Chem2O6 - 1997/98

1. Write the following condensed formulas as Lewis structures:

(i) (CH₃)₂CHNO₂     (ii) CH₃CNO     (iii) CH₃SO₃H     (iv) CHOCO₂H     (v) CH₃CHCHCOCl

2. (a) Which of the following molecules would you expect boron trifluoride (BF₃) to form a complex with?

(CH₃)₂CHCH₂CH₃    CH₃CH₂OCH₃    AlCl₃    CH₃NHCH₃    CH₃F

(b) Draw the Lewis structure of the complex.

(c) Which complex would you expect to be the most stable? Why?

3. Write resonance structures for the following, noting any structures which might be minor contributors.

(i) [CH₃CHOH]+     (ii) [CH₃CO₂H₂]+     (iii) [CH₃CHNH₂]+     (iv) [CH₂SO₂CH₃]-

4. Draw line structures for:

(i) isopropylcyclobutane
(ii) citric acid
(iii) 3-pentanone
(iv) 2-butanol

5. Complete the following reactions, indicating (where asked) the structure of any intermediates. Where appropriate, give the stereochemistry of the products.

11sep97