John McMurry, Professor Emeritus

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Organic Chemistry

Chapter 6

Organic ChemistryChapter 6

Problem 6-1

(a)

Substitution

(b)

Elimination

(c)

Addition

Problem 6-2

(a)

Carbon is electrophilic.

(b)

Sulfur is nucleophilic.

(c)

Nitrogens are nucleophilic (for reasons that will be explained in Chapter 15).

(d)

Oxygen is nucleophilic; carbon is electrophilic.

Problem 6-3

A central boron atom labeled electrophilic, vacant p orbital bonded to three fluorine atoms.

Problem 6-4

Bromocyclohexane; chlorocyclohexane

Problem 6-5

A central carbon with a positive charge is bonded to three methyl groups.

The mechanism is shown in Figure 6.4

Problem 6-6

(a)

(b)

(c)

A carbon bonded to an oxygen ion, methyl group, chlorine atom, and methoxy group forms two products. Two arrows depict the movement of electrons, originating at the oxygen anion.

Problem 6-7

A reaction shows water, alkene, and hydronium ion reacting to form a product.

Problem 6-8

1-Chloro-2-methylpentane, 2-chloro-2-methylpentane, 3-chloro-2-methylpentane, 2-chloro-4-methylpentane, 1-chloro- 4-methylpentane

Problem 6-9

The mechanism for the formation of cyclopentane ring in prostaglandin H 2 radical.

Problem 6-10

Negative ΔG° is favored.

Problem 6-11

Larger K_eq is more exergonic.

Problem 6-12

Lower ΔG^‡ is faster.

Problem 6-13

Energy diagram shows large barrier to transition state, intermediate lower in energy than reactant, large barrier (higher than first) to second transition state, low energy product.

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- Authors: John McMurry, Professor Emeritus
- Publisher/website: OpenStax
- Book title: Organic Chemistry
- Publication date: Sep 20, 2023
- Location: Houston, Texas
- Book URL: https://openstax.org/books/organic-chemistry/pages/1-why-this-chapter
- Section URL: https://openstax.org/books/organic-chemistry/pages/chapter-6

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