Chap 2: Các hiệu ứng điện tử trong hóa hữu cơ

Nội dung 1: Use the + and  to indicate the direction of expected polarity for each of the
bonds indicated

Bài 1. Write + and  by the appropriate atoms and draw a dipole moment vector for any of the
following molecules that are polar:
(a) HF (b) IBr (c) Br2 (d) F2

Solution

Bài 2. For each compound below, identify any polar covalent bonds and indicate the direction of
the dipole moment using the symbols + and :
(a) HBr (b) HCl (c) H2O (d) CH4O

Solution
a) b) c) d)

Bài 3. Consider the structure of methanol. Identify all polar covalent bonds and show any partial
charges that result from inductive effects:

Solution
STEP 1: Identify all polar covalent bonds.
STEP 2: Determine the direction of each dipole

STEP 3: Indicate the location of partial charges.

Bài 4. For each of the following compounds, identify any polar covalent bonds by drawing +
and  symbols in the appropriate locations:

Solution
a)
b)

c)

d)

e)

f)

Bài 5. Using a three-dimensional formula, show the direction of the dipole moment of CH 3OH.
Write + and  signs next to the appropriate atoms.
Solution

Bài 6. The regions of + in a compound are the regions most likely to be attacked by an anion,
such as hydroxide (HO-). In the compound below, identify the two carbon atoms that are
most likely to be attacked by a hydroxide ion:

Solution

Bài 7. Use the + and  convention to indicate the direction of expected polarity for each of the
bonds indicated.
(a) H3C–Cl (b) H3C–NH2 (c) H2N–H
(d) H3C–SH (e) H3C–MgBr (f) H3C–F

Solution
Nội dung 2: Use the electronegativity values shown in the table to rank the following bonds
from least polar to most polar

Figure 2.2. Electronegativity values of elements

Bài 1. Which element in each of the following pairs is more electronegative?
(a) Li or H (b) B or Br (c) Cl or I (d) C or H
Solution
(a) H (b) Br (c) Cl (d) C
Bài 2. Use the electronegativity values shown in Figure 2-2 to rank the following bonds from
least polar to most polar: H3C–Li, H3C–K, H3C–F, H3C–MgBr, H3C–OH
Solution

Bài 3. Identify the most electronegative element in each of the following molecules:
(a) CH2FCl (b) FCH2CH2CH2Br
(c) HOCH2CH2NH2 (d) CH3OCH2Li
Solution

Bài 4. Use the electronegativity table given in Figure 2-2 to predict which bond in each of the
following pairs is more polar, and indicate the direction of bond polarity for each compound.
(a) H3CCl or ClCl (b) H3CH or HCl
(c) HOCH3 or (CH3)3SiCH3 (d) H3CLi or LiOH
Solution
Bài 5. For each pair of compounds below, identify the one that would be expected to have more
ionic character. Explain your choice.
(a) NaBr or HBr (b) BrCl or FCl

Solution
a) b)
NaBr > HBr FCl > BrCl
Bài 6. Which bond is more polar: HCl or HO
Solution

Bài 7. Which of the following bonds are the most polar, that is, have the greatest ionic
character: HBr, NH, NO, PCl
Solution
Bài 8. Which is the most polar bond: CS, CP, PO, or OF?
Solution

Bài 9. Arrange the following bonds in terms of increasing ionic character:

CH, FH, NaCl, BrH, KF.
Solution
CH < FH < BrH < NaCl < KF
Nội dung 3: Predicting the direction of a Dipole Monment

Bài 1. Although molecules of CO2 have polar bonds (oxygen is more electronegative than
carbon), carbon dioxide has no dipole moment. What can you conclude about the geometry
of a carbon dioxide molecule?
Solution

Bài 2. Boron trifluoride (BF3) has no dipole moment ( = 0 D). Explain how this observation
confirms the geometry of BF3 predicted by VSEPR theory.
Solution

Bài 3. Tetrachloroethene (CCl2=CCl2) does not have a dipole moment. Explain this fact on the
basis of the shape of CCl2=CCl2.
Solution

Bài 4. Sulfur dioxide (SO2) has a dipole moment ( = 1.63 D); on the other hand, carbon
dioxide (has no dipole moment ( = 0 D). What do these facts indicate about the geometry of
sulfur dioxide?
Solution
Bài 5. Trichloromethane (CHCl3, also called chloroform) has a larger dipole moment than
CFCl3. Use three-dimensional structures and bond moments to explain this fact.
Solution

Bài 6. Explain why cis-1,2-dichloroethene (Table 2.2) has a large dipole moment whereas trans-
1,2-dichloroethene has a dipole moment equal to zero.
Solution

Bài 7. Indicate the direction of the important bond moments in each of the following
compounds (neglect Ci H bonds). You should also give the direction of the net dipole
moment for the molecule. If there is no net dipole moment, state that  = 0 D.

(a) cis-CHF=CHF (b) trans-CHF=CHF (c) CH2=CF2 (d) CF2=CF2

Solution
Bài 8. Write structural formulas for all of the alkenes with (a) the formula C 2H2Br2 and (b) the
formula C2Br2Cl2. In each instance designate compounds that are cis–trans isomers of each
other. Predict the dipole moment of each one.
Solution

Bài 9. If the dipole moment of CH3F is 1.847 D and the dipole moment of CD3F is 1.858 D,
which is more electronegative, hydrogen or deuterium?
Solution

Bài 10. Which of the following molecules would you expect to have a dipole moment of zero?

Solution
Bài 11. Identify whether each of the following compounds exhibits a molecular dipole moment.
If so, indicate the direction of the net molecular dipole moment:

(a) CH3CH2OCH2CH3 (b) CO2

Solution
STEP 1: Predict the molecular geometry.

STEP 2: Identify the direction of all dipole moments.

STEP 3: Draw the net dipole moment

b)

Bài 12. Identify whether each of the following compounds exhibits a molecular dipole moment.
For compounds that do, indicate the direction of the net molecular dipole moment:
Solution
a) b) c)

a) e) f)

h) i)

j) k)

l)
Bài 13. Which of the following compounds has the larger dipole moment? Explain your
choice: CHCl3 or CBrCl3
Solution:

Bài 14. Which of these molecules are polar? For each that is polar, specify the direction of its
polarity.
(a) CH3Cl (b) CH2O (c) C2H2
Solution

Bài 15. Make a three-dimensional drawing of methylamine, CH3NH2, a substance responsible for
the odor of rotting fish, and show the direction of its dipole moment ( = 1.31)
Solution

Bài 16. Ethylene glycol, HOCH2CH2OH, may look nonpolar when drawn, but an internal
hydrogen bond results in an electric dipole moment. Explain.
Solution
Bài 17. Make three-dimensional drawings of the following molecules, and predict whether each
has a dipole moment. If you expect a dipole moment, show its direction.
(a) H2C=CH2 (b) CHCl3 (c) CH2Cl2 (d) H2C=CCl2
Solution

Bài 18.Which of the following molecules has a dipole moment? Indicate the expected direction
of each.

Solution

Bài 19. Phosgene, Cl2C5O, has a smaller dipole moment than formaldehyde, H 2C5O, even though
it contains electronegative chlorine atoms in place of hydrogen. Explain.
Solution
Bài 20. Fluoromethane (CH3F,  = 1.81 D) has a smaller dipole moment than chloromethane
(CH3Cl,  = 1.87 D) even though luorine is more electronegative than chlorine. Explain.
Solution

Bài 21. Methanethiol, CH3SH, has a substantial dipole moment ( = 1.52 D) even though carbon
and sulfur have identical electronegativities. Explain.
Solution

Bài 22. Which compound has a larger dipole moment, CHCl3 or CH2Cl2?
Solution

Bài 23. The following compound has two isomers. One isomer has a dipole moment of 0 D,
whereas the other has a dipole moment of 2.95 D. Propose structures for the two isomers that
are consistent with these data.
ClCH=CHCl
Solution
 Nội dung 3: Công thức cộng hưởng – Điện tích hình thức

Bài 1. Which sets are pairs of acceptable resonance contributing structures?

S T R AT E G Y
The concept being examined here is that resonance involves the redistribution of valence
electrons; the connectivity of atoms does not change.
SOLUTION
a) A pair of resonance contributing structures. They differ only in the distribution of valence
electrons.
b) Not a pair of resonance contributing structures. They differ in the arrangement of their atoms.
Oxygen is bonded to a hydrogen atom in the Lewis structure on the right, but the other
structure contains no such bond.

Bài 2. Which sets are pairs of resonance contributing structures?

Solution: Pair (a) only

Bài 3. Draw the resonance contributing structure indicated by the curved arrows. Be certain to
show all valence electrons and all formal charges
 S T R AT E G Y
Any curved arrow that points to an atom will generate a lone pair of electrons. Any curved
arrow that points to a bond will result in an additional bond on top of the original bond. That
is, a single bond will become a double bond and a double bond will become a triple bond.

SOLUTION

Bài 4. Use curved arrows to show the redistribution of valence electrons in converting
resonance contributing structure (a) to (b) and then (b) to (c). Also show, using curved
arrows, how (a) can be converted to (c) without going through (b).

Solution
Bài 5. Write the resonance structure that would result from moving the electrons as the curved
arrows indicate. Be sure to include formal charges if needed.

Solution
Bài 6. Add any missing unshared electron pairs (if any), then, using curved arrows to show the
shifts in electrons, write the contributing resonance structures and resonance hybrid for each
of the following:

Solution
Bài 7. For each set of resonance structures that follow, add a curved arrow that shows how
electrons in the left formula shift to become the right formula, and designate the formula that
would contribute most to the hybrid. Explain your choice:

Solution
Bài 8. Write the resonance structure that would result from moving the electrons in the way
indicated by the curved arrows.

Solution

Bài 9. Show the curved arrows that would convert A into B

Solution
Bài 10. For the following write all possible resonance structures. Be sure to include formal
charges where appropriate.

Solution
Bài 11. Assign the proper formal charge to the colored atom in each of the following structures:

Solution

Bài 12. Add any unshared electrons to give each element an octet in its valence shell in the
formulas below and indicate any formal charges. Note that all of the hydrogen atoms that are
attached to heteroatoms have been drawn if they are present.
Solution

Bài 13. Consider a chemical species (either a molecule or an ion) in which a carbon atom forms
three single bonds to three hydrogen atoms and in which the carbon atom possesses no other
valence electrons.
(a) What formal charge would the carbon atom have?
(b) What total charge would the species have?
(c) What shape would you expect this species to have?
(d) What would you expect the hybridization state of the carbon atom to be?

Solution
Bài 14. Consider a chemical species like the one in the previous problem in which a carbon atom
forms three single bonds to three hydrogen atoms, but in which the carbon atom possesses an
unshared electron pair.
(a) What formal charge would the carbon atom have?
(b) What total charge would the species have?
(c) What shape would you expect this species to have?
(d) What would you expect the hybridization state of the carbon atom to be?

Solution

Bài 15. Consider another chemical species like the ones in the previous problems in which a
carbon atom forms three single bonds tothree hydrogen atoms but in which the carbon atom
possesses a single unpaired electron.
 (a) What formal charge would the carbon atom have?
(b) What total charge would the species have?
(c) Given that the shape of this species is trigonal planar, what would you expect the
hybridization state of the carbon atom to be?

Bài 16. For each of the structures below, draw the resonance structure that is indicated by
the curved arrows. Be sure to include formal charges.

Solution
a)
b)

c)

d)

e)

f)
g)

h)

Bài 17. In each case below, draw the curved arrow(s) required in order to convert the first
resonance structure into the second resonance structure. In each case, begin by drawing all
lone pairs and then use the formal charges to guide you.

Solution
a)
b)

c)

d)

Bài 18. For each of the compounds below, locate the pattern we just learned (lone pair next to a
p bond) and draw the appropriate resonance structure:
Solution
a)

b)

c)

d)

e)
f)

g)

h)
Bài 19. Draw the resonance structure(s) for each of the compounds below:

Solution
a)

b)

c)

d)
Bài 20. For each of the compounds below, locate the lone pair adjacent to a positive charge
and draw the resonance structure:

Solution
a)

b)

c)

Bài 21. Draw resonance structures for each of the following compounds:
Solution
a)

b)

c)

d)

e)
f)

g)

h)

i)
Bài 22. Draw all significant resonance structures for each of the following compounds:

Solution

a)

b)
c)

d)

e)

f)
g)

h)

i)

i)
k)

f)

Bài 23.Use resonance structures to help you identify all sites of low electron density (+) in the
following compound:

Solution
Bài 24. Use resonance structures to help you identify all sites of high electron density (-) in the
following compound:

Solution
Bài 25. Draw resonance structures for each of the following:

a)

b)
c)

d)

e)
f)
g)

h)
i)

j)