CHM 1321 A

Assignment 1 Answers
1) Draw Lewis structures for the following molecules:
(a) CH3NH2 (b) CH2CH2 (c) C2H2
H H H H C C H
H C N H C C
H H H H
(d) CH3CH2CHO (e) CH3CH2OH2+ (f) (CH3)3N
H H H H H H
O H C N C H
H C C C H C C O H H C H
H H H H H H H H
H
(g) CH3CN (h) CH3CH(OH)CH3 (i) CH3NCO
H H H
H C C N H O H H C N C O
H H C C C H H
H H H
(j) CH2CHCH(OH)CH2CO2H (k) NCCH2COCH2CHO (l) CH3CH(CH3)CH2C(CH2CH3)2CHO
H
H H H H O H O H O
H C H
C C C C C N C C C C C
H H C H
H O H O H H H
H H H O
H
H C C C C C
H C H H
H H
H
H C H
H C H
H
(m) (CH3)3C+ (n) CH3CH2O- (o) CH3CHCHCH2CHCHCO2H
H H H H H H H H H O
H C H H C C O H C C C C C C C
H H H O H
H H
H C C
H
H C H
H
(p) HC(O)N(CH3)2 (q) [(CH3)2CHN(CH3)3]+ (r) [CH3C(OH)CH3]+ (two structures)
H H H
O H H
C H H C H O O
C H H H H H H H
H N
C H H C C N C H H C C C H H C C C H
H H H C HH H H H H
H
H C HH
H
(s) [(CH3CH2)2O(CH3)]+ (t) [CH3CNH]+ (two (u) [CH3CH2CHCHCH2]- (two
structures) structures)
 H H
H H H H H H H H
H C C N
H C C O C C H H C C C C C
H
H H H H H H H H
H C H H H
H H H H H
H C C N
H C C C C C
H
H H H H
(v) [CH3CH2CHCHCH2]+ (w) [CH3CH2]- (x) HNO3
(two structures) H H
O
H H H H H C C
H N
H C C C C C H H O O
H H H H

H H H H
H C C C C C
H H H H
y) H2SO4 z) HNO2 aa) CH3SO2Cl
O H N H O
H O S O H O O H C S Cl
O H O
bb) HSO3- cc) SO3 dd) NaN3
O O
Na Na
H S S O
O O
O N N N or N N N

2) Draw all of the structures in question 1 using line notation.

(a) CH3NH2 (b) CH2CH2 (c) C2H2
NH2
(d) CH3CH2CHO (e) CH3CH2OH2+ (f) (CH3)3N
O
OH2 N
(g) CH3CN (h) CH3CH(OH)CH3 (i) CH3NCO
N OH N N
or C
O O
(j) CH2CHCH(OH)CH2CO2H (k) NCCH2COCH2CHO (l) CH3CH(CH3)CH2C(CH2CH3)2CHO
O O O
N
OH OH O

(m) (CH3)3C+ (n) CH3CH2O- (o) CH3CHCHCH2CHCHCOOH

OH
O
O
(p) HC(O)N(CH3)2 (q) [(CH3)2CHN(CH3)3]+ (r) [CH3C(OH)CH3]+ (two structures)
O H H
N O O
N
 (s) [(CH3CH2)2O(CH3)]+ (t) [CH3CNH]+ (two (u) [CH3CH2CHCHCH2]- (two
structures) structures)
O H
N

H
N

(v) [CH3CH2CHCHCH2]+ (w) [CH3CH2]- (x) HNO3

(two structures)
O
H N
O O

y) H2SO4 z) HNO2 aa) CH3SO2Cl

O H N O
O O
H O S O H H 3C S Cl
O O
bb) HSO3- cc) SO3 dd) NaN3
O O
Na Na
H S S O
O O
O N N N or N N N

3) There is a small portion of the periodic table that you must know to do organic chemistry.
Construct this from memory including the group numbers, bonds for neutral atoms and
numbers of valence electrons.
I

H11 III IV V VI VIII

B3 3 C4 4 N5 3 O62 F7 1

Si4 P5 S6 Cl7

Br7

valence electrons in blue I7

bonds in red

4) Convert the following to Lewis structures:

 O
O Br
OH O
a) b) c)
O O
H H O H
H Br
H C H H C C H C H H O
H C H H H C C OH
H C C C C C C O C H
C C C C C C O C C
H C H H C HH H O H H
H C HH H H H H
H H
H

N e) CN f)
d) O OH
H O
H C H
H H H H O H H H H H H H H H
H C C O C C N C C C H H C C C C C N H C C C C C C C O H
H H H H H H H H H H H H H H
H C H
H

5) Draw all of the structures in question 4 using condensed notation.

O
O Br
OH O
a) b) c)
O O
C6H5CO2H
or
(CH3)CHCHCHCOCHBrCH2OCHO
(CH3)2CCHCH2CH2CHCH3CHO CHCHCHCHCHCHCO2H

N e) CN f)
d) O OH
O
CH3CH2CH2CH2CN CH3CH2CCCHCHCH2OH
CH3CH2OCH2CH2NCH3COCH(CH3)2
6) Show the direction of the dipole moments of the following bonds.
+  -
-
+ - - + +
C Cl C H C N C O
(a) C-Cl (b) C-H (c) C-N (d) C-O (e)
- - + + 
-
 +

-
 +
C B N H O H C Br

C-B (f) N-H (g) O-H (h) C-Br

7) Provide molecular formulas for each of the following.

 OH
O O CO2H
O
a) H b) OH c) d) O
HO O
OH
C7H12O C7H6O2 O C15H20O7
C19H28O2
O
HN O O
H H
e) f) N N
N OH
N N N H
O O
OH
C13H23N3O6
C15H14N4O

8) Convert the following to Lewis structures

H c)
O H N
O C
O H
a) O b) H C H
C C
H
C C
Br H C H H C H
Br H H H H
H H H O H
H C C N C C H
H C C C C O C H
H H H
H H H H C H
H
O
e) OH H
d) f)
N H H O H
H H C C C C H
H H O H H C H H H H
H H H H
H C C C N C H
H C C C C C H
H H H
H C H H H H H
H
NH2 O NO2
g) h) i)
H O
O
H C N
C C
H
H O H H H C C
H N C H
H H C C C C C H
H C H C H
C C H H H H H H H
H C C H
C
H H
H H
F F k) l)
j) BF2 B
O
H H O H
H C C C C H H H H H
H H H H C C C C C H H C C C C C H
H H H H H H H H H H
9) Draw each of the open-chain molecules in question 8 as condensed structures.
O
O
d)
a) c) N N
O

[CH3CH2CHCO2CH3]- [((CH3)2CH)2N]- CH3CH2CON(CH3)2

OH O
e) f) h)

[(CH3CH2)2CCH3]+ [CH3CH2COHCH3]+ [CH3CHCOCH2CH3]-

l)
j) k)
BF2
O

[CH3CH2C(OBF2)CH3]+ [CH3CHCHCHCH3]+ [CH3CHCHCHCH3]-

10) Each of the following molecules carries a charge (+ or -). Identify the charged atom in each of
them.

11) Each of the following molecules carries a charge (+ or -). At each charge site, draw the full
Lewis structure to account for the charge.
O O N
a) b) C H c) d) N
C N O C
H

O
O Br N
S O
e) O f) g)
C C
H3CO H F
OCH3
12) Redraw the following molecules showing the indicated functional group in expanded Lewis
form.
 example:
O O H
H
C C
O O H

O O O
N O H H
C N S C S N
a) b) O c) H d) C
O H
N N O

OH OH
or
e) C f)
N N O H O H
C C C C
O N C N O N C N
H H H N H N
O O