ORGO EXAM 2 PRACTICE QUESTION GUIDE
ORGO EXAM 2 PRACTICE QUESTION GUIDE CHEM 210
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This 22 page Study Guide was uploaded by Lauren Notetaker on Thursday October 1, 2015. The Study Guide belongs to CHEM 210 at Pennsylvania State University taught by Maslak in Fall 2015. Since its upload, it has received 209 views. For similar materials see Organic Chemistry I in Chemistry at Pennsylvania State University.
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Date Created: 10/01/15
reserpine 9 H CH3 1 39 i f 0 CI 3 j H 0ng H30 xH CI In CI H30 H b Lecture 8 amp Lecture 9 O Omlo M 0 x fo bf H W I h O 10 I hm hm IO Io 0 Io 6 FT 3 3 W Am Io 0 0 IO 10 g F d 10 E EBm A is mesa and B is chiral A and B are diastereomers A and B are not superimposable A and B are enantiomers COP Lecture 10 a b E 1 Hi BID BID lt39Br HM 3Br H a I C 1 Brquot G Br Hf C39ltBr HEB Brquot Brquot C Br 1 0 AVL Kk F 1 C1HCCH CHC1 CHCHC1 HO HO H i H 1N0 g CHCHCHCOOH Lecture 11 CH3 H H30 CH3 H30 CH H CH3 H30 CH H H 1 2 Energy kcaImo 4 I I I I I I I 180 120 60 O 60 120 180 torsiona anale H3 H3 H30 C H30 H30 HSC CHS H CH3 H3C CH3 H30 CH3 H CHE H H H30 H H30 H H H H30 CHE CH3 CH3 H H 2 CH3 a b c d e torsional angle H H H H H7 a HEEIH b ag 0 EELH d 3 e H H H H H H CH3 back carbon CH3 Hgm b rotation by 120D H3C CH3 H30 H H3C H CH3 H CH H Br CH3 H CH3H H Br CI H30 Br CH3 Brgfak H30 Cl Br CI H CH3 H H H30 C H CH3 CH3 CI CH3 8 b C d e a butane H H b 2methy1butane c 23dimethy1butane Energy kcalmol 4 HLJ 2 H H d 223trimethy1butane r39Ju H H e 2233tetramethy1butane 1 180 120 60 0 60 120 18C torsional angle Et Et Et Me H iMe H iiMe Me H H Me H Me Me H Me H Et H Et Et Et Et 8 b C d Lecture 12 Act A gt B gt Act B gt A AGA gtBltAGB gtA a b 1 0 AG A gt B AGt B gt A D 60 120 180 240 300 360 reaction coordinate dihedral angle step 1 B step 2 reaction coordinate O anquot nu h d a IV represents the highest energy intermediate V39 DDquot nu h d b 111 is more stable than VI Dena h d c 11 represents the most stable transition state gamma h H d The overall reaction from VII to I is exergonic Free Energy kcaImol o s ro w A 01 c I co co V reaction coordinate reaction coordinate H H H HCH H CH3 H30 H H 3 Zia H3 59 H H CH3 H H CH3 HH C943 HH 6H3 A B c D All four are energy minima structures All four are transition state structures A and B are energy minima structures and C and D are transition state structures A and B are transition state structures and C and D are energy minima structures 999 Energy 10 9 A8 6 E7 m6 0 x 5 a 254 LIJ3 cu 92 LL 1 0 reaction coordinate Free Energy kcalmol reaction coordinate Reaction coordinate Lecture 13 A B C mwk AHc 960 kcallmo AHC 1520 kca mmo AllIC 630 kcaHmo l f I H a The hybrids making the C C bonds have increased s character as compared to those of ethane f I H H b The hybrids making the C C bonds have increased p character as compared to those of ethane f I H H c The bend C C bonds have increased electron density above and below the plane of carbon ring like 139I bonds f I H H d The hybrids making the C C bonds have more s character than the hybrids making the C H bond in this compound IH2CCH2g H Clg gt H3C CH2 C1l 11 H2CCH2g H OH1 gt H3C CH2 OH1 f 1 u n a I 18 endergonlc and II 15 exergomc f Iu H H b I is exergonic and II is endergonic H H 0 both I and II are exergonic H I d both I and II are endergonic gt ltgt Lecture 14 ring B H rIngA W 2 H H 1 0 CH 0 CH H7 3 ma a 567 3 H30 CH3 H30 A B c HHHHHHCIHCIHHHHCIH CWCI 9 H qu cWH H H H H H H H H a b C d H H 1 ring B H rlngA W 2 menu a is possible through a cyclohexane ring ip of ring A H H b is possible through a cyclohexane ring ip of ring B H c is possible through cyclohexane ring ips of both ring A and ring B H 3 H d is not possible by a conformational change CH3 mom iPr 4 1 iPr 2 gauche rel E 26 kcalmol 00 koaImol OH 3 HOWOH b HON C memo d H3CmOH H30 H30 Ho OH CH3 CH3 2 3H3 5 LLI D 5 LLI O 5 LL m 5 LL lt3 mInfomI A NI NIQHQNI Q fem A NI mIolomI av GI 0 Al NI oomI i ma 933 wIon mIOI m I I of q I I I0 I I I mIo Io Io I II I I IE I I 04 I 3 I I 0103 I 3 I I I I I I mIo I mIo I mIo fog 1r XI 5 mquotIo A Expected H30 CI CI 1 chCl Cl 1 2 3 4 A Competition H30 ch CI p Hsc CHS 3 1 3 5 4 H30 G gt HSC CI 0 CHBCI gt CH20I c I Br Cl gt Br Cl 11 Br CH4 gt HBr H30 111 C1 CH4 gt HCl H3C IV H3C Br Cl gt C1 H3C Br V H3C Br Cl gt Br H3C Cl r39Ju H H a Methyl bromide is the main product because reaction 11 is favored over 111 r39Ju H H b Methyl bromide is the main product because reaction IV is favored over V I m H H c Methyl chloride is the main product because reaction III is favored over 11 I m H H d Methyl chloride is the main product because reaction V is favored over IV f Iu H H e Methyl chloride and methyl bromide are produced in similar quantities Lecture 16 E E reaction coordinate reaction coordinate E E m reaction coordinate reaction coordinate F C O E NBShv rAA CCusoWa Br Br Br Br A B C D E CH3 CHSCI 1 T CH3 39CH2 CH3 PhKKCHS WANCH3 PhKFQHE CH3 CH3 CH3 A B C NBS MI W gt CCI4 solvent Br Br a W b W cWB d BVM X E R1 X R1 E R H1 X0 R1 R xH gt R CH2 R gt R 9 R 5 H H R2 1 2 3 4 5 5 6 m H H a The energy differences between 2 4 and 6 are largerwhen F is used compared to when I is used f In H H b The energy differences between 2 4 and 6 are smallerwhen F is used compared to when I is used r39Jn H H c The energy differences between 2 4 and 6 are the same when F is used compared to when I is used CI CI2 gt HCI hv 1 2 C39 3 BDE H X kcalmol H CN 130 H ON 1 19 H CHs 104 O I CH3390H2390H2 HBCACHQ h H a The energy differences between I and II are larger when Cl is the abstracting radical h d b The energy differences between I and II are larger when Br is the abstracting radical h d c The energy differences between I and II are the same for C10 and Br but different for F0 Dena h d d The energy differences between I and II do not depend at all on the identity of the abstracting radical quot a C1 HgC CHz CHg gt HCl CH32HC b Br H3C CH2 CH3 gt HBr H3C CH2 H2C DELI c F H3C CH2 CH3 gt HF H3C CH2 H2C d 1 HgC CHz CH3 gt CH32CHI H j J 21 HO t j b F0 33973 HcC1 H a dBr t i c1 t j 33 b4 05 d6 67 rt Elh Elh j
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