The reaction between an aldehyde and an amine results in the formation of a functional

Chapter 2, Problem 2.74

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The reaction between an aldehyde and an amine results in the formation of a functional group called an imine, as shown in the following general reaction: + O R R NH2 N R R An imine Consider the reactants AD, which have been used in the synthesis of novel self-assembling molecules with unique and dynamic architectures (Langmuir 2012, 28, 1456714572). ! ! ! ! A D O O O H N (CH2)10 (CH2)10 (CH2)10 (CH2)10 N O O N N H O H2N NH2 C B H2N NH2 (a) Draw the product of the reaction between: i. A and C (2:1 molar ratio) ii. C and D (1:2 molar ratio) iii. A and B (2:1 molar ratio) iv. B and D (1:2 molar ratio) (b) What is the relationship between the products of reactions iii and iv?

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