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O-Chem I Final Exam Study Guide

by: Shea Claflin

O-Chem I Final Exam Study Guide CHEM 2451

Marketplace > University of Denver > Chemistry > CHEM 2451 > O Chem I Final Exam Study Guide
Shea Claflin
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About this Document

This study guide is a compilation of questions from the exam 1 and 2 study guides, as well as covering material between the exams, and after the second exam.
Organic Chemistry I
Dr. Peter J. Harrington
Study Guide
50 ?




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This 14 page Study Guide was uploaded by Shea Claflin on Monday March 7, 2016. The Study Guide belongs to CHEM 2451 at University of Denver taught by Dr. Peter J. Harrington in Fall 2016. Since its upload, it has received 66 views. For similar materials see Organic Chemistry I in Chemistry at University of Denver.


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Date Created: 03/07/16
Organic Chemistry Harrington Study Guide Final Exam – Test Date March 12 th 1) Explain the following concepts about atomic orbitals a) Aufbau Principle b) Pauli Exclusion Principle c) Hund’s Rule d) What orbitals correspond to each energy level/shell? e) Be sure to know how to write electron configurations 2) What is electronegativity? What is its range? 3) What is the difference between ionic, polar covalent, and covalent bonds? What is the Δ in electronegativity for each bond? ΔEN is represented by δ + or – in structures 5) Know how to draw a resonance structure. Practice by drawing the resonance structure for CO 2Review Guidelines) 6) What direction to arrows point in curved arrow notation? 7) Know how to draw hybrid orbital diagrams. Draw one for NH 3 8) What is the general trend for atomic size in the periodic table? How does this affect bond length? 9) Explain the differences between Molecular Orbital theory and Valence Bond theory. 10) What is the general formula for alkanes? 11) What is the root name of alkanes with: 1 Carbon: 2 Carbons: 3 Carbons: 4 Carbons: 5 Carbons: 6 Carbons: 7 Carbons: 8 Carbons: 9 Carbons: 10 Carbons: 12) What are constitutional isomers? What are the constitutional isomers for propane and butane? 13) What are the IUPAC System’s steps for naming alkanes? 1. 2. 3. 4. 5. 6. 7. (don’t forget sub-steps) 15) Describe the process for naming cycloalkanes. How do you number the carbons? How do you know if the molecule is named as an alkane or a cycloalkane? 16) What saturates alkanes? Are cycloalkanes saturated or unsaturated? 17) Degree of unsaturation = ? 18) How do you classify carbons in an alkane or cycloalkane? What is the degree of the hydrogen? 19) Describe the difference between intermolecular forces and intramolecular forces. 20) What happens when a solid melts or a liquid boils? What happens to the entropy? 21) Describe the three types of intramolecular attractive forces. Rank them strongest to weakest. Review how they help to predict boiling, melting point, and solubility. 1. 2. 3. 22) How do you use Newman Projections to illustrate the rotation of C-C bonds? 23) What angles are gauche and anti forms found at? What angles are staggered? What angles are eclipsed? Which of those positions is higher in energy? 24) Explain torsional and steric strain. 25) What are Lewis Acids and Lewis Bases? 26) What are Bronsted Acids and Bronsted Bases? 27) K eq = [ ] [ ] [ ] [ ] And K eq = [ ] [ ] at equilibrium [ ] 28) What are conjugate bases and conjugate acids? 29) How do you find pK ? Waat constitutes a weak or strong acid? 30) In curved arrow notation, how many are present in proton transfer reactions? Substitution reactions? Why? 31) Describe the process for comparing the acidity of two substances. (the three steps) 32) What are the rules of solubility? 33) What is the difference between the energies of the reagents and the products of a reaction? 34) What is a transition state? 35) What are the two types of bonds that form a C=C bond? Which one is stronger? 36) What constitutes an alkene? What is an alkene’s general formula? What kind of bonds make up the double bond? 37) What are stereoisomers and why are they present in alkenes? 38) Alkene nomenclature: 1. What are the different suffix’s for number of C=C bonds? 2. How do you order the C’s in the carbon chain? What component gets the lowest #? 3. Where does the C # for the C=C bond get placed in the final name? 4. Draw out the following Alkenyl Substituents: Vinyl Allyl Isopropenyl 39) Describe the difference between cis and trans prefixes. With what alkenes can these be used? Where is the axis of symmetry drawn on the molecule? 40) How do you determine which substituent group has higher priority in cis/trans nomenclature? What if the first two atoms encountered have the same priority? 41) What is the difference between E and Z prefixes? With which types of alkenes is this nomenclature used? Where is the axis of symmetry drawn on the molecule? 42) Describe the process for determining the priority of substituent groups for E/Z nomenclature. What happens if you encounter equal priorities? 43) How do you determine the root name for cycloalkenes? Where do you begin numbering the C’s in the carbon chain? 44) What are the four “first principles” for determining acidity? 45) Describe the process of the hybridization effect: Step 1) Step 2) Step 3) 46) Remember how to determine degrees of unsaturation. Are alkenes saturated or not? 47) Why are C-C bonds polar when one C has a C=C bond? How do you determine molecule polarity? 48) What determines if a reaction is endothermic or exothermic? Be sure to know how to compare ΔH° in reaction to determine which product is favorable. 49) How do bond dissociation energies affect the outcome of a reaction? 50) What does it mean if a C in an alkene is monosubstituted? Disubstituted? Trisubstituted? Tetrasubstituted? What are the relative stabilities of these in the case of constitutional isomers? 51) Referring to reaction #1, how is this hydrogenation reaction a way to obtain stability data of the isomers of butene? 52) What is Markovnikov’s Rule? How does this relate to regioselectivity? 53) How are carbocations formed? What makes a major product of a carbocation reaction more stable than a minor product? 54) What is the significance of activation energy, energy of reactants, and energy of products in an energy diagram of a reaction coordinate? 55) How does Markovnikov’s Rule extend to the addition of H-OH? 56) Know the steps of a hydration reaction mechanism. Be able to draw the arrows for electron transfers. 57) What is Le Chatalier’s Principle? 58) How does a 2° carbocation rearrange to form a 3° carbocation? Why? 59) What is the difference between a curved arrow with a full arrow and a curved fishhook arrow? 60) Describe the following: Initiation steps: Propagation steps: Termination steps: 61) What does the hyperconjugation of pyramidal geometry and trigonal planar geometry when the middle C only has one electron in its sp orbital? 62) How do you use bond association energies to predict what atoms will bond during a reaction? 63) How does the direction of approach during a reaction with a cycloalkane affect the different products? 64) What reaction mechanism involves the partial opening of bonds that results in sharing of a positive charge? 65) Why is mercury used in reaction #8 when the same reaction can be carried out with water and an acid? 66) Know the mechanisms for reactions 1-9. 67) List of alkene concepts to know: Mechanisms regioselectivity/stereoselectivity Multiple steps or concerted Energy diagrams intermediates/transition states Carbocations Radicals Kinetics Fast/Slow Proton transfers LA-LB transfers 68) What are enantiomers? 69) What is the difference between chiral and achiral? 70) Fill in the flow chart for relationship between two molecules: Do they have the same formula? No, they are ___________________ Yes, they are______________________… Do they have the same connectivity? No, they are ___________________________ Yes, they are__________________________... Are they mirror images? No, they are________________________ Yes, they are________________________ 71) What are the steps for the R,S nomenclature system (Cahn-Ingold- Prelog)? Step 1) Step 2) Step 3) Step 4) Step 5) Step 6) 72) How is a polarimeter used to distinguish between enantiomers? 73) What is a racemic mixture? 74) Describe the following cyclohexane conformations: a) banana bond b) butterfly c) boat d) chair 75) Practice turning a planar cyclohexane ring into a chair confirmation drawing. Draw both possible chairs for the molecule. 76) Review the rules of symmetry for cyclohexanes when looking at a planar ring drawing: 77) What is the process for ether and thioether nomenclature? 78) What is the process for alcohol and thiol nomenclature? 79) What is the process for alkyl halide nomenclature?


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