Halogenalkanes

• What prefix is used for fluorine in halogenoalkanes?

  Fluoro
• What prefix is used for chlorine in halogenoalkanes?

  Chloro
• What prefix is used for bromine in halogenoalkanes?

  Bromo
• What prefix is used for iodine in halogenoalkanes?

  Iodo
• How are halogenoalkanes named?

  Based on original alkane with halogen prefix
• What is the name of the compound with the formula C3H7Br?

  1-bromopropane
• How are substituents listed in halogenoalkanes?

  Alphabetically
• What defines a primary halogenoalkane?

  One carbon attached to the carbon with halogen
• What defines a secondary halogenoalkane?

  Two carbons attached to the carbon with halogen
• What defines a tertiary halogenoalkane?

  Three carbons attached to the carbon with halogen
• What are the types of reactions halogenoalkanes undergo?

  • Nucleophilic substitution reactions
  • Elimination reactions
• What is a nucleophile?

  Electron pair donator
• What happens in a substitution reaction of halogenoalkanes?

  Swapping a halogen for another atom or group
• What does the rate of substitution reactions depend on?

  The strength of the C-X bond
• Which halogenoalkane is the fastest to substitute?

  Iodoalkanes
• Which halogenoalkane is the slowest to substitute?

  Fluoroalkanes
• What is the mechanism of nucleophilic substitution reactions?

  • Nucleophile attacks the positive carbon
  • Curly arrows show electron movement
  • Starts from a lone pair or bond center
• What is the result of hydrolysis of a halogenoalkane?

  Splitting by reaction with water
• What is the role of aqueous silver nitrate in hydrolysis reactions?

  Forms silver halide precipitate
• What does the formation of a precipitate indicate in hydrolysis?

  Halide ion has left the halogenoalkane
• What is the precipitate formed with iodoalkanes?

  Yellow precipitate (AgI)
• What is the precipitate formed with bromoalkanes?

  Cream precipitate (AgBr)
• What is the precipitate formed with chloroalkanes?

  White precipitate (AgCl)
• What is the change in functional group when halogenoalkanes react with aqueous hydroxide ions?

  Halogenoalkane to alcohol
• What are the conditions for nucleophilic substitution with hydroxide ions?

  Aqueous solution and warm
• What happens if the solvent is changed to ethanol in nucleophilic substitution?

  An elimination reaction occurs
• How do tertiary halogenoalkanes undergo nucleophilic substitution differently?

  Form a carbocation intermediate first
• Why do tertiary carbocations stabilize the reaction?

  Electron releasing methyl groups surround it
• What is the change in functional group when halogenoalkanes react with cyanide ions?

  Halogenoalkane to nitrile
• What are the conditions for nucleophilic substitution with cyanide ions?

  Heating under reflux
• What is the change in functional group when halogenoalkanes react with ammonia?

  Halogenoalkane to amine
• What are the conditions for nucleophilic substitution with ammonia?

  Heating under pressure in ethanol
• What is the name of the amine formed from 1-bromopropane?

  Propylamine
• What is the IUPAC name for propylamine?

  Propan-1-amine
• What is the naming convention for nitriles?

  Must be at the end of a chain
• What is the name of the nitrile with the formula CH3CH2CN?

  Propanenitrile
• What is the name of the nitrile with the formula CH3C(CH3)CH2CN?

  3-methylbutanenitrile
• What is the process of elimination in halogenoalkanes?


  • Removal of a small molecule (often water)
  • Converts halogenoalkane to alkene
  • Requires alcoholic hydroxide ions
• What are the conditions for elimination reactions with hydroxide ions?

  In ethanol and heat
• What is the effect of solvent on the type of reaction?

  Aqueous leads to substitution, alcoholic to elimination