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 ${\text{sp}}^{\text{3}}$

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

Interpretation Introduction

(a)

Interpretation: The halide bonded to ${\text{sp}}^{\text{3}}$ 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 ${\text{sp}}^{\text{3}}$ hybridized carbon atom are classified as $1°$, $2°$ and $3°$ as shown below.

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.

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.

Figure 2

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

Figure 3

Conclusion

The halide bonded to ${\text{sp}}^{\text{3}}$ hybridized carbon atom are classified as $1°$, $2°$ and $3°$ as shown in Figure 2 and Figure 3.

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 ${\text{sp}}^{\text{3}}$ hybridized carbon atom which is bonded to ${\text{sp}}^{\text{2}}$ carbon atom. The general formula of allyl halide is $\text{RCH}=\text{CH}-{\text{CH}}_2\text{X}$. In vinyl halide, halogen atom is directly bonded to ${\text{sp}}^{\text{2}}$ hybridized atom.

Answer to Problem 7.1P

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

Explanation of Solution

In allyl halide, halogen atom is bonded to ${\text{sp}}^{\text{3}}$ hybridized carbon atom which is bonded to ${\text{sp}}^{\text{2}}$ carbon atom. The general formula of allyl halide is $\text{RCH}=\text{CH}-{\text{CH}}_2\text{X}$. In vinyl halide, halogen atom is directly bonded to ${\text{sp}}^{\text{2}}$ 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.

Figure 4

Conclusion

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