Ketal formation - 2 NR with the acid’s anion This yields...

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Ketal/acetal formation (only acid-catalyzed will work!): 1. Protonate w/ acid 2. Nu attack on carbocation by ROH 3. Attack H (on ROH) with the acid's anion This yields the hemi-ketal! 4. Protonate the -OH oxygen with acid to make water, a good LG 5. Nu attack on carbocation by ROH 6. Attack H (on ROH) with the acid's anion This yields the ketal! Dithiane formation: 1. Same mech as ketal/acetal formation! Imine formation:  Closely related to mech. for ketal/acetal formation! 1. Protonate w/ acid (HOAc) 2. Nu attack on carbocation by a  primary  amine 3. Attack H (on H 2 NR) with the acid’s anion This yields the carbinal amine! 4. Protonate the –OH oxygen with acid to make water, a good LG 5. Attack H (on HNR) with the acid’s anion This yields the imine! Enamine formation: First 4 steps are (almost) identical to imine formation! 1. Protonate w/ acid 2. Nu attack on carbocation by a  secondary  amine 3. Attack H (on H
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Unformatted text preview: 2 NR) with the acid’s anion This yields the carbinal amine! 4. Protonate the –OH oxygen with acid to make water, a good LG 5. Attack H (part of a C-H adjacent to the C-N bond) with the acid’s anion E1 results in a double bond formation This yields the enamine! Wolff-Kishner rxn: (Aldehyde/Ketone Alkane) 1. HNNH 2 – add’n to the carbonyl carbon; H + add’n to the carbonyl oxygen to make–OH 2. Attack H (on HNNH 2 ) with – OH; push the electrons; C=N double bond forms; -OH leaves 3. A second – OH comes in; attacks H (on NNH 2 ); push the electrons to make the carbanion 4. Carbanion steals an H + from H 2 O to make a neutral molecule 5. A third – OH comes in; attacks H (on NNH); push the electrons to make N N Ξ leave; result is a carbanion 6. Carbanion steals an H + from H 2 O This yields the alkane!...
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Ketal formation - 2 NR with the acid’s anion This yields...

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