Chapter 6: Problem 8
Complete these reactions.
(a)
Chapter 6: Problem 8
Complete these reactions.
(a)
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Get started for freeState the number and kind of stereoisomers formed when
\((R)-3\)-methyl-1-pentene is treated with these reagents. Assume that the
starting alkene is enantiomerically pure and optically active. Will each
product be optically active or inactive?
As we have seen in this chapter, carbon-carbon double bonds are electron-rich regions that are attacked by electrophiles (e.g., HBr); they are not attacked by nucleophiles (e.g., diethylamine). (a racemic mixture) \(\mathrm{Et}_{2} \mathrm{NH}+\longrightarrow\) No reaction Diethylamine (a nucleophile) However, when the carbon-carbon double bond has a carbonyl group adjacent to it, the double bond reacts readily with nucleophiles by nucleophilic addition (Section 19.8). Diethylamine (a nucleophile) Account for the fact that nucleophiles add to a carbon-carbon double bond adjacent to a carbonyl group and account for the regiochemistry of the reaction.
reating cyclohexene with \(\mathrm{HBr}\) in the presence of acetic acid gives
bromocyclohexane \((85 \%)\) and cyclohexyl acetate \((15 \%)\).
Using the table of average bond dissociation enthalpies at $25^{\circ} \mathrm{C}$, determine which of the following reactions are energetically favorable at room temperature. Assume that \(\Delta S=0\).
Reaction of \(\alpha\)-pinene with borane followed by treatment of the resulting trialkylborane with alkaline hydrogen peroxide gives the following alcohol. \(\alpha\)-Pinene Of the four possible cis, trans isomers, one is formed in over \(85 \%\) yield. (a) Draw structural formulas for the four possible cis, trans isomers of the bicyclic alcohol. (b) Which is the structure of the isomer formed in \(85 \%\) yield? How do you account for its formation? Create a model to help you make this prediction.
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