ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 7, Problem 7.1P

Telfairine, a naturally occurring insecticide, and halomon, an antitumor agent, are two

polyhalogenated compounds isolated from red algae. (a) Classify each halide bonded to an sp 3

hybridized carbon as 1°, 2°, or 3°. (b) Label each halide as vinyl, allylic, or neither.

Chapter 7, Problem 7.1P, Problem 7.1 	Telfairine, a naturally occurring insecticide, and halomon, an antitumor agent, are two

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The halide bonded to sp3 hybridized carbon atom is to be classified as 1°, 2° or 3°.

Concept introduction: A halide is classified as 1°, 2° or 3° when it is bonded to primary, secondary or tertiary carbon atom, respectively. A primary, secondary and tertiary carbon atom is bonded to one, two and three carbon atoms, respectively.

Answer to Problem 7.1P

The halide bonded to sp3 hybridized carbon atom are classified as 1°, 2° and 3° as shown below.

ORGANIC CHEMISTRY, Chapter 7, Problem 7.1P , additional homework tip  1ORGANIC CHEMISTRY, Chapter 7, Problem 7.1P , additional homework tip  2

Explanation of Solution

The ball and stick model of telfarine and halomon shows that black balls represent carbon atom, white balls represent hydrogen atom, green and brown balls represent chlorine and bromine atom, respectively.

The actual structure of telfarine and halomon is shown in Figure 1.

ORGANIC CHEMISTRY, Chapter 7, Problem 7.1P , additional homework tip  3

Figure 1

A halide is classified as 1°, 2° or 3° when it is bonded to primary, secondary or tertiary carbon atom, respectively. A primary carbon atom is bonded to one other carbon atom and secondary carbon atom is bonded to two carbon atoms.

The 1°, 2° and 3° halides of telfarine are shown in Figure 2.

ORGANIC CHEMISTRY, Chapter 7, Problem 7.1P , additional homework tip  4

Figure 2

The 1°, 2° and 3° halides of halomon are shown in Figure 3.

ORGANIC CHEMISTRY, Chapter 7, Problem 7.1P , additional homework tip  5

Figure 3

Conclusion

The halide bonded to sp3 hybridized carbon atom are classified as 1°, 2° and 3° as shown in Figure 2 and Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: Each halide is to be labeled as vinyl, allylic or neither.

Concept introduction: In allyl halide, halogen atom is bonded to sp3 hybridized carbon atom which is bonded to sp2 carbon atom. The general formula of allyl halide is RCH=CHCH2X. In vinyl halide, halogen atom is directly bonded to sp2 hybridized atom.

Answer to Problem 7.1P

The allylic and vinyl halides of telfarine and halomon are shown below.

ORGANIC CHEMISTRY, Chapter 7, Problem 7.1P , additional homework tip  6

Explanation of Solution

In allyl halide, halogen atom is bonded to sp3 hybridized carbon atom which is bonded to sp2 carbon atom. The general formula of allyl halide is RCH=CHCH2X. In vinyl halide, halogen atom is directly bonded to sp2 hybridized atom. The halogen atom which is not bonded to allylic or vinylic carbon is written as neither.

The allylic and vinyl halides of telfarine and halomon are shown in Figure 4.

ORGANIC CHEMISTRY, Chapter 7, Problem 7.1P , additional homework tip  7

Figure 4

Conclusion

Each halide is labeled as allylic, vinyl and neither as shown in Figure 4.

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Chapter 7 Solutions

ORGANIC CHEMISTRY

Ch. 7 - Prob. 7.11PCh. 7 - Does the equilibrium favor the reactants or...Ch. 7 - Prob. 7.13PCh. 7 - Classify each solvent as protic or aprotic. a. b....Ch. 7 - Prob. 7.15PCh. 7 - Prob. 7.16PCh. 7 - Prob. 7.17PCh. 7 - Prob. 7.18PCh. 7 - Prob. 7.19PCh. 7 - Draw the product of each SN2 reaction and indicate...Ch. 7 - Prob. 7.21PCh. 7 - Prob. 7.22PCh. 7 - What happens to the rate of an SN1 reaction under...Ch. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Classify each carbocation as 1,2, or 3. a. b. c....Ch. 7 - Prob. 7.26PCh. 7 - Prob. 7.27PCh. 7 - Prob. 7.28PCh. 7 - Prob. 7.29PCh. 7 - Problem 7.30 For each alkyl halide and...Ch. 7 - Prob. 7.31PCh. 7 - Prob. 7.32PCh. 7 - Prob. 7.33PCh. 7 - Prob. 7.34PCh. 7 - Prob. 7.35PCh. 7 - Prob. 7.36PCh. 7 - Prob. 7.37PCh. 7 - Prob. 7.38PCh. 7 - Prob. 7.39PCh. 7 - Give the IUPAC name for each compound, including...Ch. 7 - Draw the products formed when each alkyl halide is...Ch. 7 - Give the IUPAC name for each compound. a. c. e. b....Ch. 7 - Prob. 7.43PCh. 7 - Draw the eight constitutional isomers having the...Ch. 7 - Which compound in each pair has the higher boiling...Ch. 7 - Draw the products of each nucleophilic...Ch. 7 - Prob. 7.47PCh. 7 - Rank the species in each group in order of...Ch. 7 - Which of the following nucleophilic substitution...Ch. 7 - Rank the species in each group in order of...Ch. 7 - Prob. 7.51PCh. 7 - Prob. 7.52PCh. 7 - 7.53 Consider the following reaction. Draw a...Ch. 7 - Prob. 7.54PCh. 7 - Draw the products of each SN2 reaction and...Ch. 7 - Prob. 7.56PCh. 7 - Prob. 7.57PCh. 7 - Consider the following SN1 reaction. a.Draw a...Ch. 7 - 7.59 Pick the reactant or solvent in each part...Ch. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Prob. 7.61PCh. 7 - Prob. 7.62PCh. 7 - Prob. 7.63PCh. 7 - Fluticasone, the chapter-opening molecule, can be...Ch. 7 - Prob. 7.65PCh. 7 - 7.66 Diphenhydramine, the antihistamine in...Ch. 7 - Draw a stepwise, detailed mechanism for the...Ch. 7 - When a single compound contains both a nucleophile...Ch. 7 - Prob. 7.69PCh. 7 - Prob. 7.70PCh. 7 - Draw a stepwise, detailed mechanism f or the...Ch. 7 - Prob. 7.72PCh. 7 - Fill in the appropriate reagent or starting...Ch. 7 - Devise a synthesis of each compound from an alkyl...Ch. 7 - Suppose you have compounds A-D at y our disposal....Ch. 7 - Muscalure, the sex pheromone of the common...Ch. 7 - Prob. 7.77PCh. 7 - Prob. 7.78PCh. 7 - Draw a stepwise mechanism for the following...Ch. 7 - 7.80 As we will learn in Chapter 9, an epoxide is...Ch. 7 - Prob. 7.81PCh. 7 - In some nucleophilic substitutions under SN1...
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