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Review of Nitriles quiz

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  • What are the three main methods for synthesizing nitriles?
    The three main methods are SN2 reactions, cyanohydrin formation, and amide dehydration.
  • In an SN2 reaction to form a nitrile, what acts as the nucleophile?
    The cyanide ion (CN-) acts as the nucleophile, displacing the halide from the alkyl halide.
  • What happens to the configuration of the carbon center during an SN2 reaction forming a nitrile?
    The configuration inverts, so if the leaving group was wedged, the incoming cyanide will be dashed, and vice versa.
  • What is formed when a cyanide ion adds to an aldehyde or ketone?
    A cyanohydrin is formed, which has a new chiral center at the former carbonyl carbon.
  • Why is the carbon in a cyanohydrin a chiral center?
    Because after addition, the carbon is attached to four different groups, making it chiral.
  • What reagents are commonly used for amide dehydration to form nitriles?
    Diphosphorus pentoxide (P2O5) or Thionyl Chloride (SOCl2) are commonly used.
  • What is lost from a primary amide during dehydration to form a nitrile?
    Water is lost, specifically the oxygen from the carbonyl and two hydrogens from the nitrogen.
  • What type of bond forms between carbon and nitrogen in a nitrile?
    A triple bond forms between the carbon and nitrogen.
  • What are the main types of reactions that nitriles undergo?
    Nitriles undergo hydrolysis, reduction, and conversion to ketones.
  • What is the product of acidic hydrolysis of a nitrile?
    Acidic hydrolysis produces a carboxylic acid and ammonium ion (NH4+).
  • What is formed when a nitrile undergoes basic hydrolysis?
    A carboxylate anion (or carboxylate salt) and ammonia are formed.
  • Which reagents can reduce nitriles to primary amines?
    Lithium aluminum hydride (LiAlH4) or hydrogen gas (H2) over a metal catalyst like palladium.
  • What happens to the C≡N bond during reduction of a nitrile?
    The triple bond is reduced to a single bond, forming a CH2-NH2 group.
  • How can a nitrile be converted to a ketone?
    By reacting it with a Grignard reagent followed by hydrolysis.
  • What intermediate is formed when a nitrile reacts with a Grignard reagent before hydrolysis?
    A deprotonated imine intermediate is formed, which is then hydrolyzed to a ketone.