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Chapter 2: Q2P (page 95)

The N-F bond is more polar than N-H bond, but NF3 has smaller dipole moment than NH3. Explain the curious result.

NH3: µ= 1.5 D, NF3: µ= 0.2D

Short Answer

Expert verified

N—F bond is more polar than N—H but, NF3 is less polar than NH3 because in NF3 individual polarity face towards F therefore net will cancel (since it is very less). But in NH3 N is more electronegative than H therefore this all add up and net is more.

Step by step solution

01

Step 1

Dipole moment in NH3 Dipole moment in NF3

In NH3, N is more electronegative than H. Therefore, N pulls the electrons from H towards itself and the direction of dipole moment due to the N-H bonds will be in the same direction as that of the lone pair of electrons on Nitrogen.

In NF3, F is more electronegative than N. Therefore, F atoms (all 3) pull the electrons towards themselves and the resultant moment is opposite to the directions of that of the lone pair of electrons on N atom. Therefore, the net dipole decreases(Dipole moment is a vector quantity).

NH3 dipole moment is much higher than that of NF3.

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Most popular questions from this chapter

Question: The pKa of ascorbic acid (vitamin C, page 9) is 4.17 , showing that it is lightly more acidic than acetic acid (CH3COOH, pKa = 4.74).

(a)Show four different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid.

(b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic.

(c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group

The following compound can become protonated on any of the three nitrogen atoms. One of these nitrogens is much more basic than the others, however.

  1. Draw the important resonance forms of the products of protonation on each of the three nitrogen atoms.
  2. Determine which nitrogen atom is the most basic.

Draw the hydrogen bonding that takes place between

(a) two molecules of ethanol.

(b) two molecules of propylamine.

(c) a molecule of dimethyl ether and two molecules of water.

(d) two molecules of trimethylamine and a molecule of water.

TheC=Odouble bond has a dipole moment of about 2.4Dand a bond length of about 1.23 Å.

  1. Calculate the amount of charge separation in this bond.
  2. Use this information to evaluate the relative importance of the following two resonance contributors:

(R is a general symbol for a carbon-containing group)

Consider each pair of bases, and explain which one is more basic. Draw their conjugate acids, and show which one is a stronger acid.

(a)

(b)

(c)

(d)
See all solutions

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