ATTN: answers to the below questions are due at the start of your second meeting (1/11 or 1/12); these answers should be part of your pre-lab write-up. The first quiz will be administered in lecture on Tuesday 1/16/2007. Please make sure that you arrive on time.

Important announcement: The lecture was moved to CS24.

1. Referring to step 2, answer the following questions.

a. Methanol is used as solvent in the reaction. Rationalize this choice.

b. Why it is important to dissolve the sodium hydroxide completely before proceeding? Provide a balanced equation for this step.

c. Formaldehyde is the electrophile in the reaction. How is it introduced into the reaction and which precuation should be taken handling it?

d. After the reaction is completed, the reaction mixture (usually a brownish oil) is poured in water and the mixture then acidified. Explain briefly and provide pertinent chemical equations.

e. Many students observe a viscous liquid as their crude product. Explain briefly. How should these students proceed?

f. Sketch the TLC plate (SiO₂, CH₂Cl₂/hexane (1:2)) with the desired product in lane 1, the starting phenol in lane 2 and the salicylaldehyde (product from step 3) in lane 3. What would change if the solvent mixture used would be CH₂Cl₂/hexane (2:1)?

g. What is used to spot the sample on the TLC plate? What is used to visualize the spots?

2. Most of the students in Chem 30CL have performed several asymmetric syntheses before. One of these reactions was the reduction of camphor with sodium borohydride which afforded a mixture of borneol and isoborneol.

a. What was the product distribution in this reaction?

b. How can this product distribution be rationalized?