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(CHEM245) Exam 1: Study Guide

by: Brie

(CHEM245) Exam 1: Study Guide CHEM 245

Marketplace > Colorado State University > Chemistry > CHEM 245 > CHEM245 Exam 1 Study Guide

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About this Document

This study guide covers chapters 1-3 for Fundamentals of Organic Chemistry (Text: Essential Organic Chemistry, 3rd edition, by Paula Bruice). Thorough explanations, diagrams, and examples provided....
Fundamentals of Organic Chemistry
Patricia K Somers
Study Guide
Organic Chemistry, fundamentalsoforganicchemistry, chem245, Chemistry, Studyguide, exam1
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This 14 page Study Guide was uploaded by Brie on Sunday September 11, 2016. The Study Guide belongs to CHEM 245 at Colorado State University taught by Patricia K Somers in Fall 2016. Since its upload, it has received 206 views. For similar materials see Fundamentals of Organic Chemistry in Chemistry at Colorado State University.


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Date Created: 09/11/16
Sunday, September 11, 2016 Organic Chemistry (CHEM245): Exam 1 Study Guide Chapter 1 1. Know how to draw a lewis structure from a molecular formula • Ex) C₂H₆O • Don’t forget formal charges • Formal Charge: (# of valence electrons) - (lone pair electrons + # of bonds) A. Try drawing BCl ₃ and NH ₄⁺ (Answers on answer sheet below) 2. Draw or interpret condensed structures B. How would you write C₃H₈O as a condensed structure? (Answer on answer sheet below) • It’s helpful to draw the lewis structure and determine the groups attached • Hint: There seems to be 2 CH₃ groups which would translate to be (CH₃)₂ Now find the rest of the condensed structure 3. Know how to label with sp, sp², sp³ • Sp: Carbon has one triple bond or two double bonds Sp²: Carbon has one double bond • • Sp³: Carbon has single bonds 4. Be able to describe the geometry and bond angle and describe types and numbers of orbitals on hybridized atoms • The number of electron domains determines the number of hybrid orbitals Hybridization # atoms C is bonded 4 3 2 to: Hybridization of C: sp³ sp² sp Bond Angles: 109.5° 120° 180° Molecular Geometry: Tetrahedral Trigonal Planar Linear 1 Sunday, September 11, 2016 5. Know about bonding in terms of overlapping Sp Sp² Sp³ 6. Bond Polarity based on electronegativity values • How to determine type of bond formed • Formula: (Larger electronegativity value - smaller electronegativity value) • Bond Polarity: Describes the sharing of electrons and depends on the electronegativity difference - The greater difference in electronegativity means more polarity - If electronegativities are equal then the bond is non-polar covalent - If the difference in electronegativities is greater than 0 but less than 2 then the bond is polar covalent - If the difference in electronegativities is 2.0 or greater then the bond is ionic 2 Sunday, September 11, 2016 7. Electronegativity Values • Electronegativity increases from left to right across a row • Electronegativity increases from bottom to top within a column Chapter 2 1. Know how to Identify acids and bases • Acid: Loses a proton (H) • pH: Indicates the concentration of protons in a solution o pH = -log[H+] o Lower the pH number = more acidity •The acid will have the lower pKa (stronger acid = lower pKa) Strong Acids: • oHC o H2SO4 oIH o HBr oH • Base: Gains a proton (H) • OH- • CO₃²- • HCO₃- 2. Know how to draw conjugate acids and bases • When an acid loses a proton (H), the conjugate base is formed •Stronger the acid, weaker the conjugate base • When a base gains a proton (H), the conjugate acid is formed 3. Know how to determine pKa • pKa = -logKa 4. Know how to determine relative acidity based on pKa • The larger the Ka, the stronger the acid • The smaller the pKa, the stronger the acid 3 Sunday, September 11, 2016 o pKa < 1 Very strong acid o pKa = 1-3 Moderately strong acid o pKa = 3-5 Weak acids o pKa = 5-15 Very weak acids o pKa > 15 Extremely weak acid 5. Know how to determine if an acid will be protonated with a given pH based on pKa (know how to draw acidic or basic form at that pH) 6. Identify the acid in a reaction 1. Count the # of hydrogens on each substance before and after 2. If the # of hydrogens has decreased, that substance is the acid OR 3. If the # of hydrogens has increased then that substance is the base 7. Equilibria of acid-base reactions 8. Identifying the three most common acid-base organic functional groups (know how to draw the acidic or basic form) • Alkanes: Hydrogen and carbon atoms (saturated hydrocarbons) arranged in a tree-like structure (all carbon bonds are single) o Methane o Ethane o Propane • Alkenes: Unsaturated hydrocarbons that contains a double bond o Ethylene o Propylene • Alkynes: Unsaturated hydrocarbons that contain a triple bond • Sp (most electronegative) > Sp3 (least electronegative) • More bonds = stronger acid (triple > double > single) 9. Relative acidity and basicity based on the structure • Electronegativity • Greater the electronegativity, greater the stability • C < N < O < F • Size • More important than electronegativity • Stability of anion increases down the periodic row • HI >HBr > HCl > HF 4 Sunday, September 11, 2016 • Hybridization • Sp (most electronegative) > Sp3 (least electronegative) • More bonds = stronger acid (triple > double > single) • Closeness to Functional Groups • Close proximity to a functional group can determine if the substance is more acidic etc. • Resonance • Rules of Writing Resonance: 1. Full Valence Electrons: All atoms must have complete octets (H is an exception) 2. Structures that have greater covalent bonds contribute more than structures with less covalent bonds 3. Structures that have a charge separation contribute less 4. 4. Structures that have a (-) charge on a more electronegative atom will be favored in comparison to structures that have a (-) charge on the less electronegative atom. Chapter 3 1. Know how to name cycloalkanes and alkanes through the IUPAC system from structure given 1. Find Parent Chain • Find the parent chain by identifying the longest, continuous carbon chain • ^^^This will be the parent chain • Note: If multiple carbon chains are the same length, choose the chain path that has more branches (Which is evident in image #1- The two branches are (CH₃) and (CH₂— CH₃)). 5 Sunday, September 11, 2016 2. Number the Carbons • Number the carbon atoms so that the branch points have the lowest possible numbers available • Ex) Image #1 would be the most desirable • If there’s branching that is equal from both ends, then count so the second branch will have the lowest number • Ex) #1 would be the correct choice 6 Sunday, September 11, 2016 3. Substituents • Identify and number the substituents; then list them in alphabetical order • If you see 2 substituents on the same carbon then assign them the same number 4. Writing Out the Name • Hyphens (-): Separates prefixes • Commas(,): Separates numbers • Substituents should be listed in alphabetical order • If multiple identical substituents are present then use prefixes - Di: For two - Tri: For three - Tetra: For four ***Di, Tri, and Tetra are not used when putting in alphabetical order*** 7 Sunday, September 11, 2016 • Final: 3-ethyl-4,7-dimethylnonane 2. Know how to draw structures from an IUPAC name 1. Look for the substituent (In this case pent- which means 5 carbons) 2. See which number the branch is on (which carbon is it (the branch) bonded to? when properly counting, what is that carbon’s number?) • Ex) 2-Methylpentane • There are 5 carbons in the chain (longest chain) • The “2” in 2-Methylpentane indicates the branch is on the second carbon 3. Cis/ Trans for cycloalkanes 4. Know names of parent carbon chains and substituents (C1-C10) 1. C1: Meth (methane) 2. C2: Eth (ethane) 3. C3: Prop (propane) 4. C4: But (butane) 5. C5: Pent (pentane) 8 Sunday, September 11, 2016 6. C6: Hex (hexane) 7. C7: Hept (heptane) 8. C8: Oct (octane) 9. C9: Non (nonane) 10. C10: Dec (decane) • Common Names for alkyl substituents: • CH ₃ — Methyl • CH CH ₂ — Ethyl- • CH CH ₂CH₂— Propyl • (CH₃)₂CH—Isopropyl • CH CH ₂CH ₂CH ₂— Butyl • CH CHCH CH ₃— Sec-butyl • (CH₃)₂CHCH ₂— Isobutyl • (CH₃)₃C— Tert-butyl 5. Know how to draw skeletal structures • Note: Carbons and hydrogens will be present but not written- you will have to know their placement. Carbon is at each point. Butane: C4H10 (There are 4 carbons and 4 points) • • The formula will look like: • The skeletal structure will look like this: 9 Sunday, September 11, 2016 6. Know how to draw Newman Projections and determine relative stability 7. Know how to predict relative stability of cycloalkanes 1. More equatorial conformation will improve stability 8. Identify possible chair conformations of a cyclohexane ring (when given the name or planar structure) and identify stability 9. Know how to identify atoms that are axial and equatorial or cis and trans 1. Cis: CH3 (two methyl groups) are on the same side of the ring 2. Trans: CH3 (two methyl groups are on opposite sides 10. Know how to identify functional groups • Alkyl halide: Contains one or more halogens • Alcohol: • Replace suffix from -ane to -anol • OH attached 10 Sunday, September 11, 2016 • Amine: 11.Know how to identify the functional groups as primary, secondary, and tertiary 11 Sunday, September 11, 2016 • Primary: Carbons attached to one other carbon • Secondary: Carbons attached to two other carbons • Tertiary: Carbons attached to three other carbons 12. Know the IUPAC name for alkyl halide • “-amine” 13. Know how to name/ identify three types of non-covalent interactions 1. Electrostatic 2. Van der Waals Forces 3. Hydrophobic Effects 14. Know how to put compounds in order by relative boiling point, based on structure 12 Sunday, September 11, 2016 • Branching will lower boiling point • More branches = Lower boiling point • Boiling point increases with more carbons 15. Predict if a compound will be able to form hydrogen bonds • Hydrogen bonds are formed with: • Oxygen • Fluorine • Nitrogen 13 Sunday, September 11, 2016 Answer Sheet 1A. Try drawing BCl₃ and NH ₄⁺ A. 2B. How would you write C₃H₈O as a condensed structure? A. (CH₃)₂CHOH 14


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