Tutorial 1: CHEM 2OA3 Fall 2010

1. Convert the following bond line structures into full format (showing all carbons and

hydrogens including the bonds between them)

O

OH

a) b) c)

d) e) f)

2. Give the hybridization of each of the indicate atoms in the following structures.

O

O

Ha

b

c

d N

Cl

ef

g

h

3. Indicate whether the following molecules are linear (1D), flat (2D) or 3D. Explain why.

A B C

H

ON

HH

4. Molecular orbital diagrams help rationalize bonding behaviour seen in molecules. Draw

and label a MO diagram for two hydrogen atoms combining to form H2.

5. Is it possible to make the dianion of H2 (H22-

by adding 2 electrons to H2)? Why or why

not – explain using a molecular orbital diagram.

6. Complete the Lewis structures for the compounds below, remember to show all lone

pairs shown as “:” There may be more than one answer to each.

A) B)

O B

H

C) At least 4 isomers of C2H4O2

7. Identify all the functional groups (ie 1o alcohols, ketones,) in the structure of Tamoxifen,

an antagonist of the estrogen receptor in breast tissue. Ph = phenyl (do not use

resonance forms of this phenyl ring)

ON

Is this compound different from Tamoxifen – why or why not.

ON

Draw at least 5 resonance structures starting from the compound shown. At least one

must be a zwitterion and at least one other must be a neutral compound. Which do you

think would be a fairly stable compound? Which would be more unstable?

Ph

Ph

NO+

Ph

8. Draw all the isomers of C4H10O and for any alcohols, label them primary, secondary and

tertiary alcohols, respectively.

9. Draw the following structures using bond line format:

3-chlorobutanoic acid

diethylmethylamine

2-bromo-1-butanol

3-chloro-3-methylpentane-2-one

10. Draw all possible constitutional isomers of C3H5Br

11. Much of organic chemistry hinges on the distribution of electrons within molecules.

Rank the following compounds with respect to thermodynamic stability (most stable on

the right, least stable on the left). Stability comes when charges are on more

electronegative atoms or are smeared out in space by induction (electron-withdrawing

groups – based on electronegativity) or resonance (charges can spread through a pi

bond.

H3C-

O-

O

O-

CH2-

O O-