organic chemistry Flashcards

1
Q

what is the formula of isobutyl

A

CH3CH(CH3)CH2

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2
Q

what is the formula of sec-butyl

A

CH3CH2CHCH3

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3
Q

what is the formula of tert-butyl

A

CH3CH(CH3)CH3

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4
Q

boiling point increases with

A

more carbons
less branching
polarity
more halides (less F though)
weight

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5
Q

melting point increases with

A

compact molecules (odd #c chains are less compact than even #c)

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6
Q

what is a conformational isomer/conformer

A

different spacial arrangement of atoms as a result of the rotation about a single bond

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7
Q

anti vs gauche bonds

A

anti 180
gauche 60
between adjacent carbons in staggered conformation

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8
Q

what is torsional strain

A

repulsion between aligned electron pairs in eclipsed bonds

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9
Q

what is steric strain/van der waals strain

A

atoms are too close together and destabilizing this compound

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10
Q

what is angle strain and when does it happen

A

happens in cycloalkanes
distortion of bond angles from normal values as a result from a weak bond/poor overlap of orbitals

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11
Q

what are stereoisomers

A

same atom connection but different arrangement in space (cis vs trans)

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12
Q

chiral vs achiral

A

chiral: mirror images but not superimposable
achiral: superimposable mirror images and potentially a line of symmetry

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13
Q

what is an enantiomer

A

chiral stereoisomers

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14
Q

in newman projections where the Y is upside down the left side and right side are dashes or wedges

A

left are wedges and right are dashes

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15
Q

conditions for optical activity

A

substance must be chiral
one enantiomer has to be present more than the other

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16
Q

molecules that rotate in light clockwise vs counterclockwise are called what and have what charge

A

clockwise: dextrorotatory and +
counterclockwise: levorotatory and -
enantiomers rotate opposite directions

17
Q

specific rotation formula

A

[a] = a (observed rotation) / length (dm) x concentration (g/mL)

18
Q

three formulas relating to enantiomeric excess

A

ee = observed specific rotation / a of pure enantiomer
ee % = % major - % minor
100% = % major + % minor

19
Q

what are diastereomers

A

stereoisomers that are not mirror images
one chiral center stays the same
cis and trans are diastereomers

20
Q

what is a meso compound

A

achiral molecule with chiral centers (plane of symmetry)
optically inactive

21
Q

when adding halogens to alkenes what stereoisomers are formed based on cis/trans conformation

A

cis: stereoisomers are (S,S) and (R,R)
trans: stereoisomers are (R,S) and (S,R)

22
Q

what do Sn and E reactions give as products

A

Sn2: single product (inverted con.)
Sn1: single product unless halogen is bonded to chiral center then its enantiomers (R and S)
E2: E and Z isomers unless only one beta carbon has H then only one product (E is m.p.)
E1: E and Z isomers are formed (E is m.p.)

23
Q

what does anticoplanar mean

A

atoms that are 180 degrees apart
adjacent axial atoms are anticoplanar

24
Q

product distribution formula

A

p.d. = (number of Hs)(relative reactivity) / sum of relative amount of all products

25
Q

what factors decrease the predicted stability of a resonance contributor

A

atom with incomplete octet
negative charge on atom that isnt the most EN one
positive charge on EN atom
separated charges

26
Q

what groups donate electrons by resonance

A

NH2 OH OR Cl
more basic substituent

27
Q

what groups withdraw electrons by resonance

A

C=O C(3-)N NO2 SO3H
more acidic substituent

28
Q

huckel’s rule

A

4n + 2 = # of pi electrons

29
Q

criterias for aromaticity

A

cyclic, planar, not sp3 (need p orbital)
odd number of pairs of pi electrons

30
Q

styrene formula

A

benzene-CH=CH2

31
Q

benzyl group formula

A

benzene-CH2

32
Q

what is an incipient carbocation

A

being formed so intermediate with dashed lines