Orgo Review - Day 2 - Part 1

What is the IUPAC name of the molecule shown?

• (1R)-1-bromocyclohex-3-ene

• (1S)-1-bromocyclohex-3-ene

• (4R)-4-bromocyclohex-1-ene

• (4S)-4-bromocyclohex-1-ene

What is the most stable conformer of pentane looking down the C2-C3 bond?

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What is the major product of the reaction shown?

• (1R)-1-chloro-1-methylcyclohexane

• (1S)-1-chloro-1-methylcyclohexane

• 1-chloro-1-methylcyclohexane

• 3-chloromethylcyclohexane

Which compound would undergo an S_N1 solvolysis reaction most rapidly with water?

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What is the major product of this reaction sequence?

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How many signals do you expect to see in the proton decoupled ¹³C NMR spectrum of this molecule?

• 5 signals

• 6 signals

• 7 signals

• 8 signals

What resonance structure is the major contributor? (i.e. which is most significant?)

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How many lone pairs of electrons are delocalized in this molecule?

• zero

• one

• two

• three