CHEM 205 Worksheet (WS1) 46 Points Total

Key Topics: Lewis Structures, Formal Charge, Resonance, Hybridization, Functional Group Identity

1. For each molecular formula below, draw a valid Lewis structure (bond-line structure also fine). Each
atom should be neutral and obey the octet rule. Show lone electron pairs where applicable. It will be
helpful to determine the degrees of unsaturation first (total number of pi-bonds and/or rings possible)
(2pts for each correct structure).

(a) C5H11OBr (b) C6H12 (c) C2H3N

2. For the molecular formula below, draw all unique constitutional isomers that are also valid structures
and also contain at least one CH3 group. Each atom should be neutral and obey the octet rule. Show lone
electron pairs where applicable. It will be helpful to determine the degrees of unsaturation first (total
number of pi-bonds and/or rings possible) (2pts for each correct structure)

C3H6Br2

3. On each line below, write the generic functional group being highlighted by each box. Do not name the
compound, just indicate the functional group being highlighted.
(2pts for each functional group identified correctly)

(b) (c)
(a) OH
O
HO
O OH

N 3

O (e) CN
(d)

N
4. Identify the hybridization state and geometry (not shape) for each atom indicated by an arrow in the
structure below. (1pt for each correct hybridization, 1pt for each correct geometry)

CN O B

5. For each structure below, draw the best additional resonance structures. The number of additional
resonance structures that you need to draw are indicated by the number of resonance arrows in each
bracket, for a given structure. It would be helpful to show any missing lone electron pairs. Don’t forget to
include formal charge where applicable.
(2pts for each correct resonance structure)

(a)
O

(b)
H
O N

(c)