[PDF] [PDF] Practice Tests Answer Keys, Organic Chemistry 2 - Minnesota State

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[PDF] Practice Tests Answer Keys, Organic Chemistry 2 - Minnesota State

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[PDF] Practice Tests Answer Keys, Organic Chemistry 2 - Minnesota State

Practice Tests Answer Keys, Organic Chemistry 2

Online Organic Chemistry 2, Chem 360, Dr. Craig P. Jasperse, Minnesota State University Moorhead

For full class website, see

Test Page

Test 1 Version 1 3

Test 1 Version 2 9

Test 1 Version 3 15

Test 1 Version 4 21

Test 2 Version 1 27

Test 2 Version 2 35

Test 2 Version 3 43

Test 2 Version 4 51

Test 3 Version 1 61

Test 3 Version 2 67

Test 3 Version 3 75

Test 4 Version 1 81

Test 4 Version 2 87

Test 4 Version 3 93

Final Exam 101

1 2

1 JASPERSE CHEM 360 TEST 1 VERSION 1 Alcohols and Retrosynthesis 1. Give the major product for the following reactions. (3 points each) O

MgBr 1. 2. H 3 O PhOH H 2 CrO 4 OCH 3

O1. PhMgBr (excess)

2. H 3 O OH

1. TsCl, pyridine

2. NEt

3 , heat O O

1. LiAlH

4 2. H 3 O OH H Br

1. Na

2. OH

3. PhCHO

4. H 3 O

1. PBr

3

2. Mg3Te

xt

2 2. Give Names or structures for the following: (9 points) para-ethylphenol 3. For each of the following pairs, circle the one that is higher boiling and put a square around the one with the higher water solubility. (4 points) 4. Which of the following statements is true? (4 points) a. When an ether solution of A and B in a separatory funnel is treated with neutral water, only B remains in the ether layer. b. When an ether solution of A and B in a separatory funnel is treated with neutral water, neither A nor B remains in the ether layer. c. When an ether solution of A and B in a separatory funnel is treated with basic water (NaOH/H2O), both A and B remain in the ether layer. d. When an ether solution of A and B in a separatory funnel is treated with basic water (NaOH/H2O), only B remains in the ether layer. 5. For the following transformation, which of the following statements is true? (4 points) a. D is the only acceptable solvent b. C is the only acceptable solvent c. C and D are both acceptable solvents d. B, C, and D are all acceptable solvents e. A and B are the only acceptable solvents OH

Cl OH OHOH a. OHH 3 C OHHO b. OHOH BA Br OH O O D C BA H 2

O CH

3 OH

Solvent Options

1. Mg, solvent

2. H 2 C=O 3. H 3 O +4Te

3 6. Suggest a possible structure for an unknown A whose formula is C5H10O and gives the following chemical test results. (5 points) Formula C5H10O Hydrogenation Test H2/Pt No reaction Chromic Acid Test H2CrO4 Turns Green Lucas Test HCl/ZnCl2 Reacts within 5 minutes 7. Provide the mechanisms for the following reactons (3, 5, and 5 points) OOH

1. LiAlH

4 2. H 3 O Cl O Me OH Me ("Me"=methyl=CH 3

1. MeMgBr

2. H 3 O Me Br Me OH Me Me

H-Br5Te

xt

4 8. Provide the reagents necessary to accomplish the following transformations (4 points each) O

O Ph (2-3 steps) O O OCH 3 Br O OCH 3 (2-3 steps) PhBr PhPh Ph OH (2-3 steps) OH OH (2-3 steps) OH O (2 steps) optically active optically active PhOH PhOH O (4-5 steps)6Te xt

5 9. Rank the acidity of the following, from most acidic (1) to least acidic (4). (4 points) 10. Design syntheses of the following. (6 points each). Allowed starting materials (same as practice) include: cyclopentanol any esters ethylene oxide formaldehyde iodomethane any acyclic alcohol or alkene wth ≤4 carbons any "inorganic" agents (things that won't contribute carbons to your skeleton) OH

OH H 2 O O7Te xt 8

1 JASPERSE CHEM 360 TEST 1 VERSION 2 Alcohols and Retrosynthesis 1. Give Names or structures for the following: (9 points) ortho-chlorophenol 2. For each of the following pairs, circle the one that is higher boiling and put a square around the one with the higher water solubility. (4 points) 3. Of the listed four chemicals, circle those which would ionize methanol (convert it to sodium or magnesium methoxide)? (4 points) Na NaNH2 NaOH CH3MgBr 4. If an ether solution of the following three compounds was washed with NaOH/H2O, which (if any) of the compounds would remain in the ether layer? Circle any that would. (3 points) 5. Of the following common solvents , circle those that are unsuitable as solvents for the preparation and reactions of Grignard reagents (assuming you want the Grignard reagent to react with something else). (3 points) OH

OH OHOHquotesdbs_dbs2.pdfusesText_2