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Organic Chemistry > Exam 2 > Flashcards

Exam 2 Flashcards

(61 cards)

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1
Q

What is a constitutional isomer?

A

different molecule, same molecular formula

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2
Q

What is a conformational isomer?

A

different 3-D shape of the same molecule

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3
Q

What is a staggered conformation?

A

The back atoms are evenly spaced from the front atoms

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4
Q

What is eclipsed conformation?

A

the back atoms are directly behind the front atoms

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5
Q

Is staggered or eclipsed conformation favored and why?

A

stagger… lower energy conformation

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6
Q

What is a dihedral angle?

A

angle in Newman projection between two bonds, one to the front atom and one to the back atom

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7
Q

What is torsional strain?

A

repulsion between bonds when eclipsed

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8
Q

What is steric strain?

A

When non-bonded atoms are too close, causes higher energy (depends on size… amount of strain can vary)

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9
Q

What is gauche?

A

adjacent, large molecules in a staggered conformation

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10
Q

What is anti?

A

large molecules are opposite each other in staggered conformation

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11
Q

What is syn?

A

large groups are eclipsed with each other

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12
Q

Where should the largest groups be in order for the molecule to be in its lowest energy conformation?

A

anti

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13
Q

Where should the largest groups be in order for the molecule to be in its highest energy conformation?

A

syn

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14
Q

Can cyclic molecules rotate bonds?

A

no, they would break

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15
Q

What is angle strain?

A

strain caused by bonds angles being significantly different than what they ideally should be

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16
Q

Which molecule has the butterfly conformation?

A

cyclobutane

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17
Q

Which cyclic molecule has no angle strain?

A

cyclopentane

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18
Q

Which cyclic molecule has the envelop conformation?

A

cyclopentane

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19
Q

What type of strain is present on the envelop conformation?

A

minimal amount of torsional

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20
Q

What is the conformation of cyclohexane?

A

chair conformation

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21
Q

What are the two group types present on a chair conformation?

A

axial and equatorial

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22
Q

What direction does an axial group point?

A

the direction of the bond its coming from

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23
Q

What direction does an equatorial bond point?

A

parallel to the C-C bond in front of or behind it

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24
Q

Why is a boat conformation not as favored as the chair conformation?

A

causes two groups to eclipse so its higher in energy

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25
What does cis mean?
both substituents are on the same side of the plane
26
What does trans mean?
substituents are on opposite sides of the plane
27
What is a stereoisomer?
molecules that have the same molecular formula and atom connectivity but differ in the 3-D arrangement of atoms in space
28
What is a chiral center?
SP3 atom with four DIFFERENT groups attached to it
29
How do you assign priorities to chirality centers?
highest atomic number goes first, make sure number four group is point back
30
Which direction is the R configuration?
clockwise
31
Which direction is the S configuration?
counterclockwise
32
How do you determine the amount of stereoisomers for a molecule with more than one chiral center?
2^n n=chiral centers
33
what is an enantiomer?
Stereoisomers mirror image.. different configuration at all centers
34
What is a diastereomer?
Stereoisomer that is not a mirror image, not all centers change configurations
35
What is a meso compound?
molecules that posses chiral centers but are optically inactive due to plane of symmetry
36
Which way are 'forward' groups' represented on Fischer projections?
to the left
37
Which way are 'backward' groups represented on Fischer projections?
to the right
38
What is a D- designation?
high priority on the right
39
What is a L- designation in a fischer projection?
high priority on the left
40
What is the E- designation?
two top priorities are on opposite sides of double bond
41
What is a Z- designation?
two top priorities are on the same side of the double bond
42
What is true of the physical properties of an R-,R- or S-,S- molecule?
they are all the same except they have opposite sign for rotation of light
43
What is the optical rotation of an chiral molecule?
0
44
What is meant by dextrorotary?
clockwise rotation of light, alpha > 0, + or d
45
What is meant by levorotary?
counterclockwise rotation of light, alpha < 0, - or l
46
What is true of physical properties of diastereomers?
not mirror images so all properties are different
47
What are optical isomers?
stereoisomers that are optically active
48
What is optically active?
rotate plane polarized light
49
What is a terminal functional group?
can only be found at the end of the chain or the outside of a ring
50
What FG is oxo- used for?
aldehyde
51
What is the prefix for nitriles when there is a higher priority group present in the molecule?
cyano-
52
What is the prefix for an aldehyde at the end of a chain?
-oxo
53
What is the prefix for an aldehyde branching off a chain or ring?
formyl-
54
What is the suffix for an acid chlorine?
-oyl chloride
55
What is the suffix for an ester FG in a chain?
-oate
56
What is the suffix for an ester FG branching off a ring?
-carboxylate
57
What is the suffix for NO2?
nitro
58
What is the suffix for OCH3?
methoxy
59
What is the suffix for OCH2CH3?
ethoxy
60
What is the suffix for SCH3?
methylthio
61

Organic Chemistry (4 decks)

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