Chapter 14: Problem 6
Show how the following compound could be prepared from any compound containing ten carbons or fewer.
Chapter 14: Problem 6
Show how the following compound could be prepared from any compound containing ten carbons or fewer.
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Get started for freeShow how to prepare each compound from the given starting compound through the use of a lithium diorganocopper (Gilman) reagent. (a) 4-Methylcyclopentene from 4 -bromocyclopentene (b) ( \(Z)\)-2-Undecene from \((Z)\)-1-bromopropene (c) 1-Butylcyclohexene from 1-iodocyclohexene (d) 1-Decene from 1-iodooctane (e) 1,8 -Nonadiene from 1,5 -dibromopentane
Using your old and new roadmaps as a guide, show how to convert 1 -bromo- 3 -methylbutane into 2,7-dimethyloctane. You must use 1-bromo-3-methylbutane as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.
Show how to convert 1-bromopentane to each of these compounds using a lithium diorganocopper (Gilman) reagent. Write an equation, showing structural formulas, for each synthesis. (a) Nonane (b) 3 -Methyloctane (c) 2,2 -Dimethylheptane (d) 1-Heptene (e) 1-Octene
One of the most important uses for Grignard reagents is their addition to carbonyl compounds to give new carbon-carbon bonds (Section 16.5). In this reaction, the carbon of the organometallic compound acts as a nucleophile to add to the positive carbon of the carbonyl. (a) Give a mechanism for the first step of the reaction. (b) Explain the function of the acid in the second step.
Using your old and new roadmaps as a guide, show how 1 -bromobutane can be converted into either of the two products shown by a suitable choice of reagents. Give reagents and conditions for each reaction.
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