in structural formulas and their source.

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    Description

    Dive into the world of aromatic aldehydes and ketones in this quiz. Understand the structural differences and naming conventions according to IUPAC nomenclature. Test your knowledge on identifying carbonyl compounds and their properties.

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