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Synthetic Cheatsheet quiz

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  • What is the first step required to functionalize an unreactive alkane in organic synthesis?
    The first step is alkane halogenation, typically using a radical reaction like Br2 over heat to add a halogen as a functional group.
  • What type of reaction is used to add a halogen to an alkane?
    A radical reaction, such as using Br2 with heat, is used to halogenate an alkane.
  • What is an organometal, and why is it important in synthesis?
    An organometal is a molecule containing a carbon-metal bond, and it is important because it acts as a strong nucleophile for forming new carbon-carbon bonds.
  • Which two organometals are commonly used for chain extension in organic synthesis?
    Sodium alkynides and Grignard reagents are commonly used organometals for chain extension.
  • What is the main electrophile used with organometals to form new carbon-carbon bonds?
    Alkyl halides are the main electrophiles used with organometals to form new carbon-carbon bonds.
  • How can you move a functional group from one position to another within a molecule?
    By performing alternating elimination and addition reactions, you can move a functional group to a different position in the molecule.
  • What type of elimination moves a group toward a more substituted (central) position, and what base is typically used?
    A Zaitsev elimination moves a group toward a more substituted position, using a small, strong base like NaNH2 or NaH.
  • Which bases are considered bulky and favor Hoffman elimination?
    Bulky bases like LDA, t-Butoxide, and LiTMP favor Hoffman elimination, which moves the group toward a less substituted position.
  • What is the difference between Markovnikov and anti-Markovnikov addition?
    Markovnikov addition adds a group to the more substituted carbon, while anti-Markovnikov addition adds to the less substituted carbon.
  • Which reagents are used for Markovnikov addition of alcohol to a double bond?
    Acid-catalyzed hydration (H2SO4/H2O) and oxymercuration (Hg(OAc)2/H2O, then NaBH4/OH-) are used for Markovnikov addition of alcohol.
  • What reagent is used for Markovnikov addition of a halogen to a double bond?
    HX (hydrogen halide) is used for Markovnikov addition of a halogen to a double bond.
  • Which reaction and reagents are used for anti-Markovnikov addition of alcohol?
    Hydroboration-oxidation (BH3/THF, then H2O2/NaOH) is used for anti-Markovnikov addition of alcohol.
  • How do you achieve anti-Markovnikov addition of a halogen to a double bond?
    By using a radical reaction with HX and peroxides, you achieve anti-Markovnikov addition of a halogen.
  • When starting with a double bond and needing to move a functional group, which reaction type should you perform first?
    You should perform an addition reaction first if you start with a double bond.
  • If you start with an alkyl halide or alcohol and want to move a functional group, what is your first step?
    You should perform an elimination reaction first if you start with an alkyl halide or alcohol.