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MCAT > Isomers > Flashcards

Isomers Flashcards

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MCAT flashcards
1
Q

What is a constitutional isomer?

A

Structural isomer

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2
Q

Structural isomer

A

Same chemical formula and different connectivity

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3
Q

Physical property

A

Characteristics that do not change the composition of a molecule

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4
Q

Chemical Property

A

Related to the reactivity of the molecule which results from changes in the chemical composition

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5
Q

What usually dictates chemical properties?

A

Functional groups

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6
Q

What are the two types of stereoisomers?

A

Conformational and Configurational

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7
Q

Stereoisomers

A

Same formula and connectivity, different spatial arrangement of atoms

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8
Q

Conformational isomers

A

Differ in rotation around single bonds

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9
Q

How are configurational isomers interconverted?

A

Interconverted by breaking bonds

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10
Q

How do you separate a racemic mixture?

A

Add only one enantiomer of another compound to create two diasteromers (++ and +-) or (– and +-)

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11
Q

Most energetically favorable conformational isomer

A

Anti

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12
Q

Least energetically favorable conformational isomer

A

Totally eclipsed

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13
Q

Two types of staggered conformations

A

Anti and Gauche

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14
Q

Axial position

A

Perpendicular to plane of ring

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15
Q

Equatorial position

A

Parallel to plane of ring

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16
Q

What position to bulky groups take in cyclic conformations?

A

Equatorial

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17
Q

What are the two types of configurational isomers?

A

Enantiomers and Diastereomers

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18
Q

Enantiomers

A

Nonsuperimposable mirror images

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19
Q

Nonsuperimposable mirror images

A

Enantiomers

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20
Q

Are diastereomers mirror images?

A

No

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21
Q

Chiral

A

Mirror image cannot be superimposed on original object

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22
Q

Optical activity

A

Rotation of plane-polarized light by a chiral molecule

23
Q

Molecule that rotates light clockwise

A

Dextrorotatory

24
Q

Dextrorotatory designation

A

d- or +

25
Q

d- designation

A

Rotates light clockwise

26
Q

+ designation

A

Rotates light clockwise

27
Q

Molecule that rotates light counter clockwise

A

Levorotatory

28
Q

Levorotatory designation

A

l- or -

29
Q

l- designation

A

rotates light counterclockwise

30
Q
  • designation
A

rotates light counterclockwise

31
Q

Racemic mixture

A

Equal + and -

No optical activity

32
Q

Does a racemic mixture have optical activity

A

No

33
Q

Calculation of specific rotation

A

Specific rotation = observed rotation/(concentration times length of tube)

34
Q

Most stable cyclohexane configuration

A

Chair

35
Q

Diastereomers

A

Contain two or more chiral centers and differ at some but not all of these centers

36
Q

How many stereoisomers does a compound with n chiral centers have?

A

2^n

37
Q

What are geometric isomers?

A

Cis/trans isomers

38
Q

Meso compound

A

Has multiple chiral centers but also contains a plane of symmetry and does not rotate light

39
Q

Is a meso compound optically active?

A

No

40
Q

Relative conformation

A

Configuration in relation to another chiral molecule

41
Q

Absolute conformation

A

Exact spatial arrangement of atoms/groups

42
Q

Z conformation

A

Two highest priority groups around a double bond are on the same side of the bond

43
Q

E conformation

A

Two highest priority groups around a double bond are on opposite sides of the bond

44
Q

Which direction do wedge bonds project?

A

Out of the plane of the page

45
Q

Which direction do dashed bonds project?

A

Into the plane of the page

46
Q

In a fischer projection which direction do vertical lines project?

A

Into the plane of the page

47
Q

In a fischer projection which direction do horizontal lines project?

A

Out of the plane of the page

48
Q

R conformation

A

Clockwise 1-3 around a chiral center

49
Q

S conformation

A

Counterclockwise 1-3 around a chiral center

50
Q

When you skip #4 to assign R/S, will the designation be the same or opposite?

A

Opposite

51
Q

When you make 1 switch to assign R/S, will the designation be the same or opposite?

A

Opposite

52
Q

When you move #4 to the back, how do you further manipulate the Fischer projection and will the designation be the same or opposite?

A

Switch the other two groups and then it will be the same

53
Q

What are the length units in calculation of specific rotation?

A

decimeters (10dm in 1m)

54
Q

What is the concentration unit in calculation of specific rotation?

A

g/mL

MCAT (31 decks)

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