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CH3b Isomers

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Isomerism • Molecules which have the same molecular formula, but differ in the arrangement of their atoms, are called isomers. • Constitutional (or structural) isomers differ in their bonding sequence. • Stereoisomers differ only in the arrangement of the atoms in space. =>
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Page 1: CH3b Isomers

Isomerism

• Molecules which have the same molecular formula, but differ in the arrangement of their atoms, are called isomers.

• Constitutional (or structural) isomers differ in their bonding sequence.

• Stereoisomers differ only in the arrangement of the atoms in space. =>

Page 2: CH3b Isomers

IsomersIsomers

StereoisomersStereoisomersconnectivity =connectivity =

orientationorientation≠≠

ConstitutionalConstitutionalstructural structural

connectivity connectivity ≠≠

DiastereomersDiastereomersnot mirror images

EnantiomersEnantiomersNon-superimposable mirror image

Page 3: CH3b Isomers

Structural Isomers

CH3 O CH3 and CH3 CH2 OH

CH3

CH3and

=>

Page 4: CH3b Isomers

ethane ethane

CC22HH6 6 oror CHCH33CHCH33

alkanes: propane (CHalkanes: propane (CH33CHCH22CHCH33))

H C

H

H

C H

H

H

C H

H

H

Page 5: CH3b Isomers

propane (Cpropane (C33HH88))

H C

H

H

C

H

H

C H

H

H

alkanes: CHalkanes: CH33CHCH22CHCH33

Page 6: CH3b Isomers

propane (Cpropane (C33HH88))

H C

H

H

C

H

H

C H

H

H

alkanes: CHalkanes: CH33CHCH22CHCH33

Page 7: CH3b Isomers

propane (Cpropane (C33HH88))

H C

H

H

C

H

H

C H

H

H

C H

H

H

C H

H

Horor

alkanes: propanealkanes: propane

Page 8: CH3b Isomers

butane (Cbutane (C44HH1010))H C

H

H

C

H

H

C H

H

H

propane propane (C(C33HH88))

H C

H

H

C

H

H

C C

H

H

H

H

H

H C

H

H

C

C

H

C H

H

H

H H

H

alkane isomers:alkane isomers: How many How many CC55HH1010 isomers? isomers?

Page 9: CH3b Isomers

butane (Cbutane (C44HH1010))

H C

H

H

C

H

H

C C

H

H

H

H

H

H C

H

H

C

C

H

C H

H

H

H H

H

alkane isomers:alkane isomers: How many How many CC55HH1010 isomers? isomers?

Page 10: CH3b Isomers

butane (Cbutane (C44HH1010))

H C

H

H

C

H

H

C C

H

H

H

H

H

H C

H

H

C

C

H

C H

H

H

H H

H

alkane isomers:alkane isomers: How many How many CC55HH1212 isomers? isomers?

C C C C C

H

H

H

H

H

H

H

H

H

H

H

H

Page 11: CH3b Isomers

How many CHow many C55HH12 12

isomers?isomers?

these two structures these two structures are identicalare identical

bond line bond line structures:structures:

Page 12: CH3b Isomers

alkane isomers:alkane isomers: How many CHow many C55HH12 12

isomers?isomers?

these two structures these two structures are identicalare identical

Page 13: CH3b Isomers

alkane isomers:alkane isomers: How many CHow many C55HH12 12

isomers?isomers?

these two structures these two structures are identicalare identical

Page 14: CH3b Isomers

alkane isomers:alkane isomers: How many CHow many C55HH12 12

isomers?isomers?

Page 15: CH3b Isomers

Butane = CButane = C44HH1010, CH, CH33CHCH22CHCH22CHCH33

HH

H H

H HH H

HH

C C

H

H

H

H

H

C

H

H

C

H

H

H

Page 16: CH3b Isomers

Butane, bond rotationsButane, bond rotations

Page 17: CH3b Isomers

rotations about single rotations about single bonds are very fast.bonds are very fast.

Butane, bond rotationsButane, bond rotations

Page 18: CH3b Isomers

= butane= butane

Butane, bond rotationsButane, bond rotations

Page 19: CH3b Isomers

==

Butane, bond rotationsButane, bond rotations

Page 20: CH3b Isomers

Isomers of CIsomers of C44HH1010..

==

==

Page 21: CH3b Isomers

Draw all of the isomers with the formula C4H9Cl.

Cl

Cl

Cl

Cl

Stereoisomers

Page 22: CH3b Isomers

Draw all of the isomers with the formula C4H9Cl.

ClH HCl

Are these two structures identical?

Page 23: CH3b Isomers

Draw all of the isomers with the formula C4H9Cl.

HCl

A 1:1 mixture of enantiomers is called a racemic mixture.

ClH+ H Cl +

Page 24: CH3b Isomers

HCl

HCl Are these two

structures identical?

mirror

Page 25: CH3b Isomers
Page 26: CH3b Isomers
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Page 30: CH3b Isomers

Isomers ?

C CBr

CH3

Br

H3CC C

CH3

Br

Br

H3Cand

Cis - same side Trans - across

Cis-trans isomers are also called geometric isomers.There must be two different groups on the sp2 carbon.

C CH3C

H H

HNo cis-trans isomers possible


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