Chemistry 3719 Chapter 10
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Which molecule is more stable, 1,3-pentadiene or 1,4-pentadiene? Why?
1,3-pentadiene since the double bonds are conjugated
Why is an allylic radical more stable than a 1-propyl radical?
The double bond in the allyl radical helps stabilize through resonance
What conditions are required to convert propene to 3-bromopropene?
Br2 and either light or heat (radical bromination)
Why do 1,3-dienes need to be s-cis oriented for the Diels-Alder reaction to be successful?
The diene must present its frontier orbitals in the same direction so that they may overlap with the pi bond of the dienophile
Why is s-cis to s-trans interconversion hindered in acyclic 1,3-dienes?
There is significant overlap between the C-2 and C-3 p orbitals so the C-2-C-3 bond has some pi character.
Why do SN1 reactions of allylic halides occur faster than in simple alkyl systems?
The allyl carbocation is stabilized by resonance and is formed faster than a simple alkyl carbocation
Which is typically more stable in a chemical reaction, the kinetic or thermodynamic product?
The thermodynamic product
Is the Diels-Alder reaction typically a stepwise or a concerted process?
Concerted; all bonds form and break at the same time
Which dienes are usually more stable, isolated or conjugated, and why?
Conjugated; extra overlap between the pi bonds
Are the s-cis and s-trans forms of an acyclic 1,3-diene isomers or conformers?
Conformers; they are readily interconverted unlike isomers
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