Organic Chemistry Peer Tutoring Department CHEM 51B ......Chem 51B Midterm 1 Review KEY 1) Rank the species in each group in order of increasing nucleophilicity. (7.50, 5th) a. CH

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

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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]) 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)


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)



8)


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.



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.



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.



15) Draw the products of each reaction.

a.

b.


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Organic Chemistry Peer Tutoring Department CHEM 51B ......Chem 51B Midterm 1 Review KEY 1) Rank the species in each group in order of increasing nucleophilicity. (7.50, 5th) a. CH