organic chemistry peer tutoring department chem 51b ......chem 51b midterm 1 review key 1) rank the...

Organic Chemistry Peer Tutoring Department CHEM 51B University of California, Irvine Professor Bess Clever Chiu (cleverc@uci.edu) https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo (jslo1@uci.edu) Jacqueline Nguyen (jacqunn2@uci.edu)

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:cleverc@uci.edumailto:jslo1@uci.edumailto:jacqunn2@uci.edu

Organic Chemistry Peer Tutoring Department CHEM 51B University of California, Irvine Professor Bess Clever Chiu (cleverc@uci.edu) https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo (jslo1@uci.edu) Jacqueline Nguyen (jacqunn2@uci.edu) 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:cleverc@uci.edumailto:jslo1@uci.edumailto:jacqunn2@uci.edu

Organic Chemistry Peer Tutoring Department CHEM 51B University of California, Irvine Professor Bess Clever Chiu (cleverc@uci.edu) https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo (jslo1@uci.edu) Jacqueline Nguyen (jacqunn2@uci.edu) 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 (cleverc@uci.edu) https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo (jslo1@uci.edu) Jacqueline Nguyen (jacqunn2@uci.edu)

8)

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Organic Chemistry Peer Tutoring Department CHEM 51B University of California, Irvine Professor Bess Clever Chiu (cleverc@uci.edu) https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo (jslo1@uci.edu) Jacqueline Nguyen (jacqunn2@uci.edu) 9)

10)

11) Draw a stepwise mechanism for the reaction. Draw all products and label the major product.

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Organic Chemistry Peer Tutoring Department CHEM 51B University of California, Irvine Professor Bess Clever Chiu (cleverc@uci.edu) https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo (jslo1@uci.edu) Jacqueline Nguyen (jacqunn2@uci.edu)

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.

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Organic Chemistry Peer Tutoring Department CHEM 51B University of California, Irvine Professor Bess Clever Chiu (cleverc@uci.edu) https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo (jslo1@uci.edu) Jacqueline Nguyen (jacqunn2@uci.edu)

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:cleverc@uci.edumailto:jslo1@uci.edumailto:jacqunn2@uci.edu

Organic Chemistry Peer Tutoring Department CHEM 51B University of California, Irvine Professor Bess Clever Chiu (cleverc@uci.edu) https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo (jslo1@uci.edu) Jacqueline Nguyen (jacqunn2@uci.edu)

15) Draw the products of each reaction.

a.

b.

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Organic Chemistry Peer Tutoring Department CHEM 51B University of California, Irvine Professor Bess Clever Chiu (cleverc@uci.edu) https://sites.uci.edu/ochemtutors/bess-51b-40460/ Jason Lo (jslo1@uci.edu) Jacqueline Nguyen (jacqunn2@uci.edu)