Deduce the structure of an unknown compound with the molecular formula C10H14O and the following proton NMR data: F1F1F1S1F1F1F10 7.39 (d, 2H, J = 7 Hz), 6.93 (d, 2H, J = 7 Hz), 3.81 (s, 3H), 2.87 (septet, 1H, J = 6.8 Hz), 1.20 (d, 6H, J = 6.8 Hz).

First calculate the degree of unsaturati

Devise a two-step synthesis to form the product from benzene. The intermediate is a substituted benzene with a 1H NMR singlet at F1F1F1S1F1F1F10 2.5 ppm. Identify the intermediate.

Both an acyl and nitro group are meta di

Select the correct name for PhCH2Br.

A) bromobenzene B) bromobenzyl C) phenyl bromide D) benzyl bromide A) bromobenzene B) bromobenzyl C) phenyl bromide D) benzyl bromide

Exam 16: The Chemistry of Benzene and Its Derivatives

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Indicate whether the compound should undergo nitration more rapidly or more slowly than benzene and give the structure of the major mononitration product. Explain, using a few words and structures.

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Question 1

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The benzene ring has an alkyl substituent, so it will react faster than benzene. An alkyl group is an ortho/para director. The para isomer will predominate over the ortho isomer due to the steric hindrance of the bulky tert-butyl group.

Indicate whether the compound should undergo nitration more rapidly or more slowly than benzene and give the structure of the major mononitration product. Explain, using a few words and structures.

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Question 2

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The boron is inductively withdrawing and destabilizing, so it will react slower than benzene. It will be a meta director since ortho/para substitution would give a very unstable intermediate.
The major product is:

Draw the major organic product for the reaction.

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Question 3

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This will be an intramolecular Friedel-Crafts alkylation. The first step is protonation of the alkene by sulfuric acid to form a tertiary carbocation. The carbocation will then react with the ring, then the benzene ring will be regenerated.

Give the IUPAC name for the compound.

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Question 4

Which compound reacts slowest during nitration?

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Question 5

Deduce the structure of an unknown compound with the molecular formula C₁₀H₁₄O and the following proton NMR data:  7.39 (d, 2H, J = 7 Hz), 6.93 (d, 2H, J = 7 Hz), 3.81 (s, 3H), 2.87 (septet, 1H, J = 6.8 Hz), 1.20 (d, 6H, J = 6.8 Hz).

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Question 6

Provide detailed, arrow-pushing mechanisms for the transformation. Show all reactive intermediates. (It is not necessary to show every resonance structure for appropriate intermediates.)

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Question 7

Devise a two-step synthesis to form the product from benzene. The intermediate is a substituted benzene with a ¹H NMR singlet at  2.5 ppm. Identify the intermediate.

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Question 8

Which of these statements is not true about the electrophilic bromination of benzene?

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Question 9

Write a mechanism for this reaction. Show the formation of major product (in ortho and para situations, just show one, not both). Using structures, and 10 words or less, explain clearly why substitution occurs in the position you indicated over any of the other positions.

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Question 10

Draw the major organic product for the reaction. The product should be one compound with 11 carbons.

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Question 11

For each set, circle the faster of the two reactions. a. b.

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Question 12

Which compound would be the most reactive towards ring bromination?

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Question 13

Write a mechanism for this reaction. Show the formation of major product (in ortho and para situations, just show one, not both). Using structures, and 10 words or less, explain clearly why substitution occurs in the position you indicated over any of the other positions.

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Question 14

Explain how you would distinguish between three isomers with the molecular formula C₉H₁₂ using only ¹H NMR spectroscopy.

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Question 15

Select the correct name for PhCH₂Br.

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Question 16

The -NH₂ group is an ortho/para-director. So, explain why the reaction is observed experimentally. Use structures and 15 words or less.

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Question 17

Give the IUPAC name for the compound.

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Question 18

A reaction forms the ortho, meta, and para isomers of dibromobenzene. Draw the structures of the three compounds and explain how you can use the melting point to separate the mixtures. Which would you expect to have the highest melting point?

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Question 19

Indicate the missing products of the reaction. When filling in the product indicate only the major organic product(s). There may be more than one acceptable answer. If you believe no reaction would occur, write NR. Denote stereochemistry where appropriate.

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Question 20

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Exam 16: The Chemistry of Benzene and Its Derivatives

Indicate whether the compound should undergo nitration more rapidly or more slowly than benzene and give the structure of the major mononitration product. Explain, using a few words and structures.

Indicate whether the compound should undergo nitration more rapidly or more slowly than benzene and give the structure of the major mononitration product. Explain, using a few words and structures.

Draw the major organic product for the reaction.

Give the IUPAC name for the compound.

Which compound reacts slowest during nitration?

Deduce the structure of an unknown compound with the molecular formula C10H14O and the following proton NMR data:  7.39 (d, 2H, J = 7 Hz), 6.93 (d, 2H, J = 7 Hz), 3.81 (s, 3H), 2.87 (septet, 1H, J = 6.8 Hz), 1.20 (d, 6H, J = 6.8 Hz).

Provide detailed, arrow-pushing mechanisms for the transformation. Show all reactive intermediates. (It is not necessary to show every resonance structure for appropriate intermediates.)

Devise a two-step synthesis to form the product from benzene. The intermediate is a substituted benzene with a 1H NMR singlet at  2.5 ppm. Identify the intermediate.

Which of these statements is not true about the electrophilic bromination of benzene?

Write a mechanism for this reaction. Show the formation of major product (in ortho and para situations, just show one, not both). Using structures, and 10 words or less, explain clearly why substitution occurs in the position you indicated over any of the other positions.

Draw the major organic product for the reaction. The product should be one compound with 11 carbons.

For each set, circle the faster of the two reactions. a. ​ b.

Which compound would be the most reactive towards ring bromination?

Write a mechanism for this reaction. Show the formation of major product (in ortho and para situations, just show one, not both). Using structures, and 10 words or less, explain clearly why substitution occurs in the position you indicated over any of the other positions.

Explain how you would distinguish between three isomers with the molecular formula C9H12 using only 1H NMR spectroscopy.

Select the correct name for PhCH2Br.

The -NH2 group is an ortho/para-director. So, explain why the reaction is observed experimentally. Use structures and 15 words or less.

Give the IUPAC name for the compound.

A reaction forms the ortho, meta, and para isomers of dibromobenzene. Draw the structures of the three compounds and explain how you can use the melting point to separate the mixtures. Which would you expect to have the highest melting point?

Indicate the missing products of the reaction. When filling in the product indicate only the major organic product(s). There may be more than one acceptable answer. If you believe no reaction would occur, write NR. Denote stereochemistry where appropriate.

Chemical Bonding and Chemical Structure

Alkanes and Organic Nomenclature

The Curved-Arrow Notation, Resonance, Acids and Bases, and Chemical Equilibrium

Introduction to Alkenes and Alkynes

Addition Reactions of Alkenes and Alkynes

Principles of Stereochemistry

Cyclic Compounds and Reaction Stereochemistry

Nomenclature and Noncovalent Intermolecular Interactions

The Chemistry of Alkyl Halides

Free-Radical Reactions, Main-Group Organometallic Compounds, and Carbenes

The Chemistry of Alcohols and Thiols

The Chemistry of Ethers, Epoxides, Glycols, and Sulfides

Introduction to Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Dienes and Aromaticity

Allylic and Benzylic Reactivity

The Chemistry of Aryl Halides, Vinylic Halides, and Phenols

The Chemistry of Aldehydes and Ketones

The Chemistry of Carboxylic Acids

The Chemistry of Carboxylic Acid Derivatives

The Chemistry of Enolate Ions, Enols, and Α,β-Unsaturated Carbonyl Compounds

The Chemistry of Amines

Carbohydrates

The Chemistry of Thioesters, Phosphate Esters, and Phosphate Anhydrides

The Chemistry of the Aromatic Heterocycles and Nucleic Acids

Amino Acids, Peptides, and Proteins

Pericyclic Reactions

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Deduce the structure of an unknown compound with the molecular formula C₁₀H₁₄O and the following proton NMR data:  7.39 (d, 2H, J = 7 Hz), 6.93 (d, 2H, J = 7 Hz), 3.81 (s, 3H), 2.87 (septet, 1H, J = 6.8 Hz), 1.20 (d, 6H, J = 6.8 Hz).

Devise a two-step synthesis to form the product from benzene. The intermediate is a substituted benzene with a ¹H NMR singlet at  2.5 ppm. Identify the intermediate.

For each set, circle the faster of the two reactions. a. b.

Explain how you would distinguish between three isomers with the molecular formula C₉H₁₂ using only ¹H NMR spectroscopy.

Select the correct name for PhCH₂Br.

The -NH₂ group is an ortho/para-director. So, explain why the reaction is observed experimentally. Use structures and 15 words or less.