PMT flashcards Carbon-carbon bond formation

• What type of mechanism is involved in the reaction between haloalkanes and cyanide ions?

  Nucleophilic substitution

  
• What is the mechanism of the reaction between 2-bromopropane and cyanide ions?

  It involves nucleophilic substitution

  
• What type of reaction occurs between carbonyl compounds and cyanide ions?

  Nucleophilic addition
• What is the mechanism for the reaction of ethanal and cyanide?

  It involves nucleophilic addition
• What is the equation for the reduction to butanenitrile?

  [H] = H2/Ni
• How can you form a carboxylic acid from a nitrile?

  Through acid hydrolysis
• What type of catalyst is used for a Friedel-Crafts reaction?

  A halogen carrier (e.g. AlCl3)
• What is the equation to form an electrophile for acylating benzene using AlCl3 and RCOCl?

  AlCl3 + RCOCl → AlCl4- + RCO+
• How can you use a Friedel-Crafts mechanism to add a methyl group to a benzene ring?

  Use a halogenoalkane and AlCl3
• What is the mechanism for the alkylation of benzene?

  It involves a Friedel-Crafts mechanism

  
• What are the steps in the nucleophilic substitution mechanism for haloalkanes and cyanide ions?

  1. Nucleophile attacks the carbon atom
  2. Leaving group departs
  3. Product formation
• What are the steps in the nucleophilic addition mechanism for carbonyl compounds and cyanide ions?

  1. Nucleophile attacks the carbonyl carbon
  2. Formation of a tetrahedral intermediate
  3. Protonation to form the final product
• What is the process of acid hydrolysis of nitriles to form carboxylic acids?

  1. Nitrile reacts with water
  2. Acid catalyst is used
  3. Carboxylic acid is formed
• What is the Friedel-Crafts mechanism for adding groups to benzene rings?

  1. Formation of an electrophile
  2. Electrophile attacks the benzene ring
  3. Rearrangement and product formation