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Which compound has a longer C—Cl bond?

Chapter 1, Problem 68P

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QUESTION:

Which compound has a longer \(C-C l\) bond?

             \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}\)                                                                                                      \(\mathrm{CH}_{2}=\mathrm{CHCl}\)

at one time it was used as a                        used as the starting material

        refrigerant, an anesthetic, and a                        for the synthesis of a plastic that

propellant for aerosol sprays                          is used to make bottles, ooring,

                                                            and clear packaging for food

Equation Transcription:

Text Transcription:

C-Cl

CH_3 CH_2 Cl

CH_2 = CHCl

Questions & Answers

QUESTION:

Which compound has a longer \(C-C l\) bond?

             \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}\)                                                                                                      \(\mathrm{CH}_{2}=\mathrm{CHCl}\)

at one time it was used as a                        used as the starting material

        refrigerant, an anesthetic, and a                        for the synthesis of a plastic that

propellant for aerosol sprays                          is used to make bottles, ooring,

                                                            and clear packaging for food

Equation Transcription:

Text Transcription:

C-Cl

CH_3 CH_2 Cl

CH_2 = CHCl

ANSWER:

Solution:

Here we have to find the longer C-Cl bond length among the given molecule i.e CH3CH2Cl and CH2=CHCl

Step 1

From the concept of hybridization , it is known that,  more the s-character, shorter and stronger will be the bond.

 In case of  CH3CH2Cl, in the C-Cl bond , the C -atom is sp3 hybridized and the Cl-atom is also sp3 hybridized. Thus the bond will form by the overlapping of  two sp3 hybridized orbital (s-character 25%).

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