Aldehydes and Ketones

0.0(0)
studied byStudied by 0 people
GameKnowt Play
learnLearn
examPractice Test
spaced repetitionSpaced Repetition
heart puzzleMatch
flashcardsFlashcards
Card Sorting

1/7

encourage image

There's no tags or description

Looks like no tags are added yet.

Study Analytics
Name
Mastery
Learn
Test
Matching
Spaced

No study sessions yet.

8 Terms

1
New cards

Nucleophilic Addition

  • Nucleophile initiates the reaction and the aldeyhde/ketone add together during the reaction

2
New cards

Using NaBH4

  • Provides hydride ion as a nucleophile (:H-)

  • Causes reduction of the aldehyde/ketone into an alcohol

3
New cards

Using HCN

  • HCN formed via NaCN in acid

  • Provides :CN- as a nucleophile

4
New cards

Mechanism for NaBH4

  • First is hydride ion

  • Second is hydrogen from the solvent

<ul><li><p>First is hydride ion</p></li><li><p>Second is hydrogen from the solvent</p></li></ul><p></p>
5
New cards

Forming racemate

  • In aldehydes and ketones the atoms are planar

  • Nucleophile has an equal probability of attacking from either side

  • From above, leads to the enantiomer and from below leads to the other enantiomer

  • Forms a racemic mixture

6
New cards

Using HCN

  • Forms hydroxynitriles

  • Image does not show lone pair on oxygen (this needs to be in mechanism!!!)

<ul><li><p>Forms hydroxynitriles</p></li><li><p>Image does not show lone pair on oxygen (this needs to be in mechanism!!!) </p></li></ul><p></p>
7
New cards

Problems with HCN

HCN used to form hydroxynitriles is toxic and so is generated in situ (in the reaction flask) using aqueous acid and an excess of NaCN or KCN

8
New cards

Why are Hydroxynitriles important

  • Important intermediate molecules

  • Can be reacted further through acid catalysed hydrolysis or catalytic reduction

  • Acid catalysed hydrolysis converts -CN nitrile into -COOH carboyxlic acid

  • Catalytic reduction converts -CN nitrile into -CH2NH2 amine