Nucleophilic Addition to the Carbonyl group

• what are the only carbonyl groups considered?

  aldehydes and ketones
• what are the two mechanism steps:

  • nucleophilic addition to the carbonyl group
  • protonation of the anion
• where would a nucleophilic (electron rich) attack take place?

  on electron-poor areas
• why does electron rich attack electron poor?

  electrostatic interaction
• what are the mildest reagent to reduce aldehyde and ketones to alcohols?

  borohydrides
• what has a similar reaction mechanism to borohydrides?

  Lithium aluminum hydrides
• what is a grinard reagent?

  organomagnesium
• what would happen if you mixed an organometalic with water?

  they are destroyed by protonation
• how to prepare a organometallic?

  alkyl, vinyl and aryl halides
• how are organometallics made from organometallic reagent from alkynes?

  by deprotonation
• Describe sodium amide:

  • strong base
  • made by dissolving sodium metal in liquid ammonia
• What are some neutral nucleophiles?

  water, alcohol and amines
• when do hemiacetals and acetals form?

  alcohol react with aldehydes and ketones
• when doe hydrated from?

  water reacts with aldehydes and ketones
• when do imine form?

  when amines react with aldehydes and ketones
• imine

  
• Hemiacetal

  
• acetal

  
• why is an aldehyde more likely to be hydrated than a ketone?

  Steric factors
• what are more reactive aldehydes or ketones?

  Aldehydes
• what is a strained ketone?

  small ring ketone (3/4 membered)
• Are strained ketones reactivity?

  Very reactive towards nucleophilic attack
• What is the inductive effect?

  electronegative elements (withdraw electron density towards it away bonds in the vicinity)
• what does an increasing K value mean?


  increases inductive effect but decreases steric effects
• How do acid catalyst work?


  making the carbonyl group more electrophilic
• How does base catalyst work?

  Making the nucleophile more nucleophilic
• What type of catalysis can form a hemiacetal?

  acid or base
• what time of catalysis can form acetal?

  Acid catalysis
• How you form an imine from a aldehyde/ketone?

  under acid catalysis
• what is more stable hemiaminal or hemiacetal?

  hemiacetal
• iminium ion

  
• How to produce an amine from a carbonyl?

  Reduction
• what is the reducing agent of a aldehyde to amine?

  Sodium cyanoborohydride (milder version of sodium borohydride)
• ketone not reduced by sodium cyanoborohydride

  to alcohol