Survey of Organic Chemistry
Survey of Organic Chemistry CEM 143
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This 6 page Study Guide was uploaded by Ladarius Rohan on Saturday September 19, 2015. The Study Guide belongs to CEM 143 at Michigan State University taught by Karrie Manes in Fall. Since its upload, it has received 53 views. For similar materials see /class/207676/cem-143-michigan-state-university in Chemistry at Michigan State University.
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Date Created: 09/19/15
CEM 143 Summer 2009 Chapters 7 Study Sheet Alcohols Nomenclature CH OH OH OH 3 methanol or ethanol or 1propanol or 1butanol or methyl alcohol ethyl alcohol npropyl alcohol nbutyl alcohol or propan1ol or butan1ol AK kOH OH OH 2 butanol or 2 methyI1propanol or 2methyl2 propanol or secbutyl alcohol isobutyl alcohol tertbutyl alcohol or butan2 ol or 2 methylpropan1ol or 2 methylpropan2ol OH 0 7 W H OH OH 2 propen1ol or benz Ialcohol or cyclohexanol or y allyl aICOhOI cyclohexyl alcohol pheny39methanOI OH OH OH HO CI CI OH Br 0 phenol mbromophenol CI phydroxybenzoic 246trichlorophenol aCd caFDOXCYCNQ aCId gets prIorIty In naming Classification OH N 7OH OH PRIMARY SECONDARY TERTIARY Properties of Alcohols The boiling points of alcohols are significantly higher than their alkane counterparts despite the fact that their molecular weights are similar For example OH Propane 1propanol MW 44 MW 46 BP 42 C BP 785 C This phenomenon is due to the ability of 1propanol to hydrogen bond with itself whereas propane can only interact with itself through the much weaker van der Waals forces hydrogen 639 6 bond 5 5 5 6 0 O H N 5 10 N No H H kcamo two separate alcohol H 6 molecules 6 Each hydrogen bond is 5 to 10 kcalmol in energy To put that number in perspective a CC single bond is 86 kcalmol and an OH bond in water is 111 kcalmol So5 to 10 kcalmol doesn t seem like a lot but that s just for ONE hydrogen bond Imagine if you had 1 mole of water 6022 X1023 molecules 80 in water as well as in alcohols you not only have to supply enough heat to vaporize the molecules you also must have enough heat to break all the hydrogen bonds Acidity amp Basicity of Alcohols AcidBase Chemistry from CEM 141 o Ka F39I H H H H 9 H base acid conjugate conjugate acid base Ka acid dissocation constant productsreactants H30Cl HCl For water 0 o Ka Ii H H H H HQxH OH Ka18x103916 To make these really small numbers relate to the pH scale we use pKa values via the HendersonHasselbach equation f pHpK 10gH A 80 for water pKa log1OKa 158 These pKa values that we express here are the pH at which the acid is 50 dissociated or in other words when HA A 80 the lower the pKa value the stronger the acid and the higher the pKa value the weaker the acid A pKa of 158 for water means that we would have to be at a pH of 158 for 50 of the water to exist as hydronium and hydroxide the other half would still be water Now that we ve figured out water we can look at alcohols Alcohol pKa CH30H 155 OH 159 F FOH 124 F OOH No2 72 OOH OH I NO O2N O2N Synthesis of alcohols from Chapter 6 H20 H Br gt0r OH OH39 Reactions of alcohols 1 Substitution amp Elimination So far we have seen from Chapter 6 that Cl Br amp I can act as leaving groups These leaving groups leaved as negatively charged ions In the case of alcohols OH is a terrible leaving group on its own but we can make it a better leaving group simply by adding an H to the oxygen and making the leaving group H20 rather than just OH alone We do this using a strong acid OH gtH S H H Using this method we can perform substitution and elimination reactions Alkyl halides from alcohols using HBr HCI or HI AHgr C H OH gt Q gt Br H20 H Br39 Another way to get alkyl halides from alcohols is using SOCI2 or PBrs See below 30012 OH gt C Br3 OH Br These two reactions follow an 8N2 pathway therefore if the reaction is taking place at a chiral carbon there will be 100 inversion of stereochemistry Alkenes from alcohols fquot K H H H H804 2 Oxidation of alcohols Oxidation in the case of alcohols is increasing the number of C0 bonds For primary alcohols The use of CrO3 and HCI oxidizes primary alcohols 2 steps up from 1 C0 bond to 3 C0 bonds to the carboxcylic acid First the alcohol is oxidized to the aldehyde but the reaction does not stop and continues to the carboxcylic acid 0 O CrO HCI CrO HCI OH 4 H gt3 OH carboxcylic h ade yde acid To stop at the aldehyde a milder reagent must be used This reagent is called PCC which stands for pyridinium chlorochromate O NH LH aldehyde
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