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a. Which of the following compounds have delocalized

Chapter 8, Problem 3P

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QUESTION:

a. Which of the following compounds have delocalized electrons?

1. \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\)

2. \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}=\mathrm{CHCH}_{2}\)

b. Draw the resonance contributors for the compounds that have delocalized electrons.

Equation Transcription:

Text Transcription:

CH_2 = CHCH_2 CH = CH_2

CH_3 CH = CHCH = CHCH_2

Questions & Answers

QUESTION:

a. Which of the following compounds have delocalized electrons?

1. \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\)

2. \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}=\mathrm{CHCH}_{2}\)

b. Draw the resonance contributors for the compounds that have delocalized electrons.

Equation Transcription:

Text Transcription:

CH_2 = CHCH_2 CH = CH_2

CH_3 CH = CHCH = CHCH_2

ANSWER:

Solution 3P:

Here, we are going to find the delocalized electrons for each compound.

Step 1:

Delocalized electrons in a molecule are defined as the number of electrons which are associated with the single atom or covalent bond.

It is generally represented by resonance structure.

Delocalized electrons result from the overlapping between the p-orbitals of two adjacent atoms.

(a) positive charge next to a π bond.

(b) positive charge next to an atom bearing lone pairs of electrons

(c) π bond next to an atom bearing lone pairs of electrons

Thus, among all the molecules, only (2), (4) and (5) have delocalization electrons.

On the other hand, molecule (1) does not have delocalization electron because pi electrons can not move towards sp3 carbon atom.

Similarly, molecules (3), (6) and (7) do not have delocalization electron because lone pair of  electrons can not move towards sp3 carbon atom.

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