-
Organic Chemistry Peer Tutoring Department CHEM 51B University
of California, Irvine Professor Bess Clever Chiu ([email protected])
https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo
([email protected]) Jacqueline Nguyen ([email protected])
Chem 51B Midterm 1 Review KEY 1) Rank the species in each group
in order of increasing nucleophilicity. (7.50, 5th)
a. CH3CH2S—, CH3CH2O—, CH3CO2— in CH3OH
b. CH3NH2, CH3SH, CH3OH in acetone
2) For each reaction, determine if the mechanism is E2, E1, SN2,
or SN1. (7.34, 5th)
SN1
SN2
mailto:[email protected]:[email protected]:[email protected]
-
Organic Chemistry Peer Tutoring Department CHEM 51B University
of California, Irvine Professor Bess Clever Chiu ([email protected])
https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo
([email protected]) Jacqueline Nguyen ([email protected]) 3)
Diphenhydramine, the antihistamine in Benadryl, can be prepared by
the following two-step sequence. What is the structure of
diphenhydramine? Only draw the products in the box. (7.66, 5th)
4) In the box below, draw the major product for the following
reaction. (8.54, 5th)
mailto:[email protected]:[email protected]:[email protected]
-
Organic Chemistry Peer Tutoring Department CHEM 51B University
of California, Irvine Professor Bess Clever Chiu ([email protected])
https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo
([email protected]) Jacqueline Nguyen ([email protected]) 5) Fill in the
box with the correct reagent needed to obtain the products below.
(8.63, 5th)
CH3OH
6)
7)
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-
Organic Chemistry Peer Tutoring Department CHEM 51B University
of California, Irvine Professor Bess Clever Chiu ([email protected])
https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo
([email protected]) Jacqueline Nguyen ([email protected])
8)
mailto:[email protected]:[email protected]:[email protected]
-
Organic Chemistry Peer Tutoring Department CHEM 51B University
of California, Irvine Professor Bess Clever Chiu ([email protected])
https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo
([email protected]) Jacqueline Nguyen ([email protected]) 9)
10)
11) Draw a stepwise mechanism for the reaction. Draw all
products and label the major product.
mailto:[email protected]:[email protected]:[email protected]
-
Organic Chemistry Peer Tutoring Department CHEM 51B University
of California, Irvine Professor Bess Clever Chiu ([email protected])
https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo
([email protected]) Jacqueline Nguyen ([email protected])
The first product is the major product because it is a
tri-substituted alkene. 12) Draw the products of each reaction and
indicate stereochemistry around stereogenic centers.
a.
mailto:[email protected]:[email protected]:[email protected]
-
Organic Chemistry Peer Tutoring Department CHEM 51B University
of California, Irvine Professor Bess Clever Chiu ([email protected])
https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo
([email protected]) Jacqueline Nguyen ([email protected])
b.
13) Draw two different routes for the following ether using a
Williamson ether synthesis. Indicate the preferred route.
14) Draw the products and a stepwise mechanism for the
reaction.
mailto:[email protected]:[email protected]:[email protected]
-
Organic Chemistry Peer Tutoring Department CHEM 51B University
of California, Irvine Professor Bess Clever Chiu ([email protected])
https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo
([email protected]) Jacqueline Nguyen ([email protected])
15) Draw the products of each reaction.
a.
b.
mailto:[email protected]:[email protected]:[email protected]
-
Organic Chemistry Peer Tutoring Department CHEM 51B University
of California, Irvine Professor Bess Clever Chiu ([email protected])
https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo
([email protected]) Jacqueline Nguyen ([email protected])
mailto:[email protected]:[email protected]:[email protected]
