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WSU / Chemistry / CHM 1240 / What is halogenation?

What is halogenation?

What is halogenation?

Description

School: Wayne State University
Department: Chemistry
Course: Organic Chem 1
Professor: Regina zibuck
Term: Summer 2015
Tags: Wayne State University, Chemistry, and Organic Chemistry
Cost: 50
Name: Wayne State CHM 1240 Exam 4 Study Guide (Ch. 9-11)
Description: Hello Everyone! This study guide covers all the types of reactions plus a few mechanisms from chapters 10 and 11 in preparation for exam 4. Includes, hydroboration oxidation, oxymercuration demurcuration, ozonolysis, carbene, epoxides, etc. Hope it helps!
Uploaded: 04/13/2016
6 Pages 113 Views 4 Unlocks
Reviews


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What is halogenation?



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alkenes

Ch. 10 Reacions Halogen okon: Halogen adds to most stable carbocahon.

His the electrophite H-Br

H electrophone always Br attacks (wl more n.

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© Hydroboration Oxidations

Antimarcov nikov rule- electrophile ques to carbon with most hydrogens. Boron is electrophile. Thus H goes to more stable posi ion or the one with less Hs thus anti markounikov.


What is the conversion of an alkene to alkane?



If you want to learn more check out What is logrolling? why does it occur?

1. BH3 2.4201008 Y BH2 MOHL

Wawenatogenahon mi non parlarang solent - add anti

x-x

no stereochem caly

necess. 5 halonydrin in participating solvent add anti but no sterea If you want to learn more check out Who was the prime ministers' in 1951-53?

necessary

X is the electrophile X -X H2O

OH X-X , ROH


What is the formation of exopide using peracid?



OCH3 1 Conversion of alkence to alkane in the presence of metal (Pd).

and carbon and hydrogen

removes the double bond.

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CH3OH crudys

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Pd, L

) Oxymerwon-demwuations Markovikov orientahon and

stereochemistry =NIA, no rearrangement.

1. Hg (OAch 2. Na BHY If you want to learn more check out How did economic dissatisfaction contribute to the cold war’s end?

бH

9

Formation of epoxide using peraud

Syn stereochem when

applicable

+ CH3C0001 - ozonolysis: cut double bond

1

in half and replace with

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Study SOLO Don't forget about the age old question of How much money do women make for every dollar a man makes?

reductive workup Don't forget about the age old question of How to predict the covalent bond strength?

2. NaBtly or

LATHU oxidative

2.H2O2

"UHHO 1 Carbene Carnene (A) takes place of double bond. Don't forget about the age old question of What is the best formulation to get to the insect?

p + H2CN2 ny 12 creation of diol

konoy

OH syn stereochem. or osoyup B Another form of corbene

O

HCC

kot

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(14) Epoxides in Acidic medium Nugues to carbon which

can generate most stable nucleophile. Only matters in asymmetric epoxides.

GH-

XX OH O

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H300

H/ROH

VOR

OH

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-(15) mechanism for epoxide reachon in acidic medium

coH2 H Hohe

CB

OH

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OH

studysous

RO-HT

ECB OH

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Stud

OR

OH

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16 Epoxides in basic medium: Nu aHacks (

wl more Hs.

9

NaOCHy

you OCH

01

YOH

OH

NANZ

() Study Soup

LiAlHy

XOH N3

Mechanism

for epoxide reaction

in basic medium

-

y

Nu work

WORK

you Nu

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udy Soul

*

Use

acidic medium/ basic

only

for

asymmetric

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epoxide

Reactions wi rings

are very similar!!

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CHM 1240 - Work Sheet 11

Predict the major producto

Predict the major product

Y H

AG-OA a

اسرار اي اهلا

Nobily

on

Agon

et

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NGOH

H2

Paan

H-X

H2O*

Study

"

always get more substituted

dicohol OH

X = CI, Brdihalogenation 1) Ag(OAC)2, H20

x add unti x Lo stu 2) NaBH4

Colar alcohol un carbon wl more hora

less SU

1) BH3

so halohydrin OH 2) H202, OH MAN Nilok w

CH,CO3H

markoff Nirof way

ayse CF2CO3H

*deckrohale goes to

(wl more is. Halde attacks mure subscured carbon..

carbushun sakume Ve so fuck for shifts.

I l

nalohudren

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or

ROHO

Talispahing

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R

H

spor

© non porta paling suivent

W no carbocanions

- W

on x

h

allide atracks from top or bottom.

x

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ogens, solvent (08.00) goes to our

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* halide goes to carbon wi? more h less 5

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Stud

You

H2

curbocation

a formed

9

Parc

H-X

H2O+

X = CI, Br

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x2 add anti

1) Ag(OAC)2, H20 2) NaBHA

CCIA

non participahing X2 add anti

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1) BH3 2) H2O2, OH

H20

antimarronkov

CH3CO3H

OH

ROH

or

X

CF3CO3H

OM

) Study Soup

(OHBH

) Study Soup

) Study Soup

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e Electrophilic 90

Cwlwu H.

V

Predict the major product

HS

Substrate

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Reagents

NA H-CI

NU=cl

Br2 in CCIA

OM

Br2 in H20

OH = Eu

EN=C

CI,

CH3OH

NU=UCH3

At

dirici

huocH3

OH

023898815880

oss

orodhadora 8 old87197018181810

8 8 0

NU=0H

HO

1) Mg(OAC), H20

2) NaBHA

» MOTOC), 4,0

ou

ASS

1) BH,

2) H202, OH

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CH,CO2H

or

CF.COM

Hz

Pd/C

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Stud

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