Ericpdotutoring.weebly.com E. Do; epdo@ucdavis.edu

HBR s BrXt

Thermodynamic Product

Dcl A BIP BrD

Thermodynamictrr rIf I M35 hu 11 1 Racemic

v t

x NCS hu NaCHzClz

Rearrangementzr tomoresubb1 NBS hu Wo 2 suzan alkeneoccurs2 H2O b unless cold

1 NBS Hu WN 2.1Mgetco3 Br

Rearrangement1 NCS hv COLD tothemorestable

1 2 LDA alkenedoes notoccurw Ncs orcold

41v Ary1 HCl b W r ai y2 2 Li etzo HoH

Racemic3 3.1 TY Ann1 04 11301 H2O 4 runTH

Note from Dr. Nasiri: “Free radical bromination is very selective towards the most stable product. Free radical chlorination is not as selective” -However, in this question, the rearranged product is the same as the non-rearranged product

N Bra s menter

Br racemic

KY1 NBS BrIV 2 LDANote adiene

CHE Il rI CHA Il Ie s

IN Il s TT

AdachiN 1 Nao 11 I t En

B NINA 1kW

OCH 0440 From weeks lectures

y II s h EPEe

I TT Il l EN I KewX o core

oats Fromweeks lectures0 D A EN E'T

Ken anKew ew

cparas

a w th EnI t st

JI Diene lockedin

1 I 11 NR s transiI s mustbe S cisN 2

outs 11 outs trickyquestionbutsince

if i K IEEEnT.EE ieA No resonancestructures

EN 61.0I CFA µmN02 goes NozisI 1 am s III IIT ie bI N abondI whilecooats Knw och doesno

II NHz few Ewaheat t EN corth

43 Seewebsite

FX Foots EN EEEmyMheat CH

r n buli It fiNR

cyclobuteneA is notstableunderheat

nu i it hE irainswere nottaught for5522019

CI

w Dd r RE'n

A xD TEDH D b p I l t Il lDao DO I U

Br CN

µ NaCN SN2

Cl SNIHon a Anons

OHBr s.IE jFE i

siEome

5 3

4 1 heat a M1

CN

Ne Il o r KI

EF

I Most reactive

nor oats IkeIl 11 11 11CF LOCH

YE E N Moat Em in i

II ft EI EI oA A AntiA AntiA non A

citya o

NO

cH3 OCH

ITN

Diels-Alder Questions and other multiple choice 1.) Rank the following by the rate of reactivity with 1-methoxy-1,3-buta-diene: 2.) Rank the following by the rate of reactivity with 3,3,3-trifluoropropene: 3.) Which of the following is the most reactive SN1 substrate? 4.) Label the following as either aromatic, anti-aromatic, or non-aromatic: 5.) Draw the diene and dienophile that will result in the following products under thermal conditions: 6.) Draw the molecular orbital diagram for the transition state of the Diels-Alder reaction:

v N N

liking naw AlfCHz

NOH Br

e27 ftp.r i SwaOR Nier

fHBR F HBRx s

or ii Yea at

N o XBrchu

n isYer

N o u

Mr

m Un

Ni ma

2 HsOt

MrErnani na.it

N N

I Een7 x ii

OBr

i N 2

in oo IIIo

aOH

no

a exIii

iift

Nh

Br Oo t Nntr