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Organic Chemistry Flashcards

1
Q 
Suffixes for Functional groups
alkane
alkenes
alkynes
alcohols
aldehydes
ketones
carboxylic acids
esters
amides
anhydrides
dicarboxylic acids
A
  • ane= alkane
  • ene
  • yne
  • ol or hydroxy-
  • al or oxo-
  • one or oxo-
  • oic acid
  • oate or alkoxycarbonyl-, lactone if cyclic
  • amide or carbomoyl-, amido- or lactam if cyclic
  • anhydride
  • dioic acid
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2
Q

Order of lowest to highest priority

A 
alkane
alkenes
alkynes
alcohols
ketones
aldehydes
amides
esters
anhydrides
carboxylic acids
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3
Q

Fischer diagram rules

A

into plane/dashes= vertical lines
out of plane/wedges= horizontal lines

switching one pair/rotate 90= invert stereochem
switching two pairs/rotate 180= retains stereochem

lowest priority group should be vertical. If not:
-swap one pair, find R/S and take opp
OR
-find R/S normally and take opp

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4
Q

Factors that affect nucleophillicity

A

Increase:

  • negative charged
  • low electronegativity
  • low sterics

protic solvent= weak base is better nuc (I>Br?Cl>F)
aprotic solvent= strong base better nuc (F->Cl>Br>I)

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5
Q

Sn1 vs Sn2

A

Sn1- two steps, formation of carbocation is RDS, next attack of nuc. More hindered electrophile better. Racemic usually formed. Rate dependant only on elec.

Sn2- concerted, rate dependant on both nuc and elec., less hindered electrophile better, inversion of stereochem

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6
Q

oxidation reactions and common reagants

A

feature increase in number of bonds to oxygen

PCC, CrO3/pyridine, H2CrO4, KMnO4, O3, mCBPA,

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7
Q

reduction reactions and common reagants

A

feature increase in number of bonds to H

LiAlH4, NaBH4

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8
Q

Properties of Alcohols and Phenols

A

alcohols= hydrogen bonding= high MP/BP

weakly acidic but phenols more acidic due to resonance stabilization of CB

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9
Q

Oxidation of Alcohol rxns

A

PCC
Primary to aldehydes
secondary to ketones-

Na2Cr2O7 + K2Cr2O7 and Jones Oxidation (CrO3+ H2SO4+ acetone)
primary to carboxylic acids
secondary to ketones

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10
Q

Mesylates and tosylates

A

make alcohols better LV
protect alcohol from reaction- especially oxidization

ROH+ MsCl/TsCl= ROMs or ROTs and when nuc attacks= R-nuc +MsOH

look up strructure of mesylate/tosylate

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11
Q

Acetal/ketal formation + purpose

A

HO-R_OH (diol) + aldehyde/ketone= acetal/ketal

protection from LiALH4!!!!!
deprotection with acid

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12
Q

Quinone, hydroxyquinone, ubiquinone

PLEASE REMEMBER STRUCTURES! ADD TO ANKI OR SOMETHING

A

Oxidized phenol= quinone (double bond O vs OH)— vitamins K1 and K2
hydroxyquinone= quinone with additional hydroxyl groups on ring
ubiquinone= coenzyme Q- electron carrier on Complex 1,2,3, lipid soluble so e- carrier in bilayer

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13
Q

Ketone, Aldehyde- properties/reactivity compared to eachother

A

aldehyde more reactive to nucs (less steric)
good electrophiles
high BP (dipole) but no H-bonding so less than ROH
alpha H= acidic— ketones have less acidic since donating alkyl groups destabalize carbanion

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14
Q

From aldehydes and ketones,

how are acetals, hemiacetals, and geminal diols formed

how are imines, enamines, and cyanohydrins formed

A

nucleophillic substitution

hemiacetal- ROH attack (nuc sub)

acetal- OH protonated, water lost, and then ROH attack again (ike Sn1)

geminal diol= water attack, O- pulls H from water

cyanohydrin= OH and CN present on molecule following nuc substitution

imines=NH3, NH2OH, H2N_NH2 react via nuc sub under acidic conditions. OH protonated, water lost and double bond with N formed

enamine= double bond between Cs instead of CN. tautomerization of imine (not thermo favored)

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15
Q

Oxidation of aldehydes

A

Go to carboxylic acids

KMnO4, CrO3, Ag2O H2O2

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16
Q

Reduction of ketones/aldehydes

A

LiAlH4 or NaBH4– go to respective alcohol

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17
Q

Keto vs Enol and enolate formation

A 
keto= more favored/common
enol= CC double bond. tautomerization. Racemization if chiral carbon 
enonate= nuc= formed by deprotonation of alpha C by strong base= LDA, OH, KH

alpha C in between two carbonyls= highly acidic

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18
Q

Michael rxn

A

review!!!!!! alpha-beta unsaturated carbonyl attacked y enolate

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19
Q

Kinetic vs thermo enolates

A

thermodynamic= enolate formed on more substituted alpha carbon.
high temps, slow reversible rxns, weak small bases

kinetic= enolate formed on less substituted alpha c (less steric- good intermediate)
low temps, fast irreversible rxns, strong sterically hindered base

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20
Q

Aldol condensation

A

Aldol formation.
enolate formed by deprotonation. Enolate acts as nuc and attacks carbonyl (nuc addition)

strong base, high temps= dehydration
alpha H removed and double bond formed with C that was an electrophile during nuc sub, kicking off the OH

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21
Q

retro aldol condensation

A

split alphabeta unsaturated carbonyl into two carbonyls

base added, heat applied

22
Q

properties of carboxylic acids

A

H-bonding (both O)— higher BP than ROH

acidity of hydroxyl OH
e-withdawing groups like NO2 increase acidicty, aklkyl groups decease, electron donating like NH2 and OCH3- decrease

dicarboxylic acids
first H- more acidic
second H- less acidic (repulsion of -)

alpha H in beta dicarboxylic acids are less acidic than hydroxyl H

23
Q

synthesis of carboxylic acids

A

oxidation of primary alcohols and aldehydes

KMnO4, CrO3, NaCr2O7

24
Q

Nuc acyl substitution to form amides,esters, anhydrides

A

RCOOH+ RNH2 (NH3, primary, secondary amines)—– amide

RCOOH + ROH (primary)- ester
protonate double bond O to make more electrophillic (acidic conditions)- Fischer esterification
look up mech.
anhydride+ alcohol= ester
triacylgyclerols= esters of fatty acids and glycerol

RCOOH + RCOOH- anhydride

25
Reduction of carboxylic acids
only by LiAlH4 to alcohol , not NaBH4 nuc acyl sub with addition of H- to form aldehyde. Then nuc addition of H-
26
Saponification
long chain carboxylic acid (fatty acid) + NaOH/KOH= polar head, nonpolar tail. micelles
27
B keto acid decarboxylation
intramolecular rxn - sponatenous under heat enol formation, keto tuatomeriztion CO2 release please!!!!!! image
28
rank reactivity (electrophillicity) of carboxylic acid derivatives for nucleophillic acyl substitution
acid chloride > anhydride> esters> amides
29
Anhydride cleavage
nuc acyl substitution anhydryide + amine= carboxylic acid + amide anhydride + alcohol= carboxylic acid+ ester anhydride + water= two carboxylic acids
30
transesterification
ester + alcohol- replace OR group in ester
31
amide hydrolysis
need strong acid or base--- get carboxylic acid + amine acidic conditions - protonate carbonyl O, nuc acyl sub, nuc=water basic conditions= nuc=OH-
32
IR wavenumber
1/wavelength
33
Which stretches do not show up on IR spectra?
Symmetric stretches do not show up in IR spectra- no net change in dipole moment O2, Br2- silent
34
IR spectras to know for MCAT OH NH C double bond O C triple bond O or N alkane alkene alkynes
OH- broad peak around 3300 and around 3000 for carboxylic acids NH- sharp peak 3300 C=O - 1700-1750 1900-2200 2800-3000 3000-3150 3300
35
UV spectroscopy - which compounds is it useful for studying. How are HOMO and LUMO related
most useful for studying compounds with double bonds or with lone pairs (pi or nonbonding electrons and conjugated systems) smaller the difference between HOMO and LUMO, longer the wavelengths that can be absorbed by the molecule
36
NMR spectroscopy deshielding and what makes proton deshielded chemical shifts to know
Deshielded- higher chemical shift- occurs when protons electron density being pulled away (e-withdrawing groups) e- donating groups= shielding= lower chemical shift remember splitting ``` chemical shifts to know- alkyl (0-3) alkynes (2-3) alkene( 4.6-6) aromatics (6-8.5) aldehydes (9-10) carboxylic acids (10.5-12) ```
37
Extraction
like dissolves in like. used to get product and separate out impurites (wash). aqueous and organic layer- density determines order on top to bottom add water and shake and extract etc. multiple times= better yield. Use rotovap to remove solvent if acid product: - add base= acid extracted into aqueous phase. - anion goes in aqueous phase
38
When to use gravity vs vacumn filtration
gravity= product is in filtrate (liquid) | vacuum- product is the solid
39
recrystallization
solvent chosen- product only soluble at high temps so desired product recrystallizes upon cooling, exlcuding impurities
40
distillate
liquid with lower BP evaporates and condenses and collects- called distillate
41
simple vs fractional vs vacuum distillation
vacuum- high BP liquid distillation fractional- too similar BPs
42
TLC/Paper Chromatography
TLC- use silica gel Paper- use cellulose after spotting and set up in beaker, eluent climbs the plate (capillary action) polar and hydrophilic stationary phase mobile phase is weak polarity polar samples stick to the plate- move up less (low rf) nonpolar samples move further up plate (high rf)
43
Reverse phase chromatography
stationary phase nonpolar polar move up plate quickly (high rf) nonpolar sample stick and move up less (low rf)
44
Column chromatography Ion exchange size- exclusion affinity
Used to separate compounds- including macromolecules Stationary phase= column with silica or alumina beads-adsorbent Mobile phase= nonpolar solvent- travels through column down by gravity Ion-exchange chromatography= beads coated with charges substances to bind compounds with opp charges. (DNA ex) Size exclusion chromatography=beads have small pores to trap small compounds and allow larger compounds to pass through fast Affinity chromatography=beads coated with receptor or antibody to compound to have high affinity for it
45
Gas chromatography
separates vaporizable compounds according to how well they adhere to absorbent in column stationary phase= coil of metal/polymer mobile phase= nonreactive gas can be combined with mass spectrometry= determines molecular weight
46
High performance liquid chromatography (HPLC)
computer mediated solvent and temperature gradients used used is small sample size or forces like capillary action will effect results
47
Synthesis of AA- Strecker Synthesis
1. start with aldehyde (protonated). R group is r of AA., NH4Cl, KCN. Ammonia attacks, form imine (keep this amine) CN attack, form nitrile (eventually kicked off) Molecule formed is aminonitrile 2. Nitrile protonated. Water attacks, forming imine with hydroxyl. Water attacks again. Form carbonyl again, deprotnonate, and lose NH3. Amino acid formed. L and D amino acids generated.
48
Gabriel Synthesis
malonic ester synthesis potassium phthalimide (acidic, nucleophillic anion) attacks diethyl bromomalonate (Br is LV) base deprotonates, leaving compound to act as nuc and attack R-Br, attaching R group. molecule hydrolyzed with strong base and heat- separaton. U need pics. dicarboxylic acid with R group and amine group formed. Then dexocarboxylated via acid + heat. Formation of amino acid L and D AA generated
49
Inorganic phosphate
H2PO4-2 and HPO4-2 = Pi inorganic phosphates
50
Pyrophosphate
PPi (p2O7-4) released when phosphdiester bonds formed. Later hydrolyzed to two inorganic phosphate (Pi)
51
Reason why phosphate bonds high energy
adjacent negative charges, resonance stabilization of phosphates
52
Phosphoric acid
3 hydrogens. Acts as buffer over large range of pH values since varying pKas

MCAT (5 decks)

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