[PDF] [PDF] 141 Introduction to Ethers 141 Introduction to Ethers 142 Naming

[PDF] Naming Ethers and Thiols (Naming and Properties)

Cyclic ethers (heterocyclic compounds) are often given common names DO NOT memorize IUPAC Names for Ethers The shorter alkyl group and the oxygen are  

[PDF] 141 Introduction to Ethers 141 Introduction to Ethers 142 Naming

Practice with CONCEPTUAL CHECKPOINT 14 4 14 4 Crown Ethers Copyright 2012 John Wiley Sons, Inc Klein, Organic Chemistry 1e

[PDF] Nomenclature - Alcohols + Ethers

Cyclic ethers are named as oxacycloalkanes with the oxygen being at position 1 of the chain Simple ethers may be given common names as alkyl alkyl ethers where the alkyl groups attached to the oxygen are listed in alphabetical order

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Practice 8-4 Write a chemical equation showing reactant and product for each of the following If no reaction occurs, write “NR” a) oxidation of 2-methyl-1- 

[PDF] Chapter 3 Alcohols, Phenols, and Ethers - Angelo State University

Chapter Objectives: • Learn to recognize the alcohol, phenol, and ether functional groups • Learn the IUPAC system for naming alcohols, phenols, and ethers

[PDF] Nomenclature

It provides an unambiguous structure • Official IUPAC naming recommendations are not always followed in practice, and the common or trivial name may be

[PDF] Chem 124 PAL Worksheet Alcohols Ethers Phenols Page 1 Write

Alcohols Ethers Phenols Page 1 Write out the answers on separate sheets of paper 1 Give the IUPAC name for the following molecules 2 Write the structure  

[PDF] Unit One Part 2: naming and functional groups

6-(hydroxymethyl)-tetrahydro- 2H-pyran-2,3,4,5-tetraol glucose sugar I guess Page 14 Functional groups: phenols and ethers gjr-–-

[PDF] NOMENCLATURE IN ORGANIC CHEMISTRY

In the naming of ethers as alkyloxy derivatives of alkanes, it is general practice to shorten the names of compounds containing four or less carbons to alkoxy 

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•Anethergroupincludesan oxygenatomthatisbonded toTWO-Rgroups:

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Klein, Organic Chemistry 1e14 -1

O

14.1IntroductiontoEthers

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Klein, Organic Chemistry 1e14 -2

•Commonnamesareusedfrequently:

1.Nameeach-Rgroup.

2.Arrangethemalphabetically.

3.Endwiththeword"ether."

14.2NamingEthers

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Klein, Organic Chemistry 1e14 -3

14.2NamingEthers

Copyright2012JohnWiley&Sons,Inc.

Klein, Organic Chemistry 1e14 -4•Namethefollowingmolecule.

14.2NamingEthers

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Klein, Organic Chemistry 1e14 -5

waterandinalcohols. •Istheoxygenatominanethersp 3 ,sp 2 ,orsp hybridized?

14.3StructureandPropertiesof

Ethers

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Klein, Organic Chemistry 1e14 -6

boilingpoints. canhave? ether canhave?

14.3StructureandPropertiesof

Ethers

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Klein, Organic Chemistry 1e14 -7

boilingpoints. elevatedsimilartoalcohols? •WHYorWHYnot?

14.3StructureandPropertiesof

Ethers

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Klein, Organic Chemistry 1e14 -8

intermolecularattractions. -Trend1: -Trend2:

14.3StructureandPropertiesof

Ethers

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Klein, Organic Chemistry 1e14 -9

afterthereactioniscomplete. partiallychargedtransitionstates.HOW? inmanyreactions?

14.3StructureandPropertiesof

Ethers

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Klein, Organic Chemistry 1e14 -10

stabilizedbyethersolvents. reactions. •Giveanotherreasonwhyanethermakesa goodsolventinthisreaction.

14.4CrownEthers

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Klein, Organic Chemistry 1e14 -11

strongattractionstometalatoms.WHY? •WhyaretheycalledCROWNethers?

14.4CrownEthers

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Klein, Organic Chemistry 1e14 -12

toformastrongattraction. •18ͲcrownͲ6fitsaK ionjustright.

14.4CrownEthers

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Klein, Organic Chemistry 1e14 -13

solvents.WHY? inlowpolaritysolvents.WHY? polarityorganic substrates.

14.4CrownEthers

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Klein, Organic Chemistry 1e14 -14

•TheF ionbelowisreadytoreactbecausetheK ionis sequesteredbythecrownether. isminiscule.

14.4CrownEthers

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Klein, Organic Chemistry 1e14 -15

•Generally,theF ionisnotusedasanucleophile solvent,theF ionissolubleenoughthatitcanreadily attackanelectrophile.

14.4CrownEthers

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Klein, Organic Chemistry 1e14 -16

14.4CrownEthers

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Klein, Organic Chemistry 1e14 -17

catalyzeddehydrationofethanol. •Howisitadehydration?

14.5PreparationofEthers

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Klein, Organic Chemistry 1e14 -18

manyasymmetricalethers. •Whathappenstothehalide?

14.5PreparationofEthers

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Klein, Organic Chemistry 1e14 -19

manyasymmetricalethers. secondary,ortertiaryalkylhalides?

14.5PreparationofEthers

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Klein, Organic Chemistry 1e14 -20

themethylside.WHY? •PracticewithSKILLBUILDER14.2.

14.5PreparationofEthers

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Klein, Organic Chemistry 1e14 -21

followingmolecule.

14.5PreparationofEthers

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Klein, Organic Chemistry 1e14 -22

•Istheadditionsynoranti?

14.5PreparationofEthers

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Klein, Organic Chemistry 1e14 -23

usedtosynthesizeethers. •Istheadditionsynoranti?

14.5PreparationofEthers

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Klein, Organic Chemistry 1e14 -24

ethersaregenerallyunreactive. •Considertheetherbelow. •Wherearethemostreactivesites? nucleophile,electrophile,etc.?

14.6ReactionsofEthers

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Klein, Organic Chemistry 1e14 -25

14.6ReactionsofEthers

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Klein, Organic Chemistry 1e14 -26

forthefollowingacidͲpromotedcleavage.

14.6ReactionsofEthers

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Klein, Organic Chemistry 1e14 -27

effective. cleavage. strengthofthehalidenucleophiles. thanacidͲcatalyzed?

14.6ReactionsofEthers

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Klein, Organic Chemistry 1e14 -28

completemechanism.

14.6ReactionsofEthers

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Klein, Organic Chemistry 1e14 -29

autooxidation. hydroperoxidesbeforetheyareused. mechanism.

14.6ReactionsofEthers

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Klein, Organic Chemistry 1e14 -30

14.6ReactionsofEthers

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Klein, Organic Chemistry 1e14 -31

propagationsteps:

14.6ReactionsofEthers

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Klein, Organic Chemistry 1e14 -32

parentnameofthemolecule. •Oxiranesarealsoknownasepoxides. reactive?WHY?

14.7NamingEpoxides

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Klein, Organic Chemistry 1e14 -33

•Anepoxidecanhaveupto4-Rgroups. commonlyinnature.

14.7NamingEpoxides

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Klein, Organic Chemistry 1e14 -34

givenasitslocants.

2.Oxiraneisusedastheparentname.

14.7NamingEpoxides

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Klein, Organic Chemistry 1e14 -35

14.7NamingEpoxides

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Klein, Organic Chemistry 1e14 -36

whenanalkeneistreatedwithaperoxyacid.

14.8PreparationofEpoxides

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Klein, Organic Chemistry 1e14 -37

14.8PreparationofEpoxides

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Klein, Organic Chemistry 1e14 -38

•Whatisahalohydrin? reactioncanoccur.

14.8PreparationofEpoxides

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Klein, Organic Chemistry 1e14 -39

14.8PreparationofEpoxides

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Klein, Organic Chemistry 1e14 -40

•PracticewithSKILLBUILDER14.3.

14.8PreparationofEpoxides

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Klein, Organic Chemistry 1e14 -41

NOTenantioselective.

•Drawtheproducts.

14.9EnantioselectiveEpoxidation

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Klein, Organic Chemistry 1e14 -42

flatalkenecanreactoneitherface.

14.9EnantioselectiveEpoxidation

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Klein, Organic Chemistry 1e14 -43

thecatalyst)inareactionmustbechiral. anallylicalcohol.

14.9EnantioselectiveEpoxidation

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Klein, Organic Chemistry 1e14 -44

ischosen.Notethepositionofthe-OHgroup. •PracticewithCONCEPTUALCHECKPOINT

14.16.

14.9EnantioselectiveEpoxidation

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Klein, Organic Chemistry 1e14 -45

greatsyntheticutilityasintermediates. epoxidetoalterthecarbonskeleton.

14.10RingͲopeningofEpoxides

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Klein, Organic Chemistry 1e14 -46

favored,andexplainWHY.

14.10RingͲopeningofEpoxides

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Klein, Organic Chemistry 1e14 -47

potentialenergymakingitmorereactive.

14.10RingͲopeningofEpoxides

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Klein, Organic Chemistry 1e14 -48

thermodynamicallyfavored.WHY?

14.10RingͲopeningofEpoxides

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Klein, Organic Chemistry 1e14 -49

nucleophilesaswell. considered.

14.10RingͲopeningofEpoxides

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Klein, Organic Chemistry 1e14 -50

N

2,predictthe

outcomeofthefollowingreactions. WHY. •PracticewithSKILLBUILDER14.4.

14.10RingͲopeningofEpoxides

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Klein, Organic Chemistry 1e14 -51

O

14.10RingͲopeningofEpoxides

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Klein, Organic Chemistry 1e14 -52

underacidicconditions. •Antifreeze(ethyleneglycol)ismade industriallybythismethod.

14.10RingͲopeningofEpoxides

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Klein, Organic Chemistry 1e14 -53

observations.

14.10RingͲopeningofEpoxides

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Klein, Organic Chemistry 1e14 -54

S N 1orS N 2? likelyS N 1orS N 2?

14.10RingͲopeningofEpoxides

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Klein, Organic Chemistry 1e14 -55

•Whenthenucleophileattacksatertiary centeroftheepoxide,theintermediateit attackstakesonsomecarbocationcharacter (S N

1),butnotcompletely.

•PracticewithSKILLBUILDER14.5.

14.10RingͲopeningofEpoxides

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Klein, Organic Chemistry 1e14 -56

the-OHgroupinalcohols. "thiol" ratherthan"ol." •Notethatthe"e" ofbutaneisnotdroppedin thenameof thethiol.

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -57

•Thiolsarealsoknownasmercaptans. groupratherthanaspartoftheparentchain. complexmercury. mercurypoisoning.WHY?Draw itsstructure.

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -58

gasleakscanbedetected. •Thehydrosulfideion(HS )isastrongnucleophileanda weakbase. •HS promotesS N

2ratherthanE2.

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -59

drawacompletemechanism.

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -60

•ThiolshaveapK a ofabout10.5. •RecallthatwaterhasapK a of15.7. productsorreactantsanddrawthemechanism. •Thiolatesareexcellentnucleophiles.

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -61

thiolate ion •Onceathiolateforms,itcanattackBr 2 toproducea disulfide. •Howdoestheoxidationnumberchange?

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -62

Proposeamechanism.

about53kcal/mol.WHYisthatsignificant?

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -63

THIOETHERS.

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -64

athiolateonanalkylhalide. •Howarethiolatesgenerallyprepared?

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -65

•Sulfidesundergoanumberofreactions:

1.Attackonanalkylhalide:

addanalkylgrouptoavarietyofnucleophiles.

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -66

•Sulfidesundergoanumberofreactions:

2.Sulfidescanalsobeoxidized.

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -67

•Sulfidesundergoanumberofreactions:

2.Sulfidescanalsobeoxidized.

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -68

character. contributor,andWHY?

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -69

reducingagents.

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -70

reactionsequencebelow. productabove.

14.11ThiolsandSulfides

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Klein, Organic Chemistry 1e14 -71

Br HS

1) NaOH

2) adjacentcarbons. •PracticewithSKILLBUILDER14.6.

14.12SyntheticStrategiesInvolving

Epoxides

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Klein, Organic Chemistry 1e14 -72

carbonskeletoncanbemodified.

14.12SyntheticStrategiesInvolving

Epoxides

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Klein, Organic Chemistry 1e14 -73

•Recallthatacarbonylcanbe usedtoinstallaonecarbon chainbetweenanRgroupand anOHgroup. betweenanRgroupandanOHgroup.

14.12SyntheticStrategiesInvolving

Epoxides

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Klein, Organic Chemistry 1e14 -74

•PracticewithSKILLBUILDER14.7.

14.12SyntheticStrategiesInvolving

Epoxides

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Klein, Organic Chemistry 1e14 -75

quotesdbs_dbs14.pdfusesText_20