Complete the mechanism of the given acid-catalyzed imine to enamine tautomerization by adding any missing atoms, bonds, charges, nonbonding electrons, and curved arrows. NH-R is a generic acid with conjugate base :NH,-R in solution. Then, indicate which tautomer predominates at equilibrium.

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Complete the mechanism of the given acid-catalyzed imine to enamine tautomerization by adding any missing atoms,
bonds, charges, nonbonding electrons, and curved arrows. NH-R is a generic acid with conjugate base :NH,-R in
solution. Then, indicate which tautomer predominates at equilibrium.
Step 1: imine: add curved arTows.
Step 2: complete the structure and add
curved arrows.
Select
Draw
Rings Groups More
Erase
Select
Draw
Rings Groups More
Erase
H.
C
H
H,N - R
H,N – R
Transcribed Image Text:Complete the mechanism of the given acid-catalyzed imine to enamine tautomerization by adding any missing atoms, bonds, charges, nonbonding electrons, and curved arrows. NH-R is a generic acid with conjugate base :NH,-R in solution. Then, indicate which tautomer predominates at equilibrium. Step 1: imine: add curved arTows. Step 2: complete the structure and add curved arrows. Select Draw Rings Groups More Erase Select Draw Rings Groups More Erase H. C H H,N - R H,N – R
Step 3: complete the structure and add
Step 4: complete the structure of the enamine.
curved arrows.
Select
Draw
Rings
Groups
More
Erase
Select Draw Rings Groups More
Erase
H
H
H,N
H,N -
H.
H
H
H
2 Q
The predominant species at equilibrium is the
Transcribed Image Text:Step 3: complete the structure and add Step 4: complete the structure of the enamine. curved arrows. Select Draw Rings Groups More Erase Select Draw Rings Groups More Erase H H H,N H,N - H. H H H 2 Q The predominant species at equilibrium is the
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