Question 1

Devise a multistep synthesis for the following transformation.You may use any organic or inorganic reagents of your choice.Show the reagents necessary for each step and the product of each step.

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Question 2

Is the compound shown here aromatic? Assume planarity.

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Question 3

Draw ortho-methoxytoluene.

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Question 4

Devise a multistep synthesis for the following transformation.You may use any organic or inorganic reagents of your choice.Show the reagents necessary for each step and the product of each step.

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Question 5

What is the product of the following reaction?

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Question 6

Draw the product of the following reaction.

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Question 7

Draw meta-xylene.

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Question 8

Draw a mechanism for the following transformation.Include all lone pairs of electrons, curved arrows, and formal charges.

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Question 9

Which of these two molecules is more reactive in an S_N1 reaction, and why?

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Question 10

Draw the product of the following reaction.

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Question 11

Draw the structure of styrene.

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Question 12

Devise a multistep synthesis for the following transformation.You may use any organic or inorganic reagents of your choice.Show the reagents necessary for each step and the product of each step.

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Question 13

Three alkylbenzene isomers of C₁₀H₁₄ undergo various reactions. Compound A reacts with KMnO₄to give a para substituted benzoic acid. Compound B does not react with KMnO₄. Compound C reacts with KMnO₄ to give benzoic acid. Propose structures for compounds A, B , and C .

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Question 14

Draw a Frost circle for pyrrole.Include and label all bonding molecular orbitals and antibonding molecular orbitals.Indicate the nonbonding energy level.Put the correct number of electrons in
the appropriate orbitals in your drawing.

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Question 15

Which nitrogen in imidazole is more basic? Explain your answer.

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Question 16

In furan, what type of orbital do each of the two lone pairs on oxygen occupy?

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Question 17

Draw the structure of toluene.

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Question 18

The compound below is called benzofuran. Suggest an isomeric structure containing fused 5 -membered heterocycle. Does it obey the 4n +2 rule?

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Question 19

Which of these two molecules is more reactive in an S_N2 reaction, and why?

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Question 20

Draw the structures of the following compounds and place them in the order of increasing boiling points: toluene, p-ethyltoluene, p-ethylbenzoic acid, p-diethylbenzene.

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Quiz 14: Aromaticity

Devise a multistep synthesis for the following transformation.You may use any organic or inorganic reagents of your choice.Show the reagents necessary for each step and the product of each step.

Is the compound shown here aromatic? Assume planarity.

Draw ortho-methoxytoluene.

Devise a multistep synthesis for the following transformation.You may use any organic or inorganic reagents of your choice.Show the reagents necessary for each step and the product of each step.

What is the product of the following reaction?

Draw the product of the following reaction.

Draw meta-xylene.

Draw a mechanism for the following transformation.Include all lone pairs of electrons, curved arrows, and formal charges.

Which of these two molecules is more reactive in an SN1 reaction, and why?

Draw the product of the following reaction.

Draw the structure of styrene.

Devise a multistep synthesis for the following transformation.You may use any organic or inorganic reagents of your choice.Show the reagents necessary for each step and the product of each step.

Three alkylbenzene isomers of C10H14 undergo various reactions. Compound A reacts with KMnO4 to give a para substituted benzoic acid. Compound B does not react with KMnO4. Compound C reacts with KMnO4 to give benzoic acid. Propose structures for compounds A, B , and C .

Draw a Frost circle for pyrrole.Include and label all bonding molecular orbitals and antibonding molecular orbitals.Indicate the nonbonding energy level.Put the correct number of electrons in the appropriate orbitals in your drawing.

Which nitrogen in imidazole is more basic? Explain your answer.

In furan, what type of orbital do each of the two lone pairs on oxygen occupy?

Draw the structure of toluene.

The compound below is called benzofuran. Suggest an isomeric structure containing fused 5 -membered heterocycle. Does it obey the 4n +2 rule?

Which of these two molecules is more reactive in an SN2 reaction, and why?

Draw the structures of the following compounds and place them in the order of increasing boiling points: toluene, p-ethyltoluene, p-ethylbenzoic acid, p-diethylbenzene.

Which of these two molecules is more reactive in an S_N1 reaction, and why?

Three alkylbenzene isomers of C₁₀H₁₄ undergo various reactions. Compound A reacts with KMnO₄to give a para substituted benzoic acid. Compound B does not react with KMnO₄. Compound C reacts with KMnO₄ to give benzoic acid. Propose structures for compounds A, B , and C .

Which of these two molecules is more reactive in an S_N2 reaction, and why?