Bring the problem you’re stuck on.

Bring the lecture that lost you or the homework that isn’t working out. We’ll go through it with you, then show you how to approach the next one. Here is how that looks on a few problems, one from each course.

Taught by Gavin Brown and Felix Campbell, chemistry PhD students at the University of Arkansas.

Worked exampleOrganic Chemistry I, substitution

(R)-2-Bromobutane is treated with sodium cyanide in DMSO. Draw the product, including stereochemistry.

NCHH3CCH2CH3BrNCHCH3CH2CH3+Br−NaCNDMSO12(R)-2-bromobutane(S)-2-methylbutanenitrile
  1. Cyanide attacks the carbon from the side opposite bromine.
  2. The C–Br bond breaks as the new C–C bond forms. One step, no intermediate.

Backside attack inverts the stereocenter: (R) goes in, (S) comes out.

Inversion doesn’t always change the letter, so re-rank the groups every time.

The kind of problem students bring, marked up the way we’d go through it in a session.

More examples

One from each course we teach. Printed text is the question; blue is our working.

High school & AP Chemistry

A stoichiometry problem: turning a mass of fuel into a mass of product.

Request help with high school or AP

Sample problemStoichiometry

How many grams of CO2 form when 22.0 g of propane, C3H8, burns completely?

C3H8 + 5 O2 → 3 CO2 + 4 H2O

22.0 g×1 mol C3H844.10 g×3 mol CO21 mol C3H8×44.01 g1 mol CO2= 65.9 g CO2

Grams → moles → mole ratio → grams. The route is the same every time.

General Chemistry I & II

A weak-acid equilibrium: setting up the table, then checking the shortcut.

Request help with general chemistry

Sample problemWeak acids

What is the pH of 0.10 M acetic acid? (Ka = 1.8 × 10−5)

ICE table for acetic acid
CH3COOHH+CH3COO−
I0.1000
C−x+x+x
E0.10 − xxx

Ka =x20.10 − x≈x20.10= 1.8 × 10−5

x = √(1.8 × 10−6) = 1.34 × 10−3 M

pH = −log(1.34 × 10−3) = 2.87

Check the shortcut: x is 1.3% of 0.10. Under 5%, so dropping it was fair.

Organic Chemistry I & II

A short synthesis, planned backwards from the product.

Request help with organic chemistry

Sample problemSynthesis

Propose a synthesis of 2-butanone from trans-2-butene.

H2O, H2SO4PCC, CH2Cl2OHO

Work backwards. A ketone comes from a secondary alcohol, and the alcohol comes from adding water across the alkene. The alkene is symmetrical, so there is only one alcohol to make.

Got one of your own?

Tell us your course and the topics you’re working on. Your tutor will reply to confirm rates, timing and format.