Chem 334 1st Edition Lecture 23Outline of Last Lecture I. AminesOutline of Current Lecture II. Acidity of AminesIII. Making aminesCurrent LectureAcidity of amines:1. Aromatic amines are more acidic than aliphatic amines because the free lone pair of the deprotonated compound is involved in resonance.2. Aromatic amines with an electron withdrawing group attached to them are more acidic than aromatic amines with no other substituents, due to the partial positive charge. However, aromatic amines with no substituents attached to them are more acidic than an aromatic amine with an electron donating group attached to it, due to the fact that there is already high electrondensity in the ring, it doesn’t need more.3. For aromatic amines with electron withdrawing groups attached, having the electron withdrawing group in the ortho/para position is more acidic than having the electron withdrawing group in the meta position.4. For aromatic amines with electron donating groups attached, having the electron donating groupin the ortho/para position is less acidic than having the electron withdrawing group in the meta position. This is because both the electron donating group and the amine are putting electron density on the same carbon when in the para position, which is more destabilizing than when they are in the meta position.Overall, amine acidity goes like this (from most acidic to least acidic); NH3NH3NH3NH3NH3>>>> EWG EWG EDG EDGThese notes represent a detailed interpretation of the professor’s lecture. GradeBuddy is best used as a supplement to your own notes, not as a substitute.Making amines:1. Reductive Amination: works with aldehydes or ketones, primary or secondary amines O 1. H2N-R N–R H 2. NaBH42. Amide Reduction O LiAlH4 N3. Nitrile Reduction N LiAlH4 NH24. Nitro reductionHNO3, H2SO4 NO2 H2, Pd NH25. Azide ReductionR–N≡N≡N LiAlH4 R–NH2 +
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