Organic Chemistry I: Biological Emphasis - Test 2/Unit 2 Study Guide and Key
Organic Chemistry I: Biological Emphasis - Test 2/Unit 2 Study Guide and Key CHEM 3053-160
Popular in Organic Chemistry: Biological Emphasis I
verified elite notetaker
Popular in Chemistry
This 22 page Study Guide was uploaded by Elizabeth McKitrick on Tuesday June 7, 2016. The Study Guide belongs to CHEM 3053-160 at University of Oklahoma taught by Mr. J Garrett in Spring 2016. Since its upload, it has received 72 views. For similar materials see Organic Chemistry: Biological Emphasis I in Chemistry at University of Oklahoma.
Reviews for Organic Chemistry I: Biological Emphasis - Test 2/Unit 2 Study Guide and Key
Report this Material
What is Karma?
Karma is the currency of StudySoup.
You can buy or earn more Karma at anytime and redeem it for class notes, study guides, flashcards, and more!
Date Created: 06/07/16
Organic Chemistry I: Biological Emphasis Unit 2 Test Study Guide Chapter 5 1.) What kind of isomers have different structures, but the same chemical formula? 2.) What kind of isomers have the same formula and the same connectivity, but different spacial arrangement? 3.) Which kind of stereoisomer has identical R-groups on the same side of the bond? 4.) Which kind of stereoisomer has identical R-groups on the opposite side of the bond? 5.) What kind of stereochemistry has no identical R-groups? 6.) What is this called? (A carbon that has 4 different R-groups) 7.) What kind of stereochemistry has two identical R-groups on the same carbon? 8.) If two molecules form mirror images of each other, but they are not superimposable, what are they called? 9.) If two molecules form mirror images of each other, and they are superimposable (they are essentially the same compound), what are they called? 10.) If two molecules do not form mirror images of each other, what are they called? 11.) In the Cahn-Ingold Prelog System… a.) Does the atom with the highest atomic number hold the lowest or highest priority? b.) What about the atom with the lowest priority? c.) Should the lowest priority group be placed in the front or the back? d.) If the groups’ priority is clockwise, is this the S or R configuration? e.) What about counterclockwise? 12.) How is a tie broken when using the Cahn-Ingold Prelog System? 13.) What is the formula that can be used to determine the number of stereoisomers for a particular molecule? (Define all parts) 14.) Can a compound with only one chiral center ever have an achiral isomer? (If so, what is it called?) 15.) Can a compound with more than one chiral center ever have an achiral isomer? (If so, what is it called?) Chapter 6 1.) What is the energy required to make or break a bond? (And its abbreviation) 2.) What is the term used to describe the energy of a system? (And its symbol) 3.) What is the formula for the change in energy in a reaction? (Define all parts) 4.) Exothermic vs. Endothermic a.) Which reaction gives out energy, and which takes energy in? b.) In which reaction is H negative, and in which is H positive? c.) In which reaction are the products more stable, and in which are the reactants more stable? d.) In which reaction are products favored at equilibrium, and in which are reactants favored at equilibrium? 5.) Are exothermic reactions always spontaneous? 6.) What is the term used to describe the disorder of a system? (And its symbol) 7.) Rank each state of matter according to its level of entropy from high to low: solid, liquid, and gas. 8.) Will S be positive or negative in a reaction where there are more moles of reactant than product? 9.) What describes whether or not a reaction will be spontaneous? (And what is its symbol) 10.) What is the formula that can be used to determine whether a reaction is or is not spontaneous? (Define all parts) 11.) Is G positive or negative for a spontaneous reaction and what is this called? 12.) Is G positive or negative for a nonspontaneous reaction and what is this called? 13.) Does spontaneity describe the speed of the reaction? If not, what does it describe? 14.) What formula can be used to find an equilibrium constant (k ) for eq a particular reaction? 15.) a.) What formula relates G to k ? eq b.) If eqis greater than or equal to 1, which side of the reaction is favored? c.) If eqis less than 1, which side of the reaction is favored? d.) If eqis greater than or equal to 1, is the reaction spontaneous or nonspontaneous? 16.) Does kinetics describe the speed of the reaction? If not, what does it describe? 17.) What is the equation for the rate of a reaction? (Define all parts) 18.) a.) How many reactants affect the rate of a first order reaction? (Draw an example) b.) What about a second order reaction? (Draw 2 examples) c.) What about a third order reaction? (Draw 3 examples) 19.) How would the overall order of a particular reaction be determined? 20.) How is rate (and order) of a reaction determined? 21.) Name 4 factors that can affect the rate of a reaction. (And how they will affect the rate). 22.) What are the “humps” (energy maximums) and “valleys” (energy minimums) in a reaction coordinate diagram? 23.) Which one occurs when bonds are being simultaneously made and broken? 24.) Which one occurs when there are no bonds being made or broken? 25.) Electrophiles vs. Nucleophiles a.) Which one is electron rich and which one is electron poor? b.) Which one is more likely to have a negative charge and which one is more likely to have a positive charge? c.) Which one would donate an electron pair and which one would accept an electron pair? d.) Which one is a Lewis acid and which one is a Lewis base? e.) Which one does electrons flow to and which one does electrons flow from? f.) Which one would be made from a carbocation and which one would be made from a carbanion? 26.) What are the 4 ways electrons move in an ionic reaction? 27.) Which halides make good and which halides make bad leading groups? 28.) What is it called when a compound stabilizes itself through slight interaction/overlap between the electrons in a sigma bond and an empty antibonding orbital? 29.) Draw examples of the following carbocations: methyl, primary, secondary, and tertiary 30.) Which form of the carbocation is the most stable and which is the least stable? Chapter 7 1.) What type of reaction involves the exchange of one functional group for another? 2.) What 2 factors make for a good leading group? 3.) What functional group is most commonly used in substitution reactions? 4.) What suffix ending is used when naming a halide substituent group? 5.) What 5 steps should be taken when naming a chain that contains a halide? 6.) What is the common name for Dichloromethane? (DCM) 7.) What is the common name for the most simple alkene? 8.) Draw examples of the following alkyl halides: primary, secondary, and tertiary 9.) Draw a general SN1 reaction using a secondary alkyl halide. 10.) Draw a general SN2 reaction using a secondary alkyl halide. 11.) When the carbons on an alkyl halide are numbered using Greek letters, where does the substitution occur? 12.) SN1 vs. SN2 a.) Which one is a concerted process (simultaneous, one step), and which one is a stepwise process (more than one step)? b.) What do the S, N, 2, and 1 stand for? c.) Define unimolecular and bimolecular. d.) Draw the rate equation for both SN1 and SN2 reactions. e.) Rank the following molecules according to how well the react from least to greatest in SN1 reactions and in SN2 reactions: methyl, primary, secondary, and tertiary. f.) What order are SN1 reactions? What about SN2? g.) Will SN1 reactions form more S or R stereoisomers? What is this called? Does SN2 have a stereoisomer preference? h.) How many transition states and how many intermediates do each, SN1 and SN2, have? 13.) If an SN1 reaction contains an acid or a base, what other “step” will occur and when in the reaction will this happen? 14.) Can this happen in an SN2 reaction? 15.) What is it called when a solvent is also used as a nucleophile? 16.) If a halide is used in an SN2 reaction, will propanation happen at - the beginning or end of the reaction? What about if OH is used? 17.) What 4 factors play a role in determining whether SN1 or SN2 will take place? 18.) Will the following substrates usually cause an SN1 reaction, SN2 reaction, either, or neither? (Draw an example of each) 1-general methyl 2-general first degree 3-general second degree 4-general third degree 5-first degree allylic halide 6-first degree benzylic halide 7-sp 2 hybrids 19.) Do better leading groups generally cause SN1 or SN2 reactions? What about bad leading groups? 20.) Are good leading groups the conjugate bases of strong or weak acids? 21.) Draw 7 examples of good leading groups. 21.) Are bad leading groups the conjugate bases of strong or weak acids? 22.) Draw 2 examples of bad leading groups. 23.) Do strong or weak nucleophiles generally cause SN1 reactions? What about SN2 reactions? 24.) Name 10 common strong nucleophiles and 3 common weak ones. 25.) What is it called when an atom has an extra hydrogen connected to an electronegative atom? 26.) What is it called when there in not an extra hydrogen connected to an electronegative atom? 27.) Does polar protic favor SN1 or SN2 reactions? What about polar aprotic? Why? 28.) Draw 5 examples of polar protic compounds and 5 examples of polar aprotic compounds. 29.) Complete the following table: R – Leading Group + what? Produces what? Which is a(n)… Ester Nitrate Thiol Alcohol Ether Alkyl Halide Chapter 8 1.) What type of functional group is normally formed by an elimination reaction? Which carbon (using the Greek alphabet) does this occur on? 2.) What suffix ending is used to name alkene parent chains and substituents? 3.) When numbering a parent chain, if there is a tie between an alkene and another R group, such as a methyl group, in having the lowest number, which one should be lower? 4.) Draw examples of the following common compounds and substituents: 1-ethylene 2-propylene 3-styrene 4-vinyl 5-allyl 6-phenyl 7-methylene 5.) Do small cyclic alkenes form cis-isomers, trans-isomers, or both? 6.) With alkenes, what is another way to label a cis isomer? What about the trans isomers? 7.) Which conformation is more stable? Less stable? Has more steric strain? Less steric strain? 8.) Draw and rank each of the following ( -substituted) from least reactive/most stable to most reactive/least stable. Mono-, Di-, Tri-, and Tetra- 9.) What is the most common isomer produced by a reaction called? What about the rest of the isomers produced by the same reaction? 10.) E1 vs. E2 a.) What do E, 1, and 2 stand for? b.) Write the rate equations for both E1 and E2 reactions. c.) What order is an E1 reaction? What about an E2 reaction? d.) Which one is a concerted and which one is a stepwise reaction? e.) In an E2 reaction, rank the following from least to most st reactive: 1 degree alkyl halide, 2 nddegree alkyl halide, and 3 degree alkyl halide Do the same for an E1 reaction. Draw examples of each. f.) Draw a basic E1 and a basic E2 reaction. 11.) Draw examples of the Zuitsav and Hoffman isomers. Which one has a more stable double bond? Which one has a less stable double bond? Which one is the major product for elimination reactions involving “bulky” bases? Which one is the major product for elimination reactions involving “lighter” bases? 12.) For an E2 reaction, will E or Z isomers be more commonly produced? 13.) What about for an E1 reaction? Will it prefer Zuitsav or Hoffman isomers? 14.) Do proton transfers happen in elimination reactions? If so, when and why? 15.) Nucleophile vs. Base a.) Which one “attacks” electrophiles? + b.) Which one depropanates compounds (steals an H )? c.) Which is and which is not very polarizable? d.) Which one tends to have a lone pair on a larger atom? Which one tends to have a lone pair on a smaller atom? 16.) & 17.) Complete the following tables. Common Common Common Nucleophiles Common Bases (2) Strong Nucleophiles Weak Nucleophiles (7) ONLY (4) (3) ONLY and Strong Bases and Weak Bases What is reacting? With what? SN1, SN2, E1, or E2? 1° Nucleophile ONLY 2° 3° Base ONLY 1° 2° (small base) 3° 1° Base ONLY (“bulky” base) 2° 3° 1° Strong Nucleophile 2° and Strong Base 3° Weak Nucleophile 1° and Weak Base 2° 3°
Are you sure you want to buy this material for
You're already Subscribed!
Looks like you've already subscribed to StudySoup, you won't need to purchase another subscription to get this material. To access this material simply click 'View Full Document'