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by: Herta Weber

FundamentalsofOrganicChemistryI CHEM202

Marketplace > Pennsylvania State University > Chemistry > CHEM202 > FundamentalsofOrganicChemistryI
Herta Weber
Penn State
GPA 3.97


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Class Notes
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This 0 page Class Notes was uploaded by Herta Weber on Sunday November 1, 2015. The Class Notes belongs to CHEM202 at Pennsylvania State University taught by StevenWeinreb in Fall. Since its upload, it has received 35 views. For similar materials see /class/233150/chem202-pennsylvania-state-university in Chemistry at Pennsylvania State University.


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Date Created: 11/01/15
Summary of Reactions Which Will Appear on Exams 1 COMBUSTION OF HYDROCARBONS ALKANESALKENESALKYNES etc CXHy Xy402 gt xco2 y2H20 heat C10H20 gt this is the only reaction you will need to balance for all others only the organic products required 2 FREE RADICAL HALOGENATION OF ALKANES light or light CH4 CI2 gt CH3Cl HCl heat CH3CH3 Br2 gt CH3CH2Br HBr you need to know the mechanism 3 HYDROGENATION OF ALKENES H H metal catalyst H H H H CC Ni Pt or Pd I l CC R R39 H2 R R39 H H CH3 metal catalyst Ni Pt Pd CH synaddition H 3 of hydrogen 2 CH3 CH3 you need to know the mechanism cis product 4 ADDITION OF HX TO ALKENES H Rquot H X CC HX HI IR c c R R39 R R39 X Cl Br I X OH H2804 catalyst required hydration Markovnikov addition you need to know the mechanism 5 ADDITION OF X2 TO ALKENES H H H X X H Czc XX I I C C R RI R39 X Cl Br CH3 CH3 X XX gt X antiaddition of halogen CH 3 CH3 you need to know the mechanism trans product 6 DIHYDROXYLATION OF ALKENES H H n04 H OH OH H CC cold NaOH i I R R R R39 OH CH3 KMnO4 OH cold NaOHHZO CH synaddition 3 of OH groups CH 3 CH3 cis prod uct 7 OXIDATIVE CLEAVAGE OF ALKENES H Rquot an04 H Rquot CC in H20 H CO OC R R R R an aldehyde a ketone further oxidation HO CO R a carboxylic acid 8 FREE RADICAL POLYMERIZATION OF ALKENES heat CH2fH R39oOR39 gt R39OCH2CHCH2CHnetc R R R you need to know the mechanismin packet 9 HYDROGENATION OF ALKYNES metal catalyst H H Ni Pt or Pd R CEC R39 gt C C syn addition 1H2 R R you need to know the mechanism cis product 10 HALOGENATION OF ALKYNES X2 CZC anti addition X R39 R CEC R39 you need to know the mechanism X Cl Br trans product 11 HX ADDITION TO ALKYNES R H HX R CEC H C C X H you need to know the mechanism X Cl Br I Markovnikov addition 12 HYDBATION OF ALKYNES H20 R H R CH3 R CEC H gt CC gt C H2804 HgSO4 HO H 0 catalysts an enol unstable a ketone Markovnikov addition 13 ALKYLATION OF TERMINAL ALKYNES NaNH2 R oEo H gt B CEC Na R39CHZX gt R CEC CHZR39 or 2 or 3 alkyl halides do not work or Cst R CEC CHs XCI Br I 14 HALOGENATION OF CONJUGATED DIENES 1 2 s 4 X2 1 2 s 4 1 2 s 4 CH2CHCHCH2 gt CIHgCIHCHCH2 CHgCHCHH2 X X X X X Cl Br 1 2addition 14addition 15 HX ADDITION TO CONJUGATED DIENES 1 2 3 4 1 2 s 4 H X 1 2 s 4 CH2CHCHCH2 gt CH2 CH39CHCH2 CIHgCHCHH2 H X x 12 addition 14addition XCI Br 16 ELECTROPHILIC AROMATIC SUBSTITUTION E reagents X gt X halogenation CI2FeCI3 or AC3 cat E CI Br2FeBr3 or AIBr3 cat E Br nitration HON02HZSO4cat E NO2 sulfonation HOSOSH E SOsH FriedeICrafts alkylation RCIAICI3 cat E R 0 FriedeICrafts acylation 5 IAICI3 cat E OH R CI you need to know the mechanism and the directing effects of various substituents quotXquot 17 AROMATIC SIDECHAIN OXIDATION TO BENZOIC ACIDS CHR KMno4 CO2 Fquot H20 heat X gt X R R39 alkyl or H 18 AROMATIC RING REDUCTION TO CYCLOHEXANES R 3H2 R Pt cat gt high pressure 19 REDUCTION OF NITRO GROUPS TO ANILINES N02 3 NH2 X gt X 20 CONVERSION OF SULFONIC ACIDS TO PHENOLS NaOH OH SOsH 300 00 X gt X then H30 21 REDUCTION OF CARBONYL COMPOUNDS TO ALCOHOLS Q 0 NaBH4 II ethanol C gt R CHZOH R H or I LiAlH4 ether Prlmary aICOhOI aldehydes then HSO O NaBH4 OH I ethanol i R R39 or R I R LiAlH4 ether H ketones then H30 secondary alcohol 0 LiAlH4 ether II then H30 C gt RCHZOH R39OH R OR39 primary alcohol esters you need to know the mechanism of aldehyde and ketone reductions but not esters 22 OXIDATION OF ALCOHOLS TO CARBONYL COMPOUNDS 0 o CrOs or Na2Cr207 C C RCH OH primary alcohol aldehyde carboxylic acid 0 PCC I I RCHZOH gt C PCC pyrIdInIum chlorochromate R H primary alcohol aldehyde OH I CrO3 39339 C or Na2Cr207 C I gt R I R R R39 H ketone secondary alcohol OH I Cros C or Na2Cr207 R I R gt no reactIon Rquot tertiary alcohol You need to know the mechanism of oxidation of alcohols to aldehydes and ketones with CrOs 23 CONVERSION OF ALCOHOLS TO ALKYL HALIDES SOCI2 ROH RCl PBrs R OH gt RBr 24 WILLIAMSON ETHER SYNTHESIS gt ROCH R39 Na or R oH2 X 2 NaH ROH gt R0 Na 0F CH3X FIooH3 XCBr 2 or 3 alkyl halides do not work in this reaction 25 POLYMERIZATION OF EPOXIDES base cat B R R H C CH I 2 B39CH2 C HOnCH2CHOetc R you need to know the mechanism4n packet 26 ACIDBASE REACTIONS OF CARBOXYLIC ACIDS PHENOLS AND AMINES NaHCO 39339 or NaOH3 39339 gt o o R OH R HCI or H2804 O39 Na NaOH but not NaHCOs gt ArO39 Na ArOH HCI or H2804 HCI gt R3N R3NH CI39 lt 27 ALKYLATION OF AMINES R X RNCHZX gt R39 N CH2R39quot R l Rquot R39 N 2 or R X Rquot O O O CH3X gt FgNCH3 1 20r3 XCBrl n R R39 Rquot alkyl H aryl R a quaternary ammonium salt 2 or 3 alkyl halides do not work in this reaction Ph Ph I Ph I CHsCHzl I NaOH I H NI gt H N CHZCH3 gt 2 N CH2CH3 CH3 Hs only if there CH3 is at least one H on the nitrogen 28 SYNTHESIS OF GRIGNARD REAGENTS AND ORGANOLITHIUM COMPOUNDS ether RX Mg gt RMgX Grignard reagent alkane solvent RX 2Li gt RLi LiX XC Br I 29 REACTIONS OF GRIGNARD REAGENTS AND ORGANOLITHIUM COMPOUNDS RMgX H20 or gt RH RLI O RMgX CO2 or gt RCOH RLi then H30 a carboxylic acid 0 R OH R39Mg39x M then H30 C or R39CH gt R H R Li aldehyde 20 alcohol R OH R39MQ39X then H30 or R39CRquot gt RlCRquot RLi ketone 3 alcohol you need to know the mechanismin packet 30 ELIMINATION OF ALKYL HALIDES TO ALKENES H X H R H R NaOH II3 C C NaX H R H R XCBr you need to know the mechanism 31 HYDRATION OF ALDEHYDES AND KETONES H20 0 acid or base HO OH H catalyst C RCH gt R H aldehyde H20 0 acid or base HO OH catalyst R39CR gt C R39 R ketone you need to know the mechanismin packet 32 REACTIONS OF ALDEHYDES AND KETONES WITH ALCOHOLS RHOH HO OR 0 base quot ll catalyst C h I a emiaceta RCH gt R H aldehyde 0 RquotOH base HO ORquot ll catalyst R39CR gt RlCR ahemlketal ketone 2RquotOH R OR 0 acid quot quot II catalyst C RCH gt R H an acetal aldehyde 2RquotOH acid Ruo ORquot II catalyst R39CR gt C a ketal R39 R ketone you need to know the mechanismin packet 33 CYANOHYDRINS FROM ALDEHYDES AND KETONES O HCN HO CN NaCN C RCH gt R H aldehyde HCN II NaCN HO CN R39CR C ketone R R you need to know the mechanismin packet 34 REACTIONS OF ALDEHYDES AND KETONES WITH AMINES AND DERIVATIVES 0 NZ II H cat C ZNH2 gt C R H R H aldehyde 0 NZ II H cat C Z NH2 gt C R R R R39 ketone Z OH NHPh alkyl aryl you need to know the mechanismin packet 35 OXIDATION OF ALDEHYDES TO CARBOXYLIC ACIDS O Ag1 0 NH4OH T939IeI S C C OXIdatIon R H R OH 39339 CU2 O Fehling or C gt E Benedict oxidation R H mm mltZImmm Ou OgtmwOXltEO gtOU OIrOmEmm gtZU gt2IltUEUmm O O t moQN 391 m 3 0I E O O O O m m m mOOI mOOm lY m 0 m 0 O Imo o V o 9 m o m o o o o Inc M o o o E O m m OI mm mmgt0OZ Ou OgtmwOXltEO gtOU OIrOmzumm gtZU gtZIltUmUmm ltltI gtOOIOum O O no O V O IO m o m om m mmnmw no 39 FISCHER ESTERIFICATION OF CARBOXYLIC ACIDS TO ESTERS O O H Hcat H R39OH C H20 C R OH R OR an ester must remove water you need to know the mechanism 40 HYDROLYSIS OF ESTERS TO CARBOXYLIC ACIDS AND ALCOHOLS i ll H cat I c H20 gt C ROH R OR39 R OH O O 0 HCI ii C NaOH gt R39OH C R OR R o Na R OH you need to know the mechanisms for both of these 41 AMINOLYSIS OF ESTERS TO AMIDES o O H HNR heat Q RIOH C quot2 gt R OR39 R NR 2 an amide Rquot H alkyl aryl 42 REACTIONS OF GRIGNARD REAGENTS AND ORGANOLITHIUM COMPOUNDS WITH ESTERS TO FORM TERTIARY ALCOHOLS OH O 2 R M9 X then H30 I Q or gt C R39OH R OR39 2 RquotLi R FI quot Rquot you need to know the mechanism 43 REACTION OF CARBOXYLIC ACID CHLORIDES AND ANHYDRIDES WITH AMINES 39339 0 C HNR39 gt R C39 2 RCNR an amide II II II II C C HNFII gt C C R O R 2 R NR392 R OH R39 H alkyl aryl 44 HYDROLYSIS OF AMIDES HCI 39339 H20 0 heat C Q HNR2 R NR392 R OH NaOH 0 H20 0 ll heat HNRI C C 2 R NR392 R o Na you need to know the mechanism


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