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Sources Structure, Nomenclature, Properties Acidity and Basicity Rx with active metals Conversion to R-X, inorganic acid halides Rxs with HX S N 1/S N 2, sulfonates Dehydration of alcohols Oxidation of 1 o and 2 o alcohols Oxidation of glycols

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alcohols thiols ethers
Sources

Structure, Nomenclature, Properties

Acidity and Basicity

Rx with active metals

Conversion to R-X, inorganic acid halides

Rxs with HX SN1/SN2, sulfonates

Dehydration of alcohols

Oxidation of 1o and 2o alcohols

Oxidation of glycols

[Pinacol & Thiols/Sulfur chemistry - skip]

Chapter 11

Chapter 10

Alcohols & Thiols &Ethers

6, 31, ss34

slide2

Chapter 10

synthesis

sources

nomenclature

(alcohol & ethers)

properties

reactions

acid base

active metal

substitution

oxidation

slide4

Chapter 10

synthesis

sources

nomenclature

(alcohol & ethers)

properties

reactions

acid base

active metal

substitution

oxidation

nomenclature alcohols ethers
IUPAC names – alcohol sp3C-OH

-longest chain that contains the -OH = root

-OH gp lowest number

- suffix -e to -ol

Nomenclature alcohols & ethers

ether R-O-R’ sp3C, sp2C, spC in R & R’ bonded to O

-always subsituent

- #-prefix, alkoxy

(special ethers #,#-epoxy)

1-ethoxy-2-butanol

slide6

Epoxides - 11 - special ethers

Nomenclature - #,#-epoxy (substituent) oroxirane

ether acetylene alcohol

#,#-epoxy-#-pentyn-#-ol

(4S)-4,5-epoxy-2-pentyn-1-ol

nomenclature alcohols
IUPAC names

Longest chain that contains the -OH = root

Give -OH group lowest number

Change suffix -e to -ol

(S)-2-methyl-1-butanol

Nomenclature-Alcohols
slide8

H

C

3

oxygen sp3

Structure - Alcohols

  • Alcohol functional group:
  • -OHgroup bonded to an sp3 hybridized carbon
    • bond angles ~ 109.5°

H

H

H

C

O

slide9

etc.

R

H

R

H

O

O

O

H

R

R

H

O

Physical Properties

Hydrogen bonding: H bonded to an electronegative atom (F, O, or N)

Hydrogen bond weak (~ 5 kcal/mol)

physical properties
ethanol & dimethyl ether - constitutional isomers but weak hydrogen bonds have dramatic effects:Physical Properties

hydrogen bonds no hydrogen bonds

slide11

Reactions

alcohols: acid

base

indirect substitution

indirect-elimination

active metals

oxidation

ethers: base

indirect substitution

indirect-elimination

epoxides: substitution, indirect& direct

acidity of alcohols
weak acidsAcidity of Alcohols

conjugate basesstrong

slide14

Acidity of Alcohols

Acidity  on: stabilization and solvation

electron donation

destabilize alkoxides

Steric BULK

decreases solvation

slide15
Alcohols + Li, Na, K (active metals)

form metalalkoxides

alcohols rx with metals

metal alkoxide

sodium methoxide

slide16

rx with metals

sodium cyclohexoxide

slide17

basicity of alcohols/ethers

weak Lewis base

(water-like)

oxonium ion

R = H or alkyl

slide18

Alcohols/Ethers indirect Substitution (with HX)

3° alcohols (ethers) react very rapidly with HCl, HBr, HI.

1°alcohols/ethers are unreactive under these conditions

R = H or alkyl

slide19
2° alcohols + HBr (or HI )

indirect Substitution (with HX)

racemization, rearrangement, olefins

slide20

-H+

+X-

+X-

[-HOR]

good leaving

group

2o or 3o ROH/ROR’ with HX - SN1

racemization, rearrangement, olefins

R = H or alkyl

slide23

2nd ROH to RBr

3rd ROH to RBr

indirect Substitution (with PBr3)

slide24

indirect Substitution

R= H, alkyl

R’= H, alkyl; X= Br, I

alkyl sulfonates sulfonate ester

S

S

DMF

R

S

alkyl sulfonates (sulfonate ester)

good leaving group for Sn2 rx

slide27

rx:

alkyl sulfonates

prep:

slide28

rx:

alkyl sulfonates

prep:

slide29

2° alcohols (ethers)

3° alcohols (ethers)

dehydration of ROH/[-HOR’] of ROR’

1° alcohols (ethers) with H2SO4 or H3PO4

R = H or alkyl

slide31

Chapter 10

synthesis

sources

nomenclature

properties

reactions

acid base

active metal

substitution

oxidation

oxidation 1 roh
Pyridinium chlorochromate (PCC):

pyridine + CrO3 [Cr(VI)] + HCl

Oxidation: 1° ROH

PCC converts 1° alcohols to aldehydes

and 2o alcohols to ketones

slide34

Oxidation

aldehyde

acid

ketone

NR (no reaction)

slide35

+

-elimination of H and chromate

slide36

Oxidation: 1° ROH

hydrate

hydrate

slide37

K2Cr2O7

and many

other reagents

Oxidation 1o and 2o ROH

slide40

How does one

make butanal

from 1-bromobutane?

slide41

What else can

be made using the

chemistry of chapters

3, 6, 7, 8, 9, 10, 11 & “15”?

slide43

Chapter 10

Chapter 11/15

synthesis

synthesis

sources

nomenclature

properties

reactions

acid base

active metal

substitution

oxidation