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Overview of Nucleophilic Addition of Solvents quiz

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  • What is the key feature that makes carbonyl carbons highly reactive in nucleophilic addition reactions?
    The carbonyl carbon has a strong partial positive charge, making it highly susceptible to attack by nucleophiles and even neutral solvents.
  • Why do carbonyl reactions with neutral solvents typically require a catalyst?
    These reactions need acid or base catalysts because neutral solvents are not strong nucleophiles, so catalysis helps facilitate the reaction.
  • What is the first step in an acid-catalyzed nucleophilic addition mechanism to a carbonyl?
    The first step is protonation of the carbonyl oxygen to increase its electrophilicity.
  • What product forms when water reacts with a carbonyl compound in the presence of acid?
    The product is a hydrate, specifically a geminal diol (gem diol).
  • How does the number of alcohol equivalents affect the products formed with carbonyls?
    One equivalent of alcohol forms a hemiacetal, while two equivalents form an acetal.
  • What distinguishes a hemiacetal from an acetal structurally?
    A hemiacetal has one OH and one OR group attached to the central carbon, while an acetal has two OR groups.
  • What reagent is used to form thioacetals from carbonyl compounds?
    Thioacetals are formed using two equivalents of a thiol (RSH) and BF3 as the acid catalyst.
  • What is the difference between acetals and thioacetals?
    Acetals have two OR groups, while thioacetals have two SH groups attached to the central carbon.
  • What product forms when a primary amine reacts with a carbonyl compound?
    A primary amine reacts to form an imine, which has a double bond between carbon and nitrogen.
  • What is the product when a secondary amine reacts with a carbonyl compound?
    A secondary amine forms an enamine, which features a double bond adjacent to the nitrogen atom.
  • Why are hemiacetals generally unstable, and when are they stable?
    Hemiacetals are generally unstable unless they are cyclic, in which case they can be stable.
  • What is a common use for acetals in organic synthesis?
    Acetals are used as protecting groups for carbonyl compounds.
  • How can thioacetals be converted to alkanes?
    Thioacetals can be reduced to alkanes using Raney nickel as a reducing agent.
  • What is the Wolf-Kishner reduction, and what does it accomplish?
    The Wolf-Kishner reduction uses a hydrazone derivative, strong base, and heat to convert a carbonyl into an alkane.
  • What type of reaction do enamines undergo with alkyl halides, and what is the result?
    Enamines react with alkyl halides via SN2 to form alpha-substituted carbonyl compounds.