Chapter 20: Q18P a. (page 1065)
Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.
(a)
(b)
(c)
Short Answer
(a)
(b)
(c)
Chapter 20: Q18P a. (page 1065)
Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.
(a)
(b)
(c)
(a)
(b)
(c)
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b)
The 2000 Nobel Prize in Chemistry was awarded for work on polyacetylenes. Acetylene can be polymerized using a Ziegler-Natta catalyst. The cis or trans stereochemistry of the products can be controlled by careful selection and preparation of the catalyst. The resulting polyacetylene is an electrical semiconductor with a metallic appearance. cis-Polyacetylene has a copper color, and trans-polyacetylene is silver.
(a) Draw the structures of cis- and trans-polyacetylene.
(b) Use your structures to show why these polymers conduct electricity.
(c) It is possible to prepare polyacetylene films whose electrical conductivity is anisotropic. That is, the conductivity is higher in some directions than in others. Explain how this unusual behavior is possible.
Show how you would synthesize any of the standard amino acids from each starting material. You may use any necessary reagents.
Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(a) isopentyl alcohol isopentyl acetate (banana oil)
(b) 3-ethylpentanoic acid3-ethylpentanenitrile
(c) isobutylamineN-isobutylformamide
(d) ethyl acetate3-methylpentan-3-ol
(e) cyclohexylamineN-cyclohexylacetamide
(f) bromocyclohexanedicyclohexylmethano
(g)
(h)
(a) Propose a mechanism for the following reaction:
(b) Use the bond-dissociation enthalpies given in Table 4-2 (page 203) to calculate the value of ∆H° for each step shown in your mechanism. (The BDE for is about 280 kJ/mol, or 67 kcal/mol.) Calculate the overall value of ∆H° for the reaction. Are these values consistent with a rapid free-radical chain reaction?
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