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Lecture |
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1 |
Organic molecules in your everyday life |
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2 |
What is an organic molecule? |
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3 |
The difference between atomic numbers and atomic mass |
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4 |
Shells, orbitals and types of ions |
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5 |
3 rules about orbitals you need to know |
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6 |
The probability of finding electrons in a given place |
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7 |
What’s the difference between sigma and pi bonds |
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8 |
What’s the difference between atomic and molecular orbitals |
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9 |
Single bonds, double bonds, and triple bonds |
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10 |
How Nobel gases are related to the octet rule |
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11 |
The most important parts of the periodic table for organic chemistry |
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12 |
The octet rule |
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13 |
What is a valance electron? |
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14 |
What is the difference between valance and octet electrons? |
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15 |
Calculating formal and net charge |
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16 |
Calculate the formal charges of ALL atoms |
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17 |
How bondline is different from Lewis Structures |
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18 |
How to use Organic Chemistry to make Lewis Structures easier |
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19 |
How to interpret condensed structures |
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20 |
The difference between saturated and unsaturated molecules |
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21 |
What index of hydrogen deficiency is |
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22 |
How to use IHD with molecular formula |
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23 |
What is a constitutional isomer? |
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24 |
The rules you need for resonance |
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25 |
Common ways to move arrows in resonance |
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26 |
How to determine which structure is most stable |
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27 |
How carbon creates 4 partially-filled orbitals |
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28 |
Using bond sites to predict hybridization |
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29 |
Molecular Geometry Explained |
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30 |
How to tell the difference between ionic, polar and covalent bonds |
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31 |
How IMFs are related to melting and boiling points |
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32 |
How hydrogen bonding works |
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33 |
How dipole-dipole forces work |
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34 |
How Van der Waals forces work |
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35 |
Understanding “like dissolves like” |
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36 |
Introducing common solvents and other molecules in organic chemistry |
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37 |
Why we need functional groups |
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38 |
Recognizing different types of hydrocarbons |
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39 |
How to assign degrees to carbons and hydrogens |
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40 |
Recognizing alkyl halides |
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41 |
How to recognize alcohols, amines and ethers |
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42 |
How to recognize carboxylic acids, amides and esters |
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43 |
The difference between aldehydes and ketones |
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44 |
How to recognize nitriles |
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45 |
The difference between phenyl and benzyl groups |
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46 |
Recognizing acyl chlorides and anhydrides |
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47 |
What you need to know about types of chemical reactions |
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48 |
Recognizing Acid-Base Reactions |
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49 |
How to tell if a molecule will be reactive or not |
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50 |
How to tell if charged molecules will react as nucleophiles or electrophiles |
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51 |
How to tell if uncharged molecules will react as nucleophiles or electrophiles |
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52 |
Learning the rules of electron movement |
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53 |
Why we need to break bonds sometimes |
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54 |
The Lewis definition of acids and bases |
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55 |
The Brønsted Lowry definition of acids and bases |
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56 |
Equilibrium constant and conjugates |
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57 |
Why we use pKa instead of pH |
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58 |
The relationship between equilibrium constant and pKa |
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59 |
The pH scale vs the pKa scale |
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60 |
The 12 pKa values you want to memorize because they're important! |
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61 |
The 3 steps for determining the direction of acid and base equilibrium |
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62 |
Why we need factors affecting acidity and when to use them |
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63 |
Understanding the Element Effect |
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64 |
Understanding the Inductive Effect |
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65 |
Understanding resonance effects Which of the following –OH groups would be more acidic and why? |
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66 |
Understanding hybridization effects |
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67 |
The different parts of an IUPAC name |
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68 |
Learning Alkane Prefixes up to 12 Carbons in Length |
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69 |
Naming the root chain |
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70 |
How to determine the direction of the root chain |
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71 |
How to identify and locate branches (substituents) |
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72 |
Proper name ordering and punctuation |
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73 |
Understanding Non IUPAC Substituents |
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74 |
How to find the root name for cycloalkanes |
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75 |
Why it is okay to omit a single location for monocyclics |
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76 |
What is a bicyclic molecule? |
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77 |
The two types of bicyclic molecules |
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78 |
How to name a bridged bicyclic |
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79 |
How to name alkyl halides |
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80 |
How to name alkenes and alkynes |
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81 |
How to name alcohols |
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82 |
Old School vs. New School Naming |
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83 |
How to name different types of double bonds or rings |
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84 |
Why we need to use the EZ naming system |
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85 |
What does E and Z stand for |
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86 |
Understanding what a conformer is |
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87 |
How sigma bond rotation is visualized |
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88 |
The energy states of 3 different Newman Projections |
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89 |
Six Steps to Drawing Newman Projections Step 1 |
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90 |
Six Steps to Drawing Newman Projections Step 2 |
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91 |
Six Steps to Drawing Newman Projections Step 3 |
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92 |
Six Steps to Drawing Newman Projections Step 4 |
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93 |
Six Steps to Drawing Newman Projections Step 5 |
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94 |
Six Steps to Drawing Newman Projections Step 6 |
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95 |
4 Values You Should Memorize |
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96 |
Understanding Heat of Combustion |
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97 |
Shape and strain make alkanes unstable |
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98 |
What is angle strain? |
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99 |
What is torsional strain? |
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100 |
What is a chair conformation? |
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101 |
How chairs flip from one conformation to another |
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102 |
How to draw chairs |
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103 |
How to distinguish cis from trans |
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104 |
Axial or Equatorial: Which position is better? |
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105 |
The 3 important factors when drawing chairs |
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106 |
How to determine the stability of a declin |
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107 |
Draw the following declin as a chair conformation in the most stable conformation |
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108 |
Determining when molecules are different |
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109 |
Determining when molecules are constitutional isomers |
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110 |
What is chirality? |
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111 |
How and when to use the internal line of symmetry test |
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112 |
What is a stereocenter? |
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113 |
The difference between chiral and trigonal centers |
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114 |
Why stereoisomers need their own naming system |
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115 |
R and S Naming - Step 1 |
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116 |
R and S Naming - Step 2 |
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117 |
R and S Naming - Step 3 |
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118 |
R and S Naming - Step 4 |
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119 |
R and S Naming - Step 5 |
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120 |
Using chiral centers to predict types of stereoisomers |
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121 |
How to predict the total number of stereoisomers |
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122 |
Recognizing chiral molecules with zero chiral centers |
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123 |
Determining if allenes are chiral or not |
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124 |
Determining if substituted biphenyls are chiral or not |
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125 |
Defining meso compounds |
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126 |
The 3 rules of meso compounds |
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127 |
Three types of disubstituted cycloalkanes |
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128 |
Cis-1,2-Disubstituted Cyclohexane A controversial exception |
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129 |
Different atoms or different connectivity |
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130 |
Same atoms, same connectivity, 0 chiral centers |
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131 |
Same atoms, same connectivity, 1 chiral center |
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132 |
Same atoms, same connectivity, 2 or more chiral centers |
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133 |
Same atoms, same connectivity, 1 or more trigonal centers |
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134 |
When to use R and S, when you don’t have to |
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135 |
Introduction to different projections |
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136 |
How to convert Fischer projections into bondline structures |
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137 |
R and S rule for Fischer Projections |
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138 |
Specific rotation vs observed rotation |
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139 |
How to calculate enantiomeric excess |
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140 |
How to solve for the percentage of each enantiomer |
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141 |
Breaking down the different terms of the Gibbs Free Energy equation |
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142 |
How to calculate enthalpy using bond dissociation energies |
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143 |
Explaining what entropy is |
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144 |
Defining the Hammond Postulate |
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145 |
Determining Carbocation Stability |
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146 |
Understanding why carbocations shift |
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147 |
Remembering general patterns of reactions |
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148 |
Nucleophiles and Electrophiles can react in Bronsted Lowry Reactions |
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149 |
Nucleophiles and Electrophiles can react in Lewis Acid Base Reactions |
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150 |
How to use the factors affecting acidity to predict leaving group ability |
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151 |
Drawing the SN2 Mechanism |
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152 |
Drawing the SN1 Mechanism |
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153 |
Why highly substituted leaving groups favor SN1 |
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154 |
How do we predict if the mechanism is SN1 or SN2 |
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155 |
Drawing the E2 Mechanism |
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156 |
The number of unique β carbons helps predict the number of possible products |
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157 |
The number of unique β carbons in an anti-coplanar arrangement predicts the total number of products |
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158 |
Drawing the E1 Mechanism |
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159 |
Understanding the properties of E1 |
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160 |
General format of reactions and how to interpret solvents |
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161 |
The difference between protic vs. aprotic solvents |
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162 |
The 3 important leaving groups to know |
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163 |
Overview of the flowchart |
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164 |
How to predict SN2 and E2 mechanisms |
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165 |
How to predict SN1 and E1 mechanisms |
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166 |
Understanding trends of alkene stability |
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167 |
Defining Zaitsev’s Rule |
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168 |
Using a Free Energy Diagram to explain thermodynamic vs. kinetic products |
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169 |
The dehydrohalogenation mechanism |
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170 |
General features of double dehydrohalogenation |
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171 |
Understanding how to convert terminal alkynes to alkynides |
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172 |
Using double dehydrohalogenation to perform alkynide synthesis |
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173 |
The definition of hydrogenation |
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174 |
Using Catalytic hydrogenation or Wilkinson’s Catalyst to turn alkynes to alkanes |
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175 |
Using Dissolving Metal Reduction or Lindlar’s Catalyst to turn alkynes to alkenes |
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176 |
General features of acid catalyzed dehydration |
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177 |
Dehydration of 1° alcohols The E2 Mechanism |
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178 |
Dehydration of 2° and 3° alcohols The E1 Mechanism |
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179 |
An extra note of caution with 1° alcohols |
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180 |
General features of dehydration with phosphoryl chloride |
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181 |
Features of Addition Mechanisms |
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182 |
How to add to asymmetrical double bonds |
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183 |
General properties of hydrohalogenation |
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184 |
General properties of acid-catalyzed hydration |
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185 |
General properties of oxymercuration-reduction |
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186 |
A worked example of the acid catalyzed oxymercuration reduction mechanism |
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187 |
General properties of hydroboration oxidation |
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188 |
Catalytic Hydrogenation: Mechanism |
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189 |
General properties of halogenation |
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190 |
General properties of halohydrin formation |
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191 |
A worked example of the halohydrin mechanism |
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192 |
General properties of epoxidation |
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193 |
The mechanism of how halohydrins make epoxides via intramolecular SN2 |
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194 |
Acid Catalyzed Epoxide Ring Opening |
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195 |
Syn Vicinal Dihydroxylation |
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196 |
Ozonolysis |
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197 |
General properties of double addition reactions to alkynes |
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198 |
Double hydrohalogenation of alkynes |
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199 |
Double halogenation of alkynes |
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200 |
Vinyl alcohols yield tautomers |
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201 |
Markovnikov addition of alcohols yields ketones |
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202 |
Heterolytic vs Homolytic Bond Cleavage |
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203 |
The radical stability trend |
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204 |
The one reaction that alkanes will actually undergo |
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205 |
Radical Chain Reaction Mechanism |
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206 |
Using the Hammond Postulate to describe radical chlorination |
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207 |
Radical selectivity: Lilo vs. Dutchess Kate |
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208 |
Overview of Hydrohalogention |
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209 |
General features of Radical Polymerization |
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210 |
The general mechanism of Allylic Halogenation |
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