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CORNELL / Chemistry / CHEM 3570 / chem 3570 prelim 2

chem 3570 prelim 2

chem 3570 prelim 2

Description

School: Cornell University
Department: Chemistry
Course: Organic Chemistry
Professor: Ganem prof. dichtel
Term: Fall 2016
Tags:
Cost: 50
Name: CHEM3570 Prelim #2 Study Guide
Description: Electrophilic addition reactions, stereochemistry, and chirality
Uploaded: 10/17/2016
6 Pages 9 Views 9 Unlocks
Reviews


Il less electronegarine atom in the day 4 more important for the leasin. UNS OF ALKENES WI HALOGEN


What is free radical measurement?



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PRELIM#2 STUDY GUIDE

ADDITION RUN'S OF AIKENES

DU

- carbon of double bond Wl Tewer alky, substitutes becomes bonded to less electronegative aroup - Electrophilic Center is the less electronegative atom in the double bond (electronegarivity is more important for leaving group).

ALKENES WI HALOGENS (C12, B12)

products are vicinal halides: laci compounas w halogens an adjacent

It - MOST common mechanism involves formation of bromoniumion

Brt CH3CH2CHCH3 + Br-Bra

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sa

cis

shut

St CH3 CH-CACH3 Bro

completion of Addition:

BV

CHaut-CHCH2 CH3CH - CACH3

Br when soment acts as nucleophile (excess water):

Br

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Br

CH3CH3 - CHCH3

By -


What are the cyclic compounds?



BrĮ (H2CH - CH CH 3 Don't forget about the age old question of biology exam 2

H2O:

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ht

H2O

H2O remones potont

product

Br Br

H3

CH3CH - CH CH3 + H30T + Br CH3CH CHCH3

It - o

OH -opposite side substitusion:

bromide son acrina as

vs *Stereoselective ANTI- Adaition

nucleopnice aonares e- pair

To carbon at opposire face

to bond that breaks EX: Br

Br

Inversion configuration) Hlinic - cuilt

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OXY MERCURATION - alkenes react w/ Hg CO Ac/z OH add to double bond

to give products in wr

OAC and

THE

CH3CH2CH2CH-CH=CH2tAcO-Ha-OA+H-OH


What is the definition of meso compound?



CH3CH2CH2CH2-CH2-CH2

H26

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Off Hgot *Hadac goes to c

+HOAC of double bond wl fewer alky substituents +OH goes to c wl more If you want to learn more check out which of the following statements is true about a hurricane as it makes landfall?

Hg - OAC R-CH=CH2 + Hg (OAC)2 → R-CH-CH2 -OAC

MERLURINIUMION -Also reacts wl solvent water

Hg - OAC

(Hot Otel HG-OAC

R-CH - CH2 R-CH-CH R-CH-CH2

OHZ

OH 얘

when theated WI NaBty in

presence of NaOH,

this is replaced 1. Hgd Ac), H2O

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2. NaBtu/Naolt

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OH

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*Stereospecific and addition*

- Not steres selective, but regioselective HYDROBORATION - Anti Markomnikov -OH bonds TDC wl tewer alkyl substituent -BH3 bonds to alkere so boron is bonaed To cwl femer alky I

surostituents and it to ac wl more

(CH3)2C =CH2 + H-BHz (CH3)2C - CH2

H

Bitz

-

After 3ra Aaclition:

В+ctz-CCCH3)2)

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1 group a aconexa -products can then be converted

Then be converted to alcohols wl H2O2 + NaOH

to alconals we Bt CH2-C(CH3)2 + 3H2O2 + OH 3 (CH3)2C- CH2-OH + B (OH)

*replacement ce boron

by ott group *Stereo specific SYN Addition* -occurs w/ retention OZONOLYSIS - ozonice breaks cacbona

CH2Cl2 Нас с =сH +

H3C-HC-CH-CH3 oo H3CHC CH-CH3

O

ozonide cyclic e flow to form aldenyale - addenycle oxide

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CH-CH (H3C CH3

H3C FREE RADICAL ADDITION + FISH HOOK -Homolytic Process: e's move in unpained way We also discuss several other topics like molecular basis of inheritance notes

Her Hot:Br. Free radical chain rxn: (1) Initiation source of tree radicals (2) Propogation (3) Terminarion

Inimation - text butyl peroxicle frequently used

Soul (CH3)- Ö-o E(+13)c 2(CH 3 3C -0. 2nd initiation step WIHBr:

(CH3)3 C-0 H-Br (CH3)3C-0-H+ Bri Propogarion- radicals react wi non radicals to give other radicals

grudyson R-CHECH-

R R -CH-CH-R

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radicals react Br. •Br

to give non radical products

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PEROXIDE EFFECT - WBW when traces of peroxide are present, regioselectivity of HBr is reversed

benzy CH3 CH2 CH = CH2 +H-Br pernicie CH3CH2CH2 CH2 CH2 - Br

*FASTER* Free radical mechanism = basis for understanding peroxide effect

H3C

0 H3 C -

6 (Hz Soup H3C •Br

It3cbr

Terriam Free radical

more stable - Steric Affed when crum. van is affected by van der waa's repuisions ENANTIOMERS SCHIRALITY - Stereoisomers: same connectivity but diff arangements of atoms in space - Enantiomers: molecules congruent to their minor images

Molecules that can exist as enansiomers = CHIRAL no - Asymmetric carbon: c to which 4 ciff groups are bound

molecule containing exactry i asymmetric c is chiral stened center: arrom at which interchanging of a groups gives Stereoisomer * molecule that has plane of symmetry is achival Nomenclature cf Enantiomers: 1) identify asymmetric C+ its y aiff groups z) Assign priorities to groups 3) view moccues from asymmetric C To lowest priority Don't forget about the age old question of odu final exam

4). I prioriñies cecrease in clockwise direcrion → Rconfigurarion, counterclockw

ise contiquration -indivianal enantiomers are of chival moucules are oprically acrive dysour

& Enansiomers rotare equal arts of light in opposite directions + Dexroat Dextrorotang:rotes rotates lignt clockwise

Leverotutory: rotates right counterclockwise A Enantiomenic Excess =010 malor enantiomer - Minor enansiomerk - Racemic Mixture: contains equal amb af z enantiomers

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-ness com pound: Aomval compound that has chiral diastereomers

Has atleast 2 stereocenters H3 C CH3 H CH3

achival

*Bom ar arinat but са с

nother has chiras

Stered somers or arummernic H3C H

C's 7 NOT MESO cis-2-burene If you want to learn more check out precalculus chapter 5 study guide

Trans--butene -reso compound is only possible when a more wire wi 2+ asummericcis can be divided into halves wi same connectivity can be al

CH3

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Must – – 1 – – nave opposite - CH - olt configur

CH3 CYCLIC COMPOUNDS monocyclic compound-contains single ving We also discuss several other topics like bio 102 exam 1

cyclone dane is the stablest Chair conformation:

HCBA W-axial

* CHAIR INTERCONVERSIONS

Turn axial Into enunrial & vice versa

but down remains H it

it t it down up remains up * Eauitonal conf. w more stable ble it has no vanaer waals repulsions -Boat conformations very unstable ane to rander waals Teclipsed tis

undergoes sight dantomation town

ation (Twist boat conf.) Half chair rotasion

BOAT

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Boat - Ennecope conformation: "puckerea" undergoes rapid interconversions in

which cis alternates as the point of the envelope - Angle strain excess energy reflected in a heat of formation / bora

angles denare from ideal values) sty Bicuplic compounds : 2 ungs snare 2+ common atoms Spirocyclic : 2 rings share a common arom

Eleanphilir.

S

Mawl Tewer Group (modified Marromnivors

olhes donarion of a

bicyclo [4.3.0]

bicyclo [2.2.17

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Spiro (4.4] nonane

Spirocyclic Bicyclic Stud Bridge head caroons: aroms which a rings are joinea

Fused ugclic: 2 briagehead carbons are adjacent Braged Bicycic & bridgehead carbons are not adjacent

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non agail activitie rates wi er and a ve their

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FUSED BRIDGED

o one carbon briage

=) bicyclo [3.2.1) octune 3 carbon briage 2 carbon

bridge z rings can be fuced in cis or trans awangement 2 when vings are small, only is fusion is obsemed due to vina strain

3 in large vings, trans is more stable bic na 1,3-diaxial interactions are minimized

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