GOC Assignment 1

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