Name:_____________________________________

CHEM 3350
Practice – Streochem/SN1,2

1. Designate each of the indicated stereocenters as either R or S in the box below.

A B C D E F G H I J K L M N

O P Q

Note: Now is a good time to start thinking about the chemical reactions we will study. The following
reactions are a few of those reactions. Don’t be alarmed if you don’t fully understand, we will start the
details soon and you can fill in the blanks. However, think about what could be happening in the
reaction schemes below. Using your chemical knowledge, what do you think could be happening with
respect to reactivity and bonding? Consider the charges, both formal and partial; consider polar covalent
bonds and ionic bonds that have a spectator atom. Also, how would you classify the reactions, ie.,
substitutions, addition, eliminations, or some other type? Hint: they are all the same type.
Advice: Flash cards can be a valuable tool moving forward. We will “see” many different types of
chemicals used in organic chemistry. You will want to be able to quickly recognize a particular reaction
when you see it. Consider writing the information given on the front of a flash card and add the missing
starting material, reagent or product on the back of the card. As you go, you can add specifics.

2. Consider the six reactions below. For each one, fill in the missing component (i.e., the reactant,
product or reagents) in each of the boxes. Be sure to consider stereochemistry, where
appropriate.
3. Mechanism. A mechanism is a sequence of bond making and bond breaking steps that account
for the overall changes in bonding between reactants and products. Most reactions proceed by
movement of pairs of electrons. (R)-5-bromo-3-methyl-1-butanol undergoes a reaction in the
presence of base to form the cyclic ether shown below. The reaction occurs in two mechanistic
steps. Draw the two-step mechanism that accounts for the changes of bonding in the boxes
below. Include all lone pairs and formal charges. (Hint – the first step is an acid-base reaction.)

4a. Does the organic reactant in the reaction above rotate plane polarized light?______________

4b. Does the organic product in the reaction above rotate plane polarized light?______________