Base Equilibrium

IMINES Wize Organic Chemistry Lecture Series, 2017 Presented by: Spencer

IMINES

T E ACH I NG OB J E CT I VES

1. General Synthesis/Hydrolysis of Imines 2. Mechanism: Imine Formation 3. Mechanism: Imine Hydrolysis

4. Reductive Amination 5. Review Questions

IMINES

SY NT H E SI S

Note: The above hemiaminals cannot be isolated experimentally

IMINES

SY NT H E SI S

Circle the Imine functionality in each compound. Propose amine and carbonyl starting materials for each imine.

Note: The structure of the acid catalyst is not important as long as it is a strong acid!

IMINES

H Y DROLYSI S

Predict the products

IMINES

ME CH ANI SM OF FOR MATI ON

IMINES

ME CH ANI SM OF H Y DROLYSI S

IMINES

R E DUCT IV E AMI NATI ON

IMINES

R E DUCT IV E AMI NATI ON

Provide the reagents(s) necessary for the following transformation

IMINES

R E DUCT IV E AMI NATI ON

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IMINES

R E V I E W QUE ST I ONS Fill in the blanks:

IMINES

R E V I E W QUE ST I ONS

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IMINES

R E V I E W QUE ST I ONS

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IMINES

R E V I E W QUE ST I ONS The following graph shows the pH dependence of the reaction rate in generic imine synthesis reactions. Using pictures, justify the reduction of rate at higher and lower pHs. (Hint: draw the mechanism for an imine reaction).