Final Exam Instructions: 1. You must bring a #2 pencil. YOU MAY NOT USE A CALCULATOR 2. Cell phones are not allowed. If you are observed with a cell phone in use or in sight, you will receive a grade of ZERO on the final exam. 3. You may not leave the testing room for any reason. If you must leave the room during the exam, you must turn in your exam first, and you will not be allowed to continue after it is turned in. 4. You will have exactly 110 minutes to complete 70 multiple choice questions. If you are late, you will have less than 110 minutes to complete the exam. 5. Your grade will be determined as a percent of the total points possible. The total number of points possible will be equal to the total number of points earned by whom ever scores the highest on the exam. 6. You will be provided with a test booklet (has abbreviations, periodic table, and some structure on the back side), answer sheet, scratch paper.

Final Exam Instructions: Fill in your: Student # - print number and fill in corresponding bubbles Fill in Name _YOUR NAME LCCC_________________ Subject _First Term Organic Chemistry Period _________ Cell phones are not allowed. If you are observed with a cell phone in use or in sight, you will receive a grade of ZERO on the final exam. You may not leave the testing room for any reason. If you must leave the room during the exam, you must turn in your exam first, and you will not be allowed to continue after it is turned in. You will have exactly 110 minutes to complete 70 multiple choice questions. If you are late, you will have less than 110 minutes to complete the exam. DO NOT DO AROMATIC SECTION!

Final Exam Topics: Some exam questions will relate to topics we never discussed. SAVE THOSE QUESTIONS FOR THE END, and answer them the best you can. Your grade will not reflect your performance on questions that relates to: Fisher Projections Reactions involving the following reagents: NBS, Diels-Alder, free radical reactions UV spectroscopy DO NOT DO AROMATIC SECTION

Topics Solvolysis – substitution reaction where solvent acts as a nucleophile. Usually water is the solvent. naming: alkanes, alkenes, alkyl halides, alcohols, functional groups including ketone, alkene, ether, ester Drawing molecules, formal charge, resonance, sp, sp2 sp3 hybridization, atomic orbital overlap to form molecular orbitals, bond angles, dipole moment Stability: cyclohexanes (axial and equitorial position), 3˚, 2˚, 1˚ carbocations, heat of hydrogenation and stability of alkenes, Newman projections, Physical properties: solubility, boiling point, melting point Lab techniques: distillation, melting point, extractions, recrystallization Reactivity: organic acids and bases, pKa, endothermic vs exothermic, reaction coordinate diagrams, slow (rate determining) step, fast step, nucleophiles (strengths), substitution (SN1 vs SN2 mechanisms), rate laws, leaving groups, eliminations (E1 vs E2 mechanisms), epoxides, ozone reactions, additions (hydration methods, hydrohalogenation, halogenation, halohydrin, hydrogenation methods), epoxide formation, dihydroxylation, use retrosynthesis arrows Isomers: constitutional, stereo (diastereomers, enantiomers), stereocenters, R and S configuration, meso compounds, racemic mixtures, optical rotation, Spectroscopy: IR, MS, 1H NMR and 13C NMR (coupled and decoupled)

Point Distribution For the 2006 ACS exam, the exam grades will be “curved” based on the national norms as follows. Out of 60 total questions graded score points 60 150 46 141 32 80 18 45 59 139 31 78 17 43 58 44 135 30 75 16 40 57 132 29 73 15 38 56 42 129 28 70 14 35 55 41 136 27 68 13 33 54 122 26 65 12 53 149 39 117 25 63 11 52 110 24 10 51 148 37 105 23 9 50 147 36 101 22 8 20 49 146 95 21 7 48 144 34 90 6 47 143 84 19 5

Point Distribution For the 2010 ACS exam, the exam grades will be “curved” based on the national norms as follows. Out of 63 total questions graded score points 63 150 49 131 35 83 21 50 62 48 129 34 81 20 61 47 126 33 79 19 45 60 46 125 32 76 18 43 59 149 120 31 74 17 40 58 44 117 30 71 16 38 57 147 113 29 69 15 36 56 146 42 110 28 66 14 55 144 41 105 27 64 13 54 143 98 26 12 53 141 39 95 25 11 52 140 90 24 10 51 137 37 88 23 9 135 86 22 8

What is the IUPAC name for the compound:

Show all formal charges in the molecule:

Give the hybridization and bond angles at both of the charged carbons in the following molecule.

In the highest energy conformation of trans-1,4-dimethylcyclohexane, how many of the axial positions are occupied by hydrogen atoms?

Draw an energy coordinate diagram that represents a 3 step exothermic reaction in which the second step is the rate determining step.

Rank the following compounds in order of increasing boiling point.

The melting point of solid compound is listed in a textbook to be 213 C. If it is measured in the lab to be 190 – 202 C, what is the most likely explanation?

Which of the following will undergo substitution most quickly?

Rank the following bonds from lowest pKa to highest pKa.

For the following compounds, rank them in order of increasing strength as a nucleophile.

What is the IUPAC name for the compound:

Label all of the stereogenic centers are in the following compound Label all of the stereogenic centers are in the following compound? Is the molecule chiral or achiral?

Give the generic rate law expression for a reaction between a tertiary carbon electrophile and a weak nucleophile.

Give the major product(s) of the following reaction Give the major product(s) of the following reaction. Be careful of stereochemistry.

If the following compound were to react with a solvent in a substitution reaction (solvolysis), show the final product, and draw a reasonable reaction coordinate diagram.

Give a set of reagents that can be used to open the following epoxide from the more hindered site

Label each of the following electrophiles as most likely to undergo SN1, SN2, or no substitution.

Draw a picture that shows two atomic orbitals overlapping to give a sigma ANTIbonding molecular orbital.

Which of the following compounds would most likely result in an elimination reaction rather than a nucleophilic substitution?

Draw the product(s) that would result from ozonolysis of the following molecule.

Give the major product(s) of the following reaction.

Elimination reaction can only occur in an antiperiplanar arrangement Elimination reaction can only occur in an antiperiplanar arrangement. Draw a molecule that is ready to undergo elimination illustrating what is meant by antiperiplanar.

Show the mechanism that illustrates electron movement in the rate determining step of an acid catalyzed dehydration of tert-butyl alcohol.

Rank the following resonance contributors from most stable to least stable.

Label each mechanistic step below as either a free radical initiation, propagation, or termination.

Give the major product(s) of the following reaction Give the major product(s) of the following reaction. Be careful of stereochemistry.

If the following compound were to be monochlorinated using radical chlorination, how many possible products could result, and which product would be the major product? Be careful of stereochemistry.

Draw a picture that shows two atomic orbitals overlapping to give a sigma bonding molecular orbital.

Label each of the following statements as true for SN1, SN2, both, or neither. The mechanism is favored in polar solvents. The rate is independent of the concentration of the nucleophile The reaction proceeds with racemization Rearragements are sometimes possible Polar protic solvents favor the mechanism The rate depends on the concentration of both the nucleophile and the electrophile The reaction occurs with inversion of stereochemistry The reaction is faster with less stable leaving groups

Which two of the following solvents would be best used in combination for an extraction experiment in lab: water, ethanol, dichloromethane?

Give the major product(s) of the following reactions.

Draw the atomic orbitals and resulting molecular orbital that result from atomic orbital overlap in the ammonia molecule. Label each bond with any appropriate hybrid orbital notation.

To distinguish between the following compounds by IR spectroscopy, which key peaks would you look for?

Which two of the following solvents would be best used in combination for a recrystalization experiment in lab: water, ethanol, dichloromethane?

Is the configuration at the carbon indicated R or S?

Rank the following carbocations in order of increasing energy.

What starting materials must be used to make the following product by a Diels Alder reaction?

Which of the following compounds match the given data?