Description: final study
Total Problems: 22
On the molecule below, mark each stereocenter with an asterisk. (Note: in some textbooks, stereocenters are referred to as stereogenic centers, chirality centers, or asymmetric centers).
Rank the following compounds in order of decreasing reactivity with NaI in acetone. (1 = most reactive)
After a sample of optically pure (S)-2-ethyl-cyclohexanone is dissolved in an aqueous solution for several hours, a significant loss of optical activity is observed. Explain.
Rank the following anions in order of decreasing stability (1 = most stable)
Rank the following anions in order of decreasing stability (1 = most stable)
Rank the following electrophiles in order of decreasing reactivity with NaN3 in DMF. (1 = most reactive)
Rank the following electrophiles in order of decreasing reactivity with NaN3 in DMF. (1 = most reactive)
Rank the following compounds in order of decreasing nucleophilicity. (1 = most nucleophilic)
Rank the following compounds in order of decreasing reactivity with water (solvolysis). (1 = most reactive)
For the reaction below, draw the structures of the carbocation intermediate and the final product.
Using curved arrows, draw the mechanism for the SN2 reaction below.
For each reaction below, determine whether the primary reaction is SN1, SN2, E1, or E2, and then draw the product.
Note: Me = methyl (CH3)
Show two ways to prepare the ether below from a combination of an alcohol and an alkyl halide via the Williamson ether synthesis.
Is one way better than the other? Why?
Indicate the reagents necessary to carry out each transformation.
Assign R or S configuration for each molecule below.
a) is straightforward. I've started you off in b).
Draw the structure of (2R,3S) 2-bromo-3-chlorobutane using wedges and dashes. Also draw a Fischer projection.
Indicate which of the molecules below are chiral (if any).
For a molecule to undergo an E2 reaction, the leaving group and the beta-proton must be in an anti-coplanar conformation (one atom straight up, the other straight down). Based on this, which compound undergoes E2 reaction with KOtBu faster? Why?
Let's work through a chiral resolution. Write out the structure of the indicated compound in each box. Include stereochemistry.
Why is it possible to separate the (R,R) and (R,S) salts?
Indicate the major organic product of the reaction below. Include stereochemistry.