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MCAT > OChem > Flashcards

OChem Flashcards

1
Q

what bond is shorter, double or single?

A

double

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2
Q

what geometry is this?

A

bent

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3
Q

what geometry is this?

A

trigonal planar

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4
Q

what is the range of charges for oxidation state?

A
  • 4 to +7
  • treat bonds as if they are ionic bonds where most electronegative atom will get transferred the electrons
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5
Q

how do you calculate bond order?

A

number of bonds/number of attached atoms

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6
Q

how do you calculate fractional charge?

A

total charge of attached atoms/number of atoms

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7
Q

honc equation?

A

(# of bonds) - (honc #) = formal charge

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8
Q

what is this structure?

A

isopropyl

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9
Q

what is this structure?

A

sec-butyl

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10
Q

what is this structure?

A

tert-butyl

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11
Q

what is this structure?

A

iso-butyl

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12
Q

CH3COOH

A

acetylaldehyde

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13
Q

what is this structure?

A

propanone (acetone!!)

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14
Q

what is this structure?

A

acetic acid

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15
Q

what is this structure?

A

formic acid

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16
Q

what is this structure?

A

benzoic acid

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17
Q

what is this structure?

A

salicylic acid

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18
Q

what is the suffix for aldehyde?

A

-anal

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19
Q

what is the suffix for ketones?

A
  • anone
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20
Q

what is the suffix for carboxylic acid

A
  • anoic acid
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21
Q

what is the suffix for esters

A
  • anoate
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22
Q

what is this structure?

A

methyl acetate

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23
Q

EZ system

  • when the two higher priority groups on the same side of the double bond, what is it?
A

Z (ze zame zide)

E - when the highest priority groups are on opposite sides of the double bond

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24
Q

nomenclature of benzene derivatives:

ortho -

A

(1,2) - beside eachother on benzene ring

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25
Q

nomenclature of benzene derivatives:

meta

A

(1,3) - separated by 1 carbon on benzene ring

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26
Q

nomenclature of benzene derivatives:

para

A

(1,4) - across from eachother on benzene ring

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27
Q

what is phenol

A

a benzene with a hydroxyl group

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28
Q

what is benzoic acid

A

benzene with carboxylic acid attached

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29
Q

what is benzaldehyde

A

benzene with aldehyde attached

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30
Q

what is toluene

A

benzene with methyl group attached

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31
Q

what is aniline

A

benzene group with NH attached

32
Q

what is the order of stability of the conformations of butane? (eclipse, anti… etc.)

A

anti (methyl groups are 180 degrees apart)

guache (where there is some steric hinderance of methyl groups)

eclipse (where methyl groups are not directly eclipsed ontop of each other)

eclipse (where the two methyl groups are directly eclipsed on each other)

33
Q
A
34
Q

do enantiomers share the same physical and chemical properities?

A

they share the same physical properites - except the rotate around polarized light in opposite directions

  • they share the same chemical properties unless when reacting with another chiral reagent
35
Q

do diastereoisomers have the same physical/chemical properties?

A

share similar chemical properties but vary in their physical properties

36
Q

what are meso compounds or meso isomers?

A

A meso compound or meso isomer is a non-optically active member of a set of stereoisomers, at least two of which are optically active. This means that despite containing two or more stereogenic centers, the molecule is not chiral. A meso compound is “superposable” on its mirror image

37
Q

how are conformational isomers produced?

A

rotation around a single bond

38
Q

when are two isomers resolvable?

when are isomers interconvertible?

A
  • when there is no small energy barrier separating the two
  • when there is a small energy barrier separating the two (such as the conformational isomers of butane)
39
Q

what is chromatography in association with a chiral stationary phase used to separate?

A

enantiomers

  • one enantiomer will move up the plate slower than the other
40
Q

What are the two rules of thumb when dealing with Fischer projections of carbohydrates?

when the hydroxyl group is on the right, what configuration?

left?

A

when the hydroxyl group is on the right, the configuration is R, and when it is on the left, the configuration is S.

41
Q

what is the equation for specific rotation of enantiomers?

A

= a(observed)/cxL

c= concentration

l = length of tube in dm

42
Q

what is a single bond, double bond, and triple bond? (σ and pi)

A

single - sigma

double - sigma and pi

triple - sigma and two pi

43
Q

what is a coordinate covalent bond?

A

when the two electrons that form the covalent bond come from the same atom (the lewis base - electron donor)

44
Q

smaller the pKa, _____ the acid

A

stronger (-2 and below is considered strong acid, -2 to 20 considered to be a weak organic acid)

45
Q

what are some functional groups that act as bases? acids?

A

bases - amines, amides

acids - aldehydes, carboxylic acid, carboxylic derivatives, ketones, alcohols

46
Q

nucleophiles - dependent on 4 things. does nucleophilicity increase or decrease with each?

charge

electronegativity

steric hinderance

solvent (protic vs aprotic polar)

A

more negative charge, higher nucleophilicity

more electronegative, less nucleophilic

more steric hinderance, less nucleophilic

protic solvents increases nucleophilicity DOWN periodic table (I > Br > Cl > F)

aprotic solvents decrease nucleophilicty UP periodic table (F > Cl > Br > I)

47
Q

heterolytic reactions

A

opposite of coordinate covalent bonds

  • electron pair is given to one of the two products
48
Q

in a nucleophilic substitution reaction (SN1), what is the rate limiting step?

A

formation of the carbocation, meaning that only the concentration of the substrate determines rate of reaction (not the nucleophile)

rate = k[R-L], where R-L is an alkyl with a leaving group

49
Q

why do SN1 reactions usually end with a racemic mixture?

A

because of the carbocation intermediate, where the nucleophil can come in at different sides, creating new steriochemistry

50
Q

what is a concerted reaction?

A

SN2 - bimolecular nucleophilic substitution reaction

  • rate limiting step involves two molecules
51
Q

which reaction is preferred for a sterically hindered carbon? which is preferred for a not sterically hindered carbon? why?

A

sterically hindered - SN1, because the more substituted the carbon is, the more stable the carbocation intermediate is

not - SN2, because it is a front back reaction, where the nucleophile attacks while the leaving group leaves –> more room for attack means better reaction

52
Q

oxidation vs reduction?

A

oxidation is increasing the oxidation state of an atom, for example with carbon, you are bonding it to an atom that is more electronegative (usually O, N, F), you are losing electrons

  • usually increasing amount of bonds to oxygen

reduction is usually bonding the carbon to a lower electronegative atom such as hydrogen, gain electron

53
Q

common reducing agent? common oxidizing agent?

A

reducing - LiAlH4 (containing H-)

metals bonded to hydrides

oxidizing - KMnO4, CrO3 (containing O)

metals bonded to oxygens

54
Q

if a molecule like ethanol is in the presence of an STRONG oxidizing agent, what will happen?

A

will oxidize to carboxylic acid !! will only oxidize to aldehyde if oxidizing agent is in presence of PCC or is a weak oxidizing agent (which will stop the rxn at aldehyde from primary alcohol)

55
Q

is pyridinium chlorochromate a strong or weak oxidizing agent?

is dichromate a strong or weak oxidizing agent?

A

pyridinium is weak

dichromate is strong

56
Q

what property must the solvent have in nucleophilic/electrophilic rxns?

A

polar!! like dissolves like!!

  • protic or aprotic
57
Q

if two substituents on a benzene ring are 1 carbon apart, what letter is it?

2?

across from eachother?

A

1 - o

2 - m

across - p

58
Q

what determines the boiling point of alcohols?

A

the intermolecular H bonding - the more hydroxy groups, the higher the boiling point!

59
Q

acidity of alcohols: put in order of most acidic to least

phenol, i-PrOH, CH3OH

A

phenol

CH3OH

i-PrOH

60
Q

will substituents that are electron withdrawing decrease or increase acidity of alcohols?

electron donating?

examples of each

A

withdrawing - resonance structures, like aromatic structures: will increase acidity

donating (alkyl groups)- will decrease acidity

61
Q

what are mesyaltes and tosylates functions?

difference between mesylate and tosylate?

A

hydroxyl groups are protonated into these to be better leaving groups. also used as protection for alcohols you dont want to react

mesylates- SO3CH4

tosylate - SO3C6H4CH3

62
Q

quinones:

how are they produced?

electrophilic or nucleophilic?

A

reacting phenols with oxidizing agents

electrophilic because of electron withdrawing groups in the resonance structures of the carbonyl groups

63
Q

what is ubiquinone?

A

coenzyme Q

64
Q

what does jones oxidation reactions require besides oxidizing agent and solvent?

A

dilute sulfuric acid

65
Q

acetals and hemiacetal rxns with ketones/aldehydes:

1 equivalent of alcohol will produce what?

2 equivalents of alcohol?

A

hemiacetal/hemiketal

acetal/ketal AND WATER!!!

  • can be reversed in aqueous solution
66
Q

what is a cyanohydrin?

A
  • HCN + aldehyde or ketones
  • rxns with aldehydes and ketones will form cyanohydrins once oxygen is reprotonated
67
Q

what kind of rxn is nitrogen/nitrogen-containing derivatives reacting with aldehydes and ketones?

A

since a small molecule is lost, it is called a condensation rxn

  • as well as a nucleophilic substitution rxn
68
Q

to form a geminal diol, what could you add to attack the carbonyl carbon?

A

water

69
Q

the electron withdrawing oxygen ________ carbanion (negatively charged carbon)

alkyl groups tend to _______ organic anions

(stabilize or destabilize)

A

the electron withdrawing oxygen therefore helps stabilize carbanion (negatively charged carbon)

alkyl groups tend to destabilize organic anions

70
Q

electron-withdrawing (or resonance) – like aromatic structures, it will _______ acidity

A

increase!!!!!

71
Q

how are enols formed?

A

Enols – formed using a strong base on ketones/aldehydes (OH-, LDA, KH)

72
Q

Michael addition? a carbanion attacks an __________ compound

A

Michael addition – a carbanion attacks an a,B-unsaturated carbonyl compound – a molecule with a multiple bond between the a and B carbons next to a carbonyl

73
Q

during formation of enolates from differently substituated ketone a-carbons, there are two different enolates that can form; thermodynamic and kinetic

under what conditions (temperature, reversible/irreversible/strength of base used, rate of rxn) are kinetic enolates formed and what conditions are thermodynamic enolates formed?

where is the double bond formed in kinetic enolates vs thermodynamic?

A

kinetic enolates – formed in rapid, irreversible, high temperature and strong base reactions

  • double bond will form between the carbonyl and a-carbon that is least substituted

thermodynamic enolates – formed in slow, reversible, low temperature, weak base reactions

  • double bond will form between the carbonyl and a-carbon that is more substituted
74
Q

aldol condensation - what are the reactants and what is the product?

aldol ?

retro-aldol reaction - what are the optimal conditions and what happens in this reaction?

A

aldol condensation – nucleophilic addition to a carbonyl except the ketone/aldehyde acts as the electrophile and the enol tautomer acts as the nucleophile to form a carbon-carbon bond to form aldol

  • after aldol is formed, a dehydration reaction occurs which results in an a,B-unsaturated carbonyl

aldol -contains both alcohol and aldehyde functional group

retro-aldol reaction – base is added and heat is applied

  • results in the breakage of the a, B-carbon bond
75
Q
A

MCAT (6 decks)

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