535 - Practice Problem 5‐35 – Answer Propose a...

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Unformatted text preview: Practice Problem 5‐35 – Answer Propose a mechanism for formation of the bracketed intermediate, and for the bicyclic ketone formed in the following reaction sequence. Practice Problem 5‐36 – Answer How could you prepare the following cyclohexenones by combining a Stork enamine reaction with an intramolecular aldol condensation? (a) (b) (c) Practice Problem 5‐37 – Answer Show how to convert 2‐methylpropylbenzene into 4‐phenyl‐3‐buten‐2‐one. You must use 2‐methylpropylbenzene as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. Retrosynthetic analysis: Synthesis: Practice Problem 5‐39 – Answer Show how to convert ethanol into 2‐pentanone. You must use ethanol as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. Retrosynthetic analysis: Synthesis: Practice Problem 5‐40 – Answer Show how to convert cyclohexane and ethanol into racemic ethyl 2‐oxocyclopentanecarboxylate. You must use ethanol and cyclohexane as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. Retrosynthetic analysis: Synthesis: Practice Problem 5‐41 – Answer Show how to convert ethanol, formaldehyde, and acetone into racemic ethyl 2‐acetyl‐5‐oxohexanoate. You must use ethanol, formaldehyde, and acetone as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. Retrosynthetic analysis: Synthesis: Practice Problem 5‐42 – Answer Show how to convert cyclohexane and ethanol into racemic 2‐acetylcyclohexanone. You must use ethanol and cyclohexane as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. Retrosynthetic analysis: Synthesis: Practice Problem 5‐43 – Answer Show how to convert 2‐oxepane and ethanol into 1‐cyclopentenecarbaldehyde. You must use 2‐oxepane as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. Retrosynthetic analysis: Synthesis: Practice Problem 5‐44 – Answer In each part below, propose a sequence of reactions to prepare the indicated target compound from the indicated starting material. You may also use any other organic and/or inorganic reagents necessary. (a) Synthesis: (b) Synthesis: ...
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This note was uploaded on 10/25/2010 for the course CH 310n taught by Professor Iverson during the Summer '08 term at University of Texas.

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