Transcript
Page 1: Chapter 04 Alcohols and Alkyl Halides - NDSUcook.chem.ndsu.nodak.edu/chem341/wp-content/uploads/2012/02/Che… · Chapter 04 Alcohols and Alkyl Halides part 01 CHEM 341: ... CFCs

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©2012 Gregory R Cook

Chapter 04Alcohols and Alkyl Halides

part 01

CHEM 341: Spring 2012

Prof. Greg Cook

cook.chem.ndsu.nodak.edu/chem341

Wednesday, February 8, 12

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Functional Groups

• A functional group is a structural feature in a molecule that has characteristic reactivity.

• A functional group has similar behavior in every molecule that contains it.

2

Carbon-Carbon Multiple Bonds

Alkenes - double bonds

CH2 CH2

Alkynes - triple bonds

C C

Arenes - aromatic rings

Carbon-Other atom Single Bonds

OH

Alcohols

Br

Hallides

NH2

Amines

OCH3

Ethers

SH

Thiols

SCH3

Sulfides

Carbon-Oxygen Double Bonds (Carbonyls)

H

AldehydeO

KetoneO

OH

AcidO

OCH3

EsterO

NH2

AmideO

Cl

Acid HalideO

H H

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Functional Groups

• A functional group is a structural feature in a molecule that has characteristic reactivity.

• A functional group has similar behavior in every molecule that contains it.

2

Carbon-Carbon Multiple Bonds

Alkenes - double bonds

CH2 CH2

Alkynes - triple bonds

C C

Arenes - aromatic rings

Carbon-Other atom Single Bonds

OH

Alcohols

Br

Hallides

NH2

Amines

OCH3

Ethers

SH

Thiols

SCH3

Sulfides

Carbon-Oxygen Double Bonds (Carbonyls)

H

AldehydeO

KetoneO

OH

AcidO

OCH3

EsterO

NH2

AmideO

Cl

Acid HalideO

H HR OH R Xalcohols alkyl halides

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Reactions of Functional Groups

3

H XR OH + H OHR X +

OHR X + R OH + X

X XR H + H XR X +

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General Reaction Classes

• Addition Reactions - two or more molecules combine to form a new product

• Elimination Reactions - a molecule breaks apart into two or more molecules

• Substitution Reactions - part of a molecule is substituted for another group

• Rearrangement Reactions - A molecule does not gain or lose atoms, but reorganizes its bonds or groups. Also called isomerization.

4

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General Reaction Classes

• Addition Reactions

• Elimination Reactions

• Substitution Reactions

• Rearrangement Reactions

5

A + B C C CH

H

H

H+ H2 cat.

C CH

HHH

H

H

CA B + BA C + H3C Cl + OH H3C OH + Cl

BA heatO O

A + BC cat.OH

H

+ HOH

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• Organic halogen compounds are found in many places from common solvents for chemistry and industry, to refrigerants (largely banned for their ozone destruction properties) and natural products.

Alkyl Halides

6

CH2Cl2CHCl3CH2Cl-CH2Cl

commonsolvents

CFCs(chlorofluorocarbons)

CF2Cl2

natural products(epibatidine)

NH

N

Cl

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• Alkyl halides are often named using common naming (functional class) considering the alkyl group as a substituent on the halide.

Alkyl Halide Nomenclature

7

methyl bromide

H3C BrI

cyclopentyl iodide 1-methylpropyl chloride

Cl

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• IUPAC naming is best using the carbon chain as the parent and the halogen as a halo- substituent

Alkyl Halide Nomenclature

8

bromomethane

H3C BrI

iodocyclopentane 2-chlorobutane

Cl

Br Br

4-bromo-2-methylhexane 2-bromo-4-methylhexane

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• Alcohols are often named using common naming (functional class) considering the alkyl group as a substituent on the OH functional group.

Alcohols

9

methyl alcohol

H3C OHOH

cyclopentyl alcohol isopropyl alcohol

OH

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• IUPAC naming is best using the carbon chain as the parent and replacing the -ane ending with -anol

• note: alcohols outrank alkyl substituents

Alcohol Nomenclature

10

methanol

H3C OHOH

cyclopentanol 2-propanol

OH

OH OH

5-methyl-3-hexanol 4-methyl-2-hexanol

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• Alcohols and alkyl halides are classified according to the degree of alkyl substituion on the carbon the functional group is attached

Classes of Alkyl Halides and Alcohols

11

OH

1-propanola primary alcohol

2-chloro-2-methylbutanea tertiary halide (chloride)

Cl OH

trans-3-methylcyclopentanola secondary alcohol

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• Reactivity is dominated by the polarity of the C-X bond

Properties of Alkyl Halides

12

fluoromethane CH3-F 1.85 1.39 108

chloromethane CH3-Cl 1.87 1.78 84

bromomethane CH3-Br 1.81 1.93 70

iodomethane CH3-I 1.62 2.14 56

diopole moment(Debyes)

bond length(Å)

bond strength(kcal/mol)

µ = 1.9 D

C Cl

H

H

H

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• Acohols are polar but have other reactive features

Properties of Alcohol

13

weakly acidic

RO

H

weakly basic

µ = 1.7 D

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Boiling Points of Halides and Alcohol

14

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Intermolecular Forces

15

• Induced dipole/induced dipole (London forces, van der Waals attraction)

• Dipole/induced dipole forces

• Diplole/Dipole forces

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Intermolecular Forces

16

bp -24 °C

RO

H

µ = 1.7 Dµ = 1.9 D

C Cl

H

H

H

bp 65 °C

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• At about 5 kcal/mol, H-bonds are weaker than covalent bonds but stronger than many other intermolecular forces

Hydrogen Bonding

17

RO

H

δ−

δ+

R

O Hδ− δ+

hydrogenbond

R

OHδ−δ+

hydrogenbond

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• Polarizability - the ability to distort (polarize) electrons in a bond

Polarizability

18

chloromethanebp -24 °C

C Cl

HH

H

C Cl

ClH

H

C Cl

ClCl

H

C Cl

ClCl

Cl

dichloromethanebp 40 °C

trichloromethanebp 61 °C

tetrachloromethanebp 77 °C

fluroethanebp -32 °C

C F

HH

C

1,1-difluoroethanebp -25 °C

1,1,1-trifluoroethanebp -47 °C

hexafluoroethanebp -77 °C

HH

H

C F

FH

CH

H

H

C F

FF

CH

H

H

C F

FF

CF

F

F

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• Alcohols are similar to water but the solubility decreases as the hydrocarbon chain increases

Alcohol Solubility

19

CH3 OH

AlcoholSolubility in Water(g/100 g H2O)

CH3CH2 OH

OH

OH

OH

OH

OH

OH

OH

miscible

miscible

miscible

9

2.7

0.6

0.18

0.054

insoluble

Carbons

1

2

3

4

5

6

7

8

10

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• Alkyl halides are hydrophobic and insoluble in water.

• Fluorides and chlorides are less dense than water, bromides and iodides more dense

• But, if it has more than one chlorine, they are more dense

Alkyl Halide Solubility and Density

20

less dense

C Cl

HH

H

C Cl

ClH

H

C Cl

ClCl

H

C Cl

ClCl

Cl

more dense more dense more dense

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• from alcohols by a substitution reaction

Preparation of Alkyl Halides

21

H XR OH + H OHR X +

Alkyl Alcohol Hydrogen Halide Alkyl Halide Water

reactivity

H F H Cl H Br H I< < <

reactivity

<H CH

HOH < R C

H

HOH R C

H

ROH R C

R

ROH< <

methyl primary secondary tertiary

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Preparation of Alkyl Halides

22

OH

H Br

80-100°C

Br

OHH Br

25°C

Br

H Br

120°COH Br

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Preparation of Alkyl Halides

23

• Can use a combination of halide salt and other Brønsted acids

heatOH Br

NaBr H2SO4

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Preparation of Alkyl Halides

23

• Can use a combination of halide salt and other Brønsted acids

heatOH Br

NaBr H2SO4

• How does the reaction work?

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Preparation of Alkyl Halides

23

• Can use a combination of halide salt and other Brønsted acids

heatOH Br

NaBr H2SO4

• How does the reaction work?

• A reaction mechanism is a detailed step by step description of a chemical transformation showing all elementary steps and intermediates

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Thermodynamics

24

• The change in energy of a reaction from one side to the other

• If ΔG° is negative (energy released) the reaction is downhill (exothermic).

• ΔG° is positive (energy absorbed) the reaction is uphill (endothermic)

ΔG° = -RT ln Keq ΔG° = ΔH° - TΔS°

Gibb's Free Energytotal change in energy in the system from reactants to products

Enthalpy"Heat of Reaction" total change in the bonding energies of a reaction

EntropyAmount of freedom (or disorder). Greater entropy means more freedom, less entropy means more restricted

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Thermodynamics

25

• The difference in energy is a reflection in the change of the bonds (enthalpy)

• Bond Dissociation Energy - the energy required to homolytically cleave a bond

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Thermodynamics of Alcohol Substitution

26

• Thermodynamics only deals with the energy of reactans and products (equilibrium). It says nothing about the path between them.

Bonds Broken (energy put in)

C-O bond 358 kJ/mol366 kJ/molH-Br bond

total energyput in

ΔH° = 724 - 750 = - 26

H BrR OH + H OHR Br +

Bonds Formed (energy released)

C-Br bond 285 kJ/mol465 kJ/molH-O bond

total energyreleased

724 kJ/mol 750 kJ/mol

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Kinetics

27

E

reaction progress

transition state ‡

ΔG°A

B

energybarrierto climb

• Kinetics deals with the pathway and describes the rate of reactions - higher energy paths are slower. We can visually map the energy on a reaction potential energy diagram.

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Kinetics

28

E

reaction progress

transition state ‡

ΔG°

transition state ‡slowest stephighest energy hill

A

B

C

intermediate

• A multistep reaction path

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• Activation Energy - the energy required to overcome the energy barrier

• Rate Determining Step - the slowest step in a reaction mechanism - the step with the highest energy barrier

• Transition State - the structure of molecules at the highest energy point of each energy barrier.

• The structure of the TS will most closely resemble the nearest intermediate - Hammond’s Postulate

Some Terms

29

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Mechanism for Alcohol reaction with HX

30

H XR OH + H OHR X +

Alkyl Alcohol Hydrogen Halide Alkyl Halide Water

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Mechanism for Alcohol reaction with HX

31

H BrR OH + R O

H

H

Br+

Step 1

fast

bimolecular reaction

R +

Step 2

slow

unimolecular reaction

R O

H

H

H OH

R Br

Step 3

fast

bimolecular reaction

Br+R

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Step 1 - Protonation of Alcohol

32

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Step 2 - Dissociation of Water

33

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Step 3 - Addition of Halide

34

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Overall Reaction Energy Diagram

35

• SN1 reaction mechanism

Substitution Nucleophilic Unimolecular

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