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MCAT chem > functional groups and reacitons > Flashcards

functional groups and reacitons Flashcards

1
Q

hydrocarbon properties

A

low boiling point compared to other functional groups
only intermoleculare force is londen dispersion

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2
Q

do highly branched alkanes have higher or lower boiling points

A

lower because stacking is less efficient

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3
Q

alkyl halides

A

C-X where c is carbon chain and X is a halogen

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4
Q

alkyl halide formation reaction

A
  1. hydrohalogenation
  2. substitution rxn with OH-x
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5
Q

are halogens a good leaving group

A

yes, which makes alkyl haides good reactive subjects for substitution and elimiation

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6
Q

good leaving groups

A

weak bases that want to accept electrons, do not want to share e-
- conjugate base of a strong acid

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7
Q

good nulceophiles

A

want to donate electrons
have increased negative charge
increased bacisty from right to left

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8
Q

hydrogenation

A

reduction of alkenes to alkanes with h2 and a calayst

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9
Q

phenols

A

aromatic ring with an alcohol group attatched

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10
Q

ortho

A

position of substituents on aromatic ring where the are adjacent

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11
Q

para

A

position of substituents on aromatic ring where they are on opposite sides

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12
Q

meta

A

position of substituents on aromatic ring seperated by a carbon

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13
Q

what effect does adding an OH group to a benzene ring have on the boiling point

A

rasises it because of h bonding

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14
Q

pKa of OH

A

weakly acidic with pKa of 15
- less acidic than phenols beacuse resonance

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15
Q

phenol pKa

A

10
- acidity can be increased by EWG
- acidicty decreased by EDG

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16
Q

pcc

A

weak oxidizing agent
primary or secondary oh into a carbonyl

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17
Q

NaCr2O7

A

strong oxidizaing agent
covert primary oh into COOH
convert secondary OH into ketone

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18
Q

K2Cr2O7

A

strong oxidizaing agent
covert primary oh into COOH
convert secondary OH into ketone

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19
Q

CrO3

A

strong oxidizaing agent
covert primary oh into COOH
convert secondary OH into ketone

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20
Q

ubiquinone Q

A

cownzyme Q, electron acceptor between c 1,2,3,

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21
Q

silyl esters

A

Si-O bond forms with OH group to protect it from reagent and is removed by fl-

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22
Q

mesylates

A

react OH with methyl sulfonyl chloride to protect oh group

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23
Q

tosylates

A

react oh with tosyl suflonyl chloride to protect oh group

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24
Q

how to protect carbonyls during reactions

A

form acetals with an equivalent diol which is then removed under acidic conidtion

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25
Q

LiALH4

A

strong reducing agent: reduces both COOH and carbonyls to alcohols

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26
Q

hemiacetals

A

intermediate in the formation of acetals where there is one OH group in replacement of one to the OR groups

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27
Q

aceteal

A

an aldehyde has 2 OR groups

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28
Q

what structure is responsible for acetals and hemiaceltas

A

aldehydes

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29
Q

what structure is assoicated with ketals and hemiketals

A

ketones

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30
Q

hemiketal

A

one of the 2 OR group s of. a ketal is replaced with OH

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31
Q

ketal

A

ketone is replaced by R1, R2, OR1, OR2

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32
Q

aldehyde

A

terminal carbonyl group

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33
Q

ketone

A

carbonyl is within the molecule

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34
Q

boiling points of aldehydes, COOH, and OH in order from lowest to highest

A

C=O<OH< COOH

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35
Q

intermolecular interactions that aldehydes have which alkanes do not

A

dipole dipole

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36
Q

which has a higher melting point? OH or aldehyde

A

OH because of hydrogen bonding

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37
Q

alpha hydrogen

A

the hydrogen adjacent to the carbonyl carbon
- important for ketone and aldehyd ereactions because of resonance stability

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38
Q

pka of aldehyde/ ketone

A

17-19

39
Q

which is more acidic? aldehydes or ketones

A

aldehydes are slightly more acidic than ketones

40
Q

do aldehydes and ketones act as nulceophiles or electrophiles

A

both

41
Q

which part of aldehyde can act as an electrophile

A

the carbonyl carbon has a partial positive

42
Q

which part of the aldehyde can act as a nucleophile

A

the carbanion with negative charge

43
Q

which of the two are more reactive and why between aldehydes adn ketones

A

aldehydes because less steric hinderance

44
Q

what happens when an aldehyde is reacted with PCC

A

nothing , weak oxidizing agent

45
Q

strong oxiidizing agents

A

Na2CO2O7, K2Cr2O7, CrO3, KmNO4, Ag2O, H2O2

46
Q

can a ketone be oxidized by a strong oxidizing agent?

A

no

47
Q

NaBH4

A

weak reducing agent

48
Q

reaction with water and aldehyde

A

nucleophile: water
electrophile: carbonyl carbon
product: geminal diol on carbonyl –> hydration

49
Q

reaction with alchol and aldehyde

A

nucleophile: R-OH
electrophile: carbonyl carbon
product: hemiacetal (would be hemiketal in ketone)

50
Q

reation with hydride (NaBH4 or LiAlH4) and aldehyde

A

aldehyde is reduced to a primary alochol

51
Q

reaction with amide and aldehyde

A

amide is nucleophile
attacks carbonyl carbon and produces imine –> enamine

52
Q

keto form

A

c=o

53
Q

enol form

A

c=c with oh instead of o

54
Q

kinetically favored enolate

A

formed more quickly and less stable
- db tends to invovle less substituted carbon because of less hinderance
- low temp

55
Q

thermodynamic enolate

A

db forms between carbonyl carbon and more substituted carbon , slower and more stable

56
Q

aldol condensation

A

aldehydes and ketones can react with eacother
- nucleophilic enolate and electrophilic carbocation
- molecules join and produce an aldol (aldehyde/ketone + alcohol).

57
Q

aldol elimination

A

when the aldol OH is removed via elimination to produce double bond

58
Q

retroaldol reaction

A

aldol can be reversed back into aldehyde and ketone at high temperatures

59
Q

carboxylic acid derivatives

A

COOH where OH is replaced by something else
- amides, esters, anhydrides

60
Q

physical properties of carboxylic acids are determined by what

A

ability to hydrogen bond
-IMF stronger than alcohols

61
Q

pKa of COOH

A

4

62
Q

saponification

A

basic conditions
carboxylic acids are deprotinated and their conjugate bases form salts
ROOH+ NA+ +.OH- –> RCOO - + h2o

63
Q

amides

A

COOH deriviatives where the OH group is replaced with an amine

64
Q

lactims

A

cyclic amides

65
Q

beta lactams importance

A

form antibiotics like penicillen and its deriviatives

66
Q

ester

A

COOH deriviative where OH is replaced by OR
longer chain recieves oate ending

67
Q

is the boiling point of an ester higher or lower than a COOH

A

lower because less ability to hydrogen bond

68
Q

acid annhydrides

A

COOH derivative formed by two cooh combined,
often symmetric

69
Q

DIBAL

A

reducing agent that reduces COOH to aldehyde

70
Q

NaBH4 reaction with COOH

A

nothing

71
Q

LiAlH4 reaciton with cooh

A

primary alcohol

72
Q

decarboxylation reactions

A

when high temperature is applied to a dicarboxylic acid, one of them is lost as CO2
example PDC complex

73
Q

function of PDC complex

A

removes co2 from pyruvate to make acetyl coA

74
Q

decarboxylation steps of TCA cycle

A

isocitrate –> alpha ketogluterate
alpha ketogluterate –> succinyl coA

75
Q

cooh reaction reference

A

has great leaving group (OH) and undergoes nucleophilic substitution

76
Q

fisher esterification

A

when ROH acts as a nucleophile and attacks carbonyl of COOH
- nucleophilic substitution

77
Q

Hell-Volhard-Zelinsky halogenation

A

COOH is halogenated at the alpha carbon because of its slight acidity

78
Q

regarding the relative interconversion of COOH derivitives order them most to least reactive

A

annhydrides> esters> amides
higher reactive can be converted into lower reactive but not vice versa

79
Q

transesterification

A

when an ester reacts with a new ROH group that is different from its own and gets a new ROH substituent attatched to carbonyl carbon

80
Q

hydrolysis of amides

A

convert amide to parent cooh and amine
- break down of peptide bonds via hydrolysis

81
Q

electronic effect

A

EWG like oxygen make a carbonyl carbon more reactive
- resonance stabilizes charge and increases acidity

82
Q

amines

A

derivatives of NH3
- undergo hydrogen bonding
- higher h bonding ability than aldehyde so higher bp

83
Q

analine

A

benzene with an amine substituent

84
Q

imines

A

characterized by c=n bond and 1 c-c bond

85
Q

enamines

A

like the enol form of carbonyls with oxygen
1 c-n bond and 1 c=c bond

86
Q

relationship between enamines and imines

A

they are tautomers and interconvert

87
Q

amides

A

COOH derivative with NH replacing OH

88
Q

thiol group

A

R-SH

89
Q

sulfides/ thioethers

A

R-S-R’ group similar to ethers w oxygen

90
Q

thioester

A

R-CO-s-r’
- acetyl coA

91
Q

disulfides

A

R-S-S-R

92
Q

how does resonance affect acidity

A

increases it

93
Q

what affects impact reactivity

A

EWG, steric hinderance, strain, resonance

94
Q

how does angle strain (like in a lactam) affect reactivity

A

increases

MCAT chem (11 decks)

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