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My MCAT Cards > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

1
Q

determining R/S

A

lowest in back, determine direction
Fischer – ignore #4, determine direciton, flip to its opposite (R>S, S>R)

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2
Q

polar protic solvent on nucleophiles

A

nucleophiles stronger DOWN periodic table

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3
Q

polar aprotic solvent on nucleophiles

A

nucleophiles stronger UP periodic table

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4
Q

phenols

A

OH groups on aromatic ring
H is very acidic due to resonance stabilization of O-

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5
Q

1° OH –> aldehyde

A

PCC ONLY
rare

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6
Q

1° OH –> COOH

A

most strong OA’s

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7
Q

2° OH –> ketone

A

PCC
or STRONG OA

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8
Q

mesylate/tosylates

A

make OH groups on alcohols better LG’s
protect OH groups because they don’t react

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9
Q

acetal vs hemiacetal

A

hemiacetal = RO-C-OH
acetal = RO-C-OR
make by adding 1 or 2 alcohols (-OR)

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10
Q

stabilization of C-

A

EWG stabilize -
EDG destabilize -
(opposite for C+?)

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11
Q

michael addition

A

form C-C bonds!
1. base deprotonates alpha carbon, enol–enolate ion
2. enolate ion (Nuc) attacks alpha-beta unsaturated C=C bond, bonds NEW C-C

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12
Q

claisen condensation

A

form new C-C bond
occurs between 2 esters or cabonyl-containing compounds
makes a beta-keto ester (ester + another C=O on B-carbon)

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13
Q

more stable conjugate base = stronger acid

A

EWG stabilize conjugate base and increase acidity
EDG destabilize conjugate base and lower acidity

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14
Q

reactivity: carbox acid derivatives

A

anhydrides > esters = carbox acid > amides
all derivatives formed by condensation rxn with COOH and nucleophile

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15
Q

amides

A

nuc. acyl sub with COOH + amine/ammonia
cannot occur with tertiary amines
cyclic amides = lactams

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16
Q

esters

A

nuc. acyl sub with COOH + alcohol (ROH)
esterification produces water (condensation)
fischer esterification (acidic cond.) – carbonyl attacked by alcohol
cyclic esters = lactones
no H-bonding, lower boiling point than alcohols

17
Q

annhydrides

A

2x COOH’s – OH of one attacks C=O of other
cleavage: nuc attacks C=O of one, kicks other COOH off as a LOG

18
Q

induction

A

distribution of charge across SIGMA bonds
polarity

19
Q

conjugation and resonance

A

alternating single and multiple bonds
very stable compounds
stabilize + charge after nucleophilic attack = high reactivity

20
Q

ring strain

A

lactams/lactones can be more reactive when there is ring strain
eg. antibiotics have B-lactams (high reactivity), some bacteria have enzymes that break these rings as a mechanism of resistance!

21
Q

annhydride cleavage

A

nuc attacks one C=O, kicks other COOH off as LG
1. Nuc = NH3 = amide + COOH
2. Nuc = ROH = ester + COOH
3. nuce = H2O = 2x COOH

22
Q

transesterification

A

new alcohol (nuc) attacks C=O of ester + replaces old ROH group in ester

23
Q

AA’s

A

alpha carbon is chiral (except Gly)
ONLY L-isomers EXIST (NH2 on L side in fischer)

24
Q

strecker synthesis of AAs

A
  1. aldehyde > protonate to OH+ > NH3 attacks carbonyl > lose H2O as LG > CN- nuc attacks C=N, bumps up bond to form Nitrile
  2. protonate nitrile > H2O attacks twice (2x OH), carbonyl reforms + kick off NH3 as LG
25
Q

gabriel synthesis of AAs

A

begins with potassium pthalimide & diethyl bromomalonate

26
Q

peaks on IR spectroscopy

A

OH (alcohol) = 3300 broad
OH (carbox acid) = 3000 broad
NH = 3300 SHARP
C=O = 1750 SHARP

27
Q

IR spectroscopy

A
  • measures molecular vibration
  • determines FUNCTIONAL groups
  • look at fingerprint region = 1400-4000 cm-1 (wavenumber = frequency = 1/wavelength)
28
Q

UV-vis spectroscopy

A
  • useful for studying systems with conjugated rings
  • high conjugation = low energy gap = higher wavelength absoption (eg. red)
29
Q

NMR spectroscpy

A
  • measure allignment of nucelar spin with magnetic field
  • determine connectivity
  • spectrum is frequency VS absorption
  • uses “chemical shift” in ppm
30
Q

reading NMR spectroscopy

A
  • hieght of peak proportional to # of H’s
  • each peak group is a UNIQUE H group (different carbons) unless molecule symmetrical
  • splitting: # of peak splits = n + 1 (n = # of other H’s surrounding on adjacent C’s)
  • further LEFT = DESHIELDING by EWG or multiple bonds
  • peak at 0ppm = TMS control (ignore)
  • ORDER (L-R): COOH > aldehyde > aromatic > halide > alkane
31
Q

SN1

A

The reactivity of an SN1 mechanism decreases as 3o > 2o > 1o
If dissociation of LG produces tertiary C+, EDG’s stabilize it more

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