[PDF] Organic Chemistry Practice Problems and Practice Exams





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Practice Sets

Organic Chemistry II

Table of Contents

• Online Organic Chemistry II, Chem 360, • Dr. Craig P. Jasperse, Minnesota State University Moorhead • For full class website, see

• Fall/spring: https://collaborate.mnstate.edu/public/blogs/jasperse/online-organic-chemistry-courses/online-organic-chemistry-ii-360-fall-spring/

• Summer: https://collaborate.mnstate.edu/public/blogs/jasperse/online-organic-chemistry-courses/online-organic-chemistry-ii-360-summer/

• Face: https://collaborate.mnstate.edu/public/blogs/jasperse/on-campus-chemistry-courses/organic-chemistry-ii-360/

Test Page

Test 1 PS#1: Arrow-Pushing/Mechanisms Practice Set 3

Test 1 PS#2: Acid Base Practice Set 7

Test 1 PS#3: Alcohol-related Mechanisms Problems

11 Test 1 PS#4: Alcohol-Related Retrosynthesis Problems 15

Test 2 PS#1: Jasperse NMR Problems

(this will only show the first ten or 42. It will have link to the full 42- problem practice set, which are also included in the class notes. 17

Test 3 PS1: Mechanism Practice (Many) 27

Test 3 PS2: Retrosynthesis + Synthesis Design Practice 35 Test 4 PS1: Acid-Base Practice 1 (Easy, basics) 39 Test 4 PS2: Acid-Base Practice 2 (Harder, more test representative) 43 Test 4 PS3: Mechanisms, Retrosynthesis + Synthesis 45 1 2

1 Chem 360 Name: Jasperse Quiz (mechanisms) Due: Arrow-Pushing Practice, Page 1: • Draw arrows for each of the steps in the following reactions. • I won't require this on tests, but you may find it useful to include all lone-pairs on atoms that react. • I won't require this on tests, but you may find it useful to draw in all hydrogens on atoms that react. (It is not useful to draw in all H's on atoms that don't react.) • Remember that arrows track the movement of electrons, so an arrow should go from the source of electrons and point directly to the atom that accepts them. Br

H H Br E2 OH Br S N 1 E1 NaI I +NaBr S N 2 H H H NaOH HOH NaBr O + Br H 2 O + H H H Br + Br H 2 O HH + H 3 O HH H H O H O H OH 2 O H H + H-Br (Old Test)1. 2. 3. 4. 5. Br Br H 2 O

3Test 1 PS#1: Arrow-Pushing/Mechanisms Practice Set

2 Page 2: Draw the arrow(s) for each of these steps. 1. OH

H OH 2 2. OH 2 + H 2 O 3. H H H +H 2 O + H 3 O 4. Ph Br Ph + Br _ 5. Ph Br Ph + Br _ OH OH _ 6. Ph Ph + Br _ D-Br D 7. Ph + Br _ D +Ph D Br 8. H O CH 3 H O CH 3 H H OH CH 3

9. OCH

3 _ O OCH 3 O _

10. Ph

Ph + Cl _Br-Cl Br +Ph Br Cl

11. HNEt

3 + Br _ H Br H H NEt 3

4Test 1 PS#1: Arrow-Pushing/Mechanisms Practice Set

3 For each of the following reactions , write whet her the mechanism would be radical, cationic, or anionic? 1. HNO

3 NO 2 2. Br O 2 N NaOH OH O 2 N 3. H OCH 3 OH, H H OCH 3 H 3 CO 4. Br 2 , peroxides Br 5. O Br 2 , NaOH O Br 6. H 2 O, H O OH OH

7. peroxides

etc etc

8. OOCH

3 H 3 CO H 2 O, H 9. O LiCH 3 OLi CH 3

5Test 1 PS#1: Arrow-Pushing/Mechanisms Practice Set

4 Some Arrow-Pushing Guidelines 1. Arrows follow electron movement. 2. Some rules for the appearance of arrows • The arrow must begin from the electron source. There are two sources: a. An atom (which must have a lone pair to give) b. A bond pair (an old bond that breaks) • An arrow must always point directly to an atom, because when electrons move, they always go to some new atom. 3. Ignore any Spectator Atoms. Any metal atom is always a "spectator" • When you have a metal spectator atom, realize that the non-metal next to it must have negative charge 4. Draw all H's on any Atom Whose Bonding Changes 5. Draw all lone-pairs on any Atom whose bonding changes 6. KEY ON BOND CHANGES. Any two-electron bond that changes (either made or broken) must have an arrow to illustrate: • where it came from (new bond made) or • an arrow showing where it goes to (old bond broken) 7. Watch for Formal Charges and Changes in Formal Charge • If an atom's charge gets more positive ⇒ it's donating/losing an electron pair ⇒ arrow must emanate from that atom or one of it's associated bonds. There are two "more positive" transactions: • When an anion becomes neutral. In this case, an arrow will emanate from the atom. The atom has donated a lone pair which becomes a bond pair. • When a neutral atom becomes cationic. In this case, the atom will be losing a bond pair, so the arrow should emanate from the bond rather than from the atom. • If an atom's charge gets more negative ⇒ it's accepting an electron pair ⇒ an arrow must point to that atom. Ordinarily the arrow will have started from a bond and will point to the atom. 8. When bonds change, but Formal Charge Doesn't Change, A "Substitution" is Involved • Often an atom gives up an old bond and replaces it with a new bond. This is "substitution". • In this case, there will be an incoming arrow pointing directly at the atom (to illustrate formation of the new bond), and an outgoing arrow emanating from the old bond that breaks 6Test 1 PS#1: Arrow-Pushing/Mechanisms Practice Set

Organic Chemistry Jasperse Acid-Base Practice Problems A. Identify each chemical as either an "acid" or a "base" in the following reactions, and identify "conjugate" relationships. -You should have one acid and one base on each side -You should have two conjugate pairs 1. 2. 3. 4. 5. B. Choose the More Basic for Each of the Following Pairs (Single Variable). You can use stability to decide. 6. NH3 NaNH2 7. NaOH H2O 8. 9. 10. 11. CH3CH2OH + NaOHCH3CH2ONa + H2OCH3CH2NHLi + CH3OHCH3CH2NH2 + CH3OLiCH3CH2CO2H + CH3MgBrCH3CH2CO2MgBr + CH4CH3OH + H3O+H2O + CH3OH2+CH3CH2NH3+ + CH3OHCH3CH2NH2 + CH3OH2+NHONHNaONaPhO

PhO O

NHNaNHNaO7Test 1 PS#2: Acid Base Practice Set

C. Rank the basicity of the following sets: Multiple Variable Problems 12. CH3MgBr CH3NHNa CH3NH2 13. 14. 15. D. Choose the More Acidic for Each of the Following Pairs: Single Variable Problems 16. 17. 18. 19. 20. 21. O

O O OH

NHNaONaOOHONaNHOOOHONH

3 NH 4 OH 2 OH OH NH 2 CH 3

NH2OHOH

OH O NH 2 NH 2

O8Test 1 PS#2: Acid Base Practice Set

E. Rank the acidity of the following sets: Multiple Variable Problems 22. 23. 24. 25. 26. F. Draw arrow to show whether equilibrium favors products or reactants. (Why?) 27. 28. G. For the following acid-base reaction, a. put a box around the weakest base in the reaction b. put a circle around the weakest acid c. draw an arrow to show whether the equilibrium goes to the right or left. (4pt) 29. OH2OOHOOHHFNH2NH3OOHOH2OOHNH2OHOOHNH2NH3ONH2OOHNH2HeOOHOH

2 O + OH + HOH O HO O ONH2OHNH++ONaNH2NHNaOH++9Test 1 PS#2: Acid Base Practice Set

Chem 341 Jasperse Ch. 1 Structure + Intro 12 Acid-Base Chemistry (Section 1.13-18) Acidity/Basicity Table Entry Class Structure Ka Acid Strength Base Base Strength 1 Strong Acids H-Cl, H2SO4 102 2 Hydronium H3O+, ROH+ cationic 100 H2O, HOR neutral 3 Carboxylic Acid 10-5 4 Ammonium Ion (Charged) 10-12 5 Water 10-16 6 Alcohol 10-17 7 Ketones and Aldehydes 10-20 8 Amine (N-H) (iPr)2N-H 10-33 9 Alkane (C-H) 10-50 Quick Checklist of Acid/Base Factors 1. Charge 2. Electronegativity 3. Resonance/Conjugation y When neutral acids are involved, it's best to draw the conjugate anionic bases, and then think from the anion stability side. • The above three factors will be needed this semester. The following three will also become important in Organic II. 4. Hybridization 5. Impact of Electron Donors/Withdrawers 6. Amines/Ammoniums Cl

O S O OHO ROH O RO O R N R HR

Charged, but only

weakly acidic! R N R R

Neutral, but basic!

HOH HO ROH RO O H O (iPr) 2

N Li

RCH 3 RCH

210TTTBase

StabilityT

e x t1. Cations more acidic than neutrals; anions more basic than neutrals

2. Carbanions < nitrogen anions < oxyanione < halides in stability

3. resonance anions more stable than anions without resonanceTest 1 PS#2: Acid Base Practice Set

Organic(Chemistry(2((Jasperse((Test(1,(Alcohol(Chemistry((Draw(Mechanisms(for(the(Following(Reactions((1. (((((2. (((((3. (((((4. (((((5. (((((OOHMgBr1.2. H+MgBr1.2. H+OOHOHMgBr1.2. H+OHMgBr1.2. H+OHOHMgBr1.2. H+OHO11Test 1 PS#3: Alcohol-related Mechanisms Problems

6. ((((((7. (((((8. ((((((9. ((((((10. ((((((((1.2. H+OBrMgHOO1.2. H+OHLiAlH4OOHNaBH4, CH3OHNaBH4, CH3OHOHOMgBr1.2. H+OO(excess)OH12Test 1 PS#3: Alcohol-related Mechanisms Problems

11. ((((((((((12. (((((((((13. (((((((((14. (((((((MgBr1.2. H+OO(excess)OH1.2. H+MgBr(excess)OOOHOH1.2. H+OHOOMgBrOH1.2. H+OOOHLiAlH413Test 1 PS#3: Alcohol-related Mechanisms Problems

15. (((((((16. (((((17. (((((18. ((((((19. (((((20. (((((1.2. H+OCH3OLiAlH4OH1.2. H+LiAlH4OOHOOH1.2. H+LiAlH4HOOHOOOHBrHBrHClOHClOHBrHBr14Test 1 PS#3: Alcohol-related Mechanisms Problems

More

Retrosynthesis

Problems:

One of the students asked if I could generate 1. O 2. OH 3. 4. OH O 5. Br 6. Br 7. O

15Test 1 PS#4: Retrosynthesis Problems

Harder

Ones (more than one

Grignard

reaction required) 8. OH 9.

10. Br

16Test 1 PS#4: Retrosynthesis Problems

Chem 360 Jasperse NMR Practice Problems 1 Jasperse Organic II NMR Problems 1. C3H7Cl Sat Feb 4 18:00:16 2012: Experiment started

28.09
28.47
43.44
ppm 1.0 1.2 1.4 1.6 1.8 2.0 2.2 2.4 2.6 2.8 3.0 3.2 3.4 3.6

Plotname: 1-Chloropropane_PROTON_01_plot03

17Test 2 NMR: Jasperse NMR Problems This practice-set collection includes only the fifirst 10 or 42 practice

NMR problems. For several reasons:

1. The full 42 are already included within the "all notes" collection.

2. Including the fifirst 10 will give you a chance to re-practice those all

on your own. (I'll do all of the fifirst ten within class, too...)

3. 10 pages worth will match the number of pages in the answer key

document; this way the documents will match up in terms of page numbers.

4. To print off the full set of 42 NMR practice problems, use this link:http://web.mnstate.edu/jasperse/Chem360/Classbook%20360/NMR%20Problems.pdf

Chem 360 Jasperse NMR Practice Problems 2 2. C5H10O Sat Feb 4 15:37:38 2012: Experiment started

2.00 3.10 2.10 3.25 ppm 0.8 1.0quotesdbs_dbs6.pdfusesText_12
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