Organic Chemistry

Problems 57

sigma bonding molecular
orbital (p. 21)
single bond (p. 29)
tetrahedral bond angle (p. 28)

(s) tetrahedral carbon (p. 28)

trigonal planar carbon (p. 30)

triple bond (p. 32)

valence electrons (p. 7)

valence-shell electron-pair repulsion

(VSEPR) model (p. 24)

wave equation (p. 4)

wave functions (p. 4)

Problems

50. Draw a Lewis structure for each of the following species:

a. d. g.

b. e. h.

c. f. i.

51. Give the hybridization of the central atom of each of the following species, and tell whether the bond arrangement around it is
    linear, trigonal planar, or tetrahedral:
    a. d. g. HCN
    b. e. h.
    c. f. i.


52. Draw the condensed structure of a compound that contains only carbon and hydrogen atoms and that has
    a. three hybridized carbons.
    b. one hybridized carbon and two hybridized carbons.
    c. two hybridized carbons and two sphybridized carbons.


53. Predict the indicated bond angles:
    a. the bond angle in f. the bond angle in
    b. the bond angle in g. the bond angle in
    c. the bond angle in h. the bond angle in
    d. the bond angle in i. the bond angle in
    e. the bond angle in


54. Give each atom the appropriate formal charge:

a. c. e. g.

b. d. f. h.

55. Draw the ground-state electronic configuration for:

a. Ca b. c. Ar d.

56. Write the Kekulé structure for each of the following compounds:

a. c. e.

b. d. f.

57. Show the direction of the dipole moment in each of the following bonds (use the electronegativities given in Table 1.3):

a. c. e.

b. d. f.

58. What is the hybridization of the indicated atom in each of the following molecules?

a. c. e.

b. CH 3 CCH 3 d. CH 3 CN f. CH 3 OCH 2 CH 3

O

CH 3 CH CH 2 CH 3 CH 2 OH CH 3 CH NCH 3

CH 3 ¬Li I¬Br (CH 3 ) 2 N¬H

CH 3 ¬Br HO¬NH 2 CH 3 ¬OH

CH 3 OCH 3 (CH 3 ) 3 COH (CH 3 ) 2 CHCH(CH 3 )CH 2 C(CH 3 ) 3

CH 3 CHO CH 3 COOH CH 3 CH(OH)CH 2 CN

Ca^2 + Mg^2 +

CH 3 CH 3

H

N O

H

H

H B

H

H

HO HHN H

HH

H

N HHC C

CH 3

CH 3

HO CH 3 CH 3

C¬O¬H CH 3 OH

C¬O¬C CH 3 OCH 3 C¬C¬N CH 3 CH 2 NH 2

(CH 3 ) 2 N C¬C¬N CH 3 C N

+

C¬N¬C H 2

• BF
  C¬N¬C (CH 3 ) 2 NH F¬B¬F 4

C¬N¬H (CH 3 ) 2 NH H¬C¬H H 2 C“O

sp^3

sp^3 sp^2

sp^3

• CH 3 +CH 3 H 3 O+

BH 3 +NH 4 C(CH 3 ) 4

NH 3 CH 3

H 2 CO CH 3 N 2 + H 2 NO-

CO 3 2 - CH 3 NH 2 NO+

H 2 CO 3 N 2 H 4 CO 2