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Organic Chemisty > Chapter 2 - Isomers > Flashcards

Chapter 2 - Isomers Flashcards

1
Q

Structural (constitutional isomer )

A

Molecular formula and molecular weights are all the same

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2
Q

Physical properties

A

Processes that don’t change the composition of matter

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3
Q

Examples of physical properties

A 
Melting point
Boiling point 
Solubility 
Odor 
Colour 
Density
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4
Q

Chemical properties

A

Change the composition of matter by reacting with other molecules
Functional groups of molecule *

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5
Q

Acetone structure

A

CH3-C(O)-CH3

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6
Q

Stereoisomers

A

Share same atomic connectivity

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7
Q

Conformational isomers

A

Rotate around a single bond

- same molecule but are in a different point of rotation

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8
Q

Configurational isomer

A

Only interconverted by breaking a bond

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9
Q

Newman projection

A

Visualized along a line extending through carbon carbon axis

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10
Q

Staggered ( anti ) conformation

A

When two largest groups are 180 degrees apart

Most stable conformation

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11
Q

Staggered (gauche) conformation

A

Two largest groups are 60 degrees apart

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12
Q

Staggered ( eclipsed ) conformation

A

The two largest groups are 120 degrees apart

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13
Q

Totally eclipsed

A

Highest energy state

When the two largest groups are semiplanar

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14
Q

What are three types of ring strain ?

A

Angle strain
Torsional strain
Nonbonded strain

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15
Q

Angle strain

A

Bonded angles deviate from their ideal values by being stretched or compressed

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16
Q

Torsional strain

A

When cyclic molecules assume eclipsed or gauche interactions

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17
Q

Nonbonded strain ( van der waals repulsion )

A

Nonadjacent carbons compete for the same space

18
Q

Axial

A

Hydrogen atoms that stick up or down

19
Q

Equatorial

A

Hydrogens that stick out

20
Q

Chair flip

A

All axial become equatorial and vice versa

21
Q

What conformation do bulkier groups favour ?

A

Equatorial

22
Q

What happens in rings with more than one substituent ? Which conformation is favoured ?

A

The preferred chair position is the one in which the larger group is in the equatorial position

23
Q

Cis

A

If both groups are located on the same side of the ring

24
Q

Trans

A

If both groups are located on the opposite side of the ring

25
Q

Chiral

A

Mirror image that can not be super imposed

26
Q

Chiral center

A

Carbon is bonded to 4 different substituents

27
Q

Enantiomer

A

Nonsuper imposable mirror image

Nearly identical physical and chemical properties except optically activity and reactions in chiral environment

28
Q

Diastereomers

A

Chiral and have the same connectivity
Not mirror images
Each have different chemical properties but may behave similarly due to the same functional group
Also rotate plane polarized light which is not equal in magnitude to mirror image
Differs by at least one but not all chiral carbons

29
Q

Optically active

A

Rotation of the plane polarized light by a chiral molecule

Light is rotated in the same magnitude but opposite direction of the mirror image

30
Q

Dextrorotatory (d-) +

A

Polarizes light to the right out clockwise

31
Q

Levorotatory (l) -

A

Compound that rotates light counterclockwise or to the left

32
Q

What does the amount of rotation of the plane polarized light depend on ?

A

Concentration of optically active compound

Length of tube

33
Q

Specific rotation equation

A

[alpha]=alpha obs/ c x l

[alpha]-specific rotation in degrees
Alpha obs- observed rotation in degrees
C - concentration in g/mol
L - path length in dm

34
Q

Racemic mixture

A

Equal concentrations of (+) and (-) are present so the rotations cancel out and no optical activity is observed

35
Q

Geometric isomer

A

Substituents differ in their position around and immovable bond

36
Q

What is the criteria for a compound to be optically active ? What is a mess compound ?

A
  1. Chiral center
  2. No internal plane of symmetry

Meso compound - chiral carbon + plain of symmetry

37
Q

Relative configuration

A

Spatial arrangement of chiral molecules with respect to other molecules

38
Q

Absolute configuration

A

Spatial configuration of chiral molecules independent of other molecules

39
Q

Z forms

A

Two highest priority group on double bond are on the same side

40
Q

E forms

A

Two highest priority groups on double bond are on opposite sides

41
Q

What compounds require the use of E and Z forms ?

A

Polysubstituted double bonds

Organic Chemisty (4 decks)

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