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Compare the properties of propan-2-ol (I) and the

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 53SP Chapter 10

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 53SP

Compare the properties of propan-2-ol (I) and the hexafluoro analog (II).

(a) Compound II has almost triple the molecular weight of I, but II has a lower boiling point. Explain.

(b) Explain why the dipole moment of Compound II is much lower than the dipole moment of I, despite the presence of the six electronegative fluorine atoms.

(c) Why is II a stronger acid than I?

Step-by-Step Solution:
Step 1 of 3

Step-1

(a)

Molecular weight of Compound II is higher than that of compound I but the boiling point of compound II is lower, the reason behind this can be explained as follows:-

      It is known that in the absence of  other intermolecular force (van der waals force, dipole-dipole interaction or H-bond), the higher the molecular mass the greater the boiling point.So the boiling of compound II should be high. Here both the compound I and II have OH group and forms H-bond, but  the formation of H -bond in compound II is more difficult due to the presence of highly electronegative F substituents with greater electron clouds. So that the difference between the dipole moment among this two compound is also  very high.  Hence, even the molecular weight of compound II is large due to  the increase in vanderwaal’s forces the dipole moment of compound II is very small. It is known that dipole moment is directly proportional to the boiling point. Thus due to smaller dipole moment (0.32D), the boiling point of compound II is lower

Step-2

(b) The dipole moment of compound II is...

Step 2 of 3

Chapter 10, Problem 53SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

Organic Chemistry was written by and is associated to the ISBN: 9780321768414. This full solution covers the following key subjects: compound, moment, Lower, electronegative, dipole. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. The answer to “Compare the properties of propan-2-ol (I) and the hexafluoro analog (II). (a) Compound II has almost triple the molecular weight of I, but II has a lower boiling point. Explain.(b) Explain why the dipole moment of Compound II is much lower than the dipole moment of I, despite the presence of the six electronegative fluorine atoms.(c) Why is II a stronger acid than I?” is broken down into a number of easy to follow steps, and 64 words. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. Since the solution to 53SP from 10 chapter was answered, more than 466 students have viewed the full step-by-step answer. The full step-by-step solution to problem: 53SP from chapter: 10 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM.

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