NAME (Print): Chemistry 610A/618A Dr. Brent Iverson 2nd Exam Oct. 29, 2003 SIGNATURE:
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1 NAME (Print): SIGNATURE: hemistry 610A/618A Dr. ent Iverson 2nd Exam ct. 29, 2003 Please Note: This test may be a bit long, but there is a reason. I would like to give you a lot of little questions, so you can find ones you can answer and show me what you know, rather than just a few questions that may be testing the one thing you forgot. I recommend you look the exam over and answer the questions you are sure of first, then go back and try to figure out the rest. Also make sure to look at the point totals on the questions as a guide to help budget your time. I recommend saving questions marked "challenge" until you are finished with all of the other questions. RELAX, TAKE A DEEP BREAT, TINK ABUT SMETING PEAEFUL AND BEGIN. NERVES AND PANI NLY URT YU, JUST ASK A GUY N TE BMB SQUAD, A SUSPENSIN BRIDGE PAINTER R A BALD GUY SAVING IS EAD!
2 Page Points Total (10) (16) (22) (18) (27) (21) (21) (23) (15) (20) (15) (208) T Score
3 Pg 1 (24) 1. (4 pts. each) Draw the structures indicated by each IUPA name. trans-2-methyl-3-hexene (6Z)-2,6-dimethyl-2,6-nonadiene 2. (4 pts) For the structure, give an acceptable IUPA name. 3. (2 pts each) For the following molecule, in the circles write the hybridization state of the indicated atom, and in the box describe the indicated bond in terms of overlap of hybridized orbitals. For example, a correct answer in a box will be of the form: σ ()sp 3 -()1s 2 2
4 Pg 2 (15) 4. (15 pts. total) Rank the following species in terms of the stated property from 1 to 4 (or 3) as described, with intermediate numbers to rank the species of intermediate stability activity. Please make sure you know what we want, as you will get no credit if you get the numbers backwards! Stability of alkene: Place a 1 under the most stable (i.e. least reactive to 2 /Pt) and a 4 under the least stable (i.e. most reactive to 2 /Pt) Stability of carbocations: Place a 1 under the most stable carbocation and a 4 under the least stable carbocation Relative Acidity: Place a 1 under the most acidic molecule and a 4 under the least acidic molecule. N Relative Acidity: Place a 1 under the most acidic molecule and a 3 under the least acidic molecule. F F F F F F F F F
5 Pg 3 (17) 4. (cont.) (8 pts. total) Rank the following species in terms of the stated property from 1 to 4 as described, with intermediate numbers to rank the species of intermediate stability activity. Please make sure you know what we want, as you will get no credit if you get the numbers backwards! Relative Acidity: Place a 1 under the most acidic moleucle and a 4 under the least acidic molecule. F l I Relative Acidity: Place a 1 under the most acidic molecule and a 4 under the least acidic molecule. l 5. (9 pts total) f the molecules shown below, circle the ones that are optically active, that is the ones for which a sample would rotate the plane of plane polarized light. In other words, circle the molecules that are chiral. l l l l 3 F 2 3 F F F 3
6 Pg 4 (19) 6. (3 pts each) Use your understanding of relative acidities to predict the position of equilibrium in the following acid-base reactions. Draw a circle around the side of each equation that predominates at equilibrium. These may seem difficult at first, but remember what you know about acid-base equilibria as well as relative acid strenghts Na Na Na 3 Na 3 2 hallenge! Think about this one!!!! Li 3 2 Li (5 pts each) In no more than two sentences, define the physical basis for the interactions defined by the following terms. yperconjugation The inductive effect
7 Pg 5 (24) 8. (6 pts each) For each set of reagents, draw the important intermediate or transition state that we discussed in lecture in the box provided. You must show all lone pairs and formal charges on the structures you draw!! Next, draw arrows (either normal arrows or single "fishhook" arrows as appropriate) on the starting material to indicate electron flow to generate the intermediate or transition state that you have drawn. Please read these directions again to make sure you know what we want. Note that we are only interested in the first step of the mechanism here, not the whole thing! A. 3 Intermediate B. 3 Intermediate. Intermediate D. For this one used dotted lines ( ) to indicate bonds being made or broken in the structure you draw. 3 B Transition state
8 Pg 6 (20) 9. (5 pts each structure) The following molecules undergo rearrangment. In each case, draw the first carbocation intermediate in the first box, then the rearranged carbocation intermediate in the second. Include all lone pairs and formal charges, but you do not need to draw arrows. A. 3 3 First carbocation intermediate Rearrangement Rearranged carbocation intermediate B. First carbocation intermediate Rearrangement Rearranged carbocation intermediate
9 Signature Pg. 7 (20) 10. (18 pts.) Read these directions carefully. Read these directions carefully. (It was worth repeating) For the reaction shown below, fill in the details of the mechanism. Draw the appropriate chemical structures and draw arrows to show how pairs of electrons are moved to make and break bonds during the reaction of the indicated alkene with 2 in the presence of 2. Draw all non-bonded electrons as dots around the appropriate atoms and include all formal charges. Draw all products of each step and all products of the overall reaction. MAKE SURE T FILL IN TE BLANK AT TE BTTM. STEP Intermediate A STEP 2 Remember to draw arrows on this structure Intermediate A Intermediate B STEP 3 Remember to draw arrows on this structure Intermediate B All Products of overall reaction (2 pts) During the reaction described by the above mechanism, say what happens to the p of the solution
10 Signature Pg. 8 (8) 10 (cont.) (8 pts.) A. For the reaction mechanism you drew on the previous page, circle the energy diagram that best describes your mechanism. Sorry about the lame curves, imagine they are smoother! Potential Energy Potential Energy Reaction oordinate Reaction oordinate Potential Energy Potential Energy Reaction oordinate Reaction oordinate B. Now draw an X through the energy diagram that best describes the reaction of an alkene with l 2 (with no water in the reaction).
11 Pg 9 (11) 11. (3 or 5 pts each) The following reactions all involve chemistry of alkenes. Fill in the box with the product(s) that are missing from the chemical reaction equations. Draw only the predominant regioisomer product or products (i.e. Markovnikov or non-markovnikov products) and please remember that you must draw the structures of all the product stereoisomers using wedges and dashes to indicate stereochemistry. When a racemic mixture is formed, you must write "racemic" under both structures EVEN TUG YU DREW BT STRUTURES. A. B. 3 2 / Ni. 3 l 2
12 Pg 10 (13) 11 (cont.) (3 or 5 pts each) The following reactions all involve chemistry of alkenes. Fill in the box with the product(s) that are missing from the chemical reaction equations. Draw only the predominant regioisomer product or products (i.e. Markovnikov or non-markovnikov products) and please remember that you must draw the structures of all the product stereoisomers using wedges and dashes to indicate stereochemistry. When a racemic mixture is formed, you must write "racemic" under both structures EVEN TUG YU DREW BT STRUTURES. D. 1) 3 2) ( 3 ) 2 S E. 2 / 2 F. 1) s 4 2) NaS 3
13 Pg 11 (11) 11 (cont.) (11 pts total) When making an alcohol from an alkene it may be important (for physical properties of a desired material or for biological activity of a desired drug) to insert the group at a specific carbon with a specific stereochemistry. For instance 3-methyl-1-butene, shown below, can be converted into several types of alcohols depending on what hydration reagent(s) a chemist uses. In the three boxes below write the reagent(s) that will produce the products shown. Some boxes may require two steps. G Racemic 3 3 These are the three possible products methyl-1-butene 3 This is the only product Racemic 3 These are the only products
14 Pg 12 (20) 12. (4 pts each) The following problems are a new format. We turn the tables and give you the product. In the space provided show the starting material required to make that product using the given reagents. A. 2 / 2 S 4 3 B (Racemic Mixture). 1) 3 2) ( 3 ) 2 S D. 1) B 3 2) 2 2 / 2 E. 2 / Pd (Meso)
15 Pg 13 (24) 13. (24 pts.) Take your time on this. Use the back of the previous page for scratch paper if that helps. For the following reactions, draw ALL of the stereoisomers of the constitutional isomers produced (i.e. all the different product molecules). If your answer ends up being a little messy, circle all the final structures you want graded. A. 2 / 2 S 4 B. 1) B 3 2) 2 2 /
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