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Chapter 20: 51E (page 678)

1,6 Hexanediamine, a starting material needed for making nylon, can be made from 1,3 butadiene. How would you accomplish the synthesis?

H2C=CHCH=CH2鈫�?H2NCH2CH2CH2CH2CH2CH2CH2NH2

Short Answer

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1,6-Hexanediamine can be synthesized from 1,3-butadiene through the steps

Step by step solution

01

Definition of synthesis

The construction of complex chemical compounds from simpler ones is defined as synthesis.

02

Explanations

1,3 butadiene is a conjugated diene. Hence it is treated with bromine, and a 1,4-addition of bromine to the diene takes place to yield 1,4-dibromobut-2-ene. Treatment with NaCN converts the dibromide to 1,4-dicyanobut-2-ene. When treated with LiAlH4 the nitrile groups are reduced to -CH2NH2 groups to give 1,6-dicyanohex-3-ene. The double bond is not reduced by LiAlH4. It is reduced by treating with H2,Pd/C to get 1,6-hexane diamine.

1,6-Hexanediamine can be synthesized from 1,3-butadiene through the steps

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Most popular questions from this chapter

Which method 鈥� Grignard carboxylation or nitrile hydrolysis would you use for each of the following reactions? Explain.

How would you carry out the following transformations? More than one step is needed in each case.

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(a) Lactic acid, Ka = 8.4 脳 10-4

(b) Acrylic acid, Ka = 5.6 脳 10-6

Thioglycolic acid, HSCH2CO2H, a substance used in depilatory agents
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  1. LiAlH4,鈥�then鈥�H3O+
  2. N-Bromosuccinimide in CCl4
  3. CH3MgBr鈥�in鈥�ether,鈥�then鈥�H3O+
  4. KMnO4,鈥�H3O+
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