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505 - Practice Problem 5‐5 – Answer When a 1:1 mixture...

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Unformatted text preview: Practice Problem 5‐5 – Answer When a 1:1 mixture of acetone and 2‐butanone is treated with base, six aldol products are possible. Draw a structural formula for each product. Practice Problem 5‐6 – Answer Draw a structural formula for the product of each crossed aldol reaction and for the compound formed by dehydration of each aldol product. Practice Problem 5‐7 – Answer Show how to prepare each α,β‐unsaturated aldehyde or ketone by an aldol reaction followed by dehydration of the aldol product. Practice Problem 5‐8 – Answer When treated with base, the following compound undergoes an intramolecular aldol reaction to give a product containing a ring (yield 78%). Propose a structure for this product. Practice Problem 5‐9 – Answer Cyclohexene can be converted to 1‐cyclopentenecarbaldehyde by the following series of reactions. Propose a structure for each intermediate compound. Practice Problem 5‐10 – Answer How might you bring about the following conversion? Practice Problem 5‐11 – Answer How might you synthesize each of the following compounds using an aldol reaction? In each case, show the structure of the starting aldehyde(s) or ketone(s) you would use. (a) C6H5CH=CHCOC6H5 (b) (c) 2‐Cyclohexenone (d) Practice Problem 5‐12 – Answer Propose a mechanism for this acid‐catalyzed aldol reaction and the dehydration of the resulting aldol product. Mechanism: [Note: TsOH, a common sulfonic acid (ArSO3H), is used as the acid catalyst in this mechanism] ...
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