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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
LiALH4
strong reducing agent: reduces both COOH and carbonyls to alcohols
26
hemiacetals
intermediate in the formation of acetals where there is one OH group in replacement of one to the OR groups
27
aceteal
an aldehyde has 2 OR groups
28
what structure is responsible for acetals and hemiaceltas
aldehydes
29
what structure is assoicated with ketals and hemiketals
ketones
30
hemiketal
one of the 2 OR group s of. a ketal is replaced with OH
31
ketal
ketone is replaced by R1, R2, OR1, OR2
32
aldehyde
terminal carbonyl group
33
ketone
carbonyl is within the molecule
34
boiling points of aldehydes, COOH, and OH in order from lowest to highest
C=O
35
intermolecular interactions that aldehydes have which alkanes do not
dipole dipole
36
which has a higher melting point? OH or aldehyde
OH because of hydrogen bonding
37
alpha hydrogen
the hydrogen adjacent to the carbonyl carbon - important for ketone and aldehyd ereactions because of resonance stability
38
pka of aldehyde/ ketone
17-19
39
which is more acidic? aldehydes or ketones
aldehydes are slightly more acidic than ketones
40
do aldehydes and ketones act as nulceophiles or electrophiles
both
41
which part of aldehyde can act as an electrophile
the carbonyl carbon has a partial positive
42
which part of the aldehyde can act as a nucleophile
the carbanion with negative charge
43
which of the two are more reactive and why between aldehydes adn ketones
aldehydes because less steric hinderance
44
what happens when an aldehyde is reacted with PCC
nothing , weak oxidizing agent
45
strong oxiidizing agents
Na2CO2O7, K2Cr2O7, CrO3, KmNO4, Ag2O, H2O2
46
can a ketone be oxidized by a strong oxidizing agent?
no
47
NaBH4
weak reducing agent
48
reaction with water and aldehyde
nucleophile: water electrophile: carbonyl carbon product: geminal diol on carbonyl --> hydration
49
reaction with alchol and aldehyde
nucleophile: R-OH electrophile: carbonyl carbon product: hemiacetal (would be hemiketal in ketone)
50
reation with hydride (NaBH4 or LiAlH4) and aldehyde
aldehyde is reduced to a primary alochol
51
reaction with amide and aldehyde
amide is nucleophile attacks carbonyl carbon and produces imine --> enamine
52
keto form
c=o
53
enol form
c=c with oh instead of o
54
kinetically favored enolate
formed more quickly and less stable - db tends to invovle less substituted carbon because of less hinderance - low temp
55
thermodynamic enolate
db forms between carbonyl carbon and more substituted carbon , slower and more stable
56
aldol condensation
aldehydes and ketones can react with eacother - nucleophilic enolate and electrophilic carbocation - molecules join and produce an aldol (aldehyde/ketone + alcohol).
57
aldol elimination
when the aldol OH is removed via elimination to produce double bond
58
retroaldol reaction
aldol can be reversed back into aldehyde and ketone at high temperatures
59
carboxylic acid derivatives
COOH where OH is replaced by something else - amides, esters, anhydrides
60
physical properties of carboxylic acids are determined by what
ability to hydrogen bond -IMF stronger than alcohols
61
pKa of COOH
4
62
saponification
basic conditions carboxylic acids are deprotinated and their conjugate bases form salts ROOH+ NA+ +.OH- --> RCOO - + h2o
63
amides
COOH deriviatives where the OH group is replaced with an amine
64
lactims
cyclic amides
65
beta lactams importance
form antibiotics like penicillen and its deriviatives
66
ester
COOH deriviative where OH is replaced by OR longer chain recieves oate ending
67
is the boiling point of an ester higher or lower than a COOH
lower because less ability to hydrogen bond
68
acid annhydrides
COOH derivative formed by two cooh combined, often symmetric
69
DIBAL
reducing agent that reduces COOH to aldehyde
70
NaBH4 reaction with COOH
nothing
71
LiAlH4 reaciton with cooh
primary alcohol
72
decarboxylation reactions
when high temperature is applied to a dicarboxylic acid, one of them is lost as CO2 example PDC complex
73
function of PDC complex
removes co2 from pyruvate to make acetyl coA
74
decarboxylation steps of TCA cycle
isocitrate --> alpha ketogluterate alpha ketogluterate --> succinyl coA
75
cooh reaction reference
has great leaving group (OH) and undergoes nucleophilic substitution
76
fisher esterification
when ROH acts as a nucleophile and attacks carbonyl of COOH - nucleophilic substitution
77
Hell-Volhard-Zelinsky halogenation
COOH is halogenated at the alpha carbon because of its slight acidity
78
regarding the relative interconversion of COOH derivitives order them most to least reactive
annhydrides> esters> amides higher reactive can be converted into lower reactive but not vice versa
79
transesterification
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
hydrolysis of amides
convert amide to parent cooh and amine - break down of peptide bonds via hydrolysis
81
electronic effect
EWG like oxygen make a carbonyl carbon more reactive - resonance stabilizes charge and increases acidity
82
amines
derivatives of NH3 - undergo hydrogen bonding - higher h bonding ability than aldehyde so higher bp
83
analine
benzene with an amine substituent
84
imines
characterized by c=n bond and 1 c-c bond
85
enamines
like the enol form of carbonyls with oxygen 1 c-n bond and 1 c=c bond
86
relationship between enamines and imines
they are tautomers and interconvert
87
amides
COOH derivative with NH replacing OH
88
thiol group
R-SH
89
sulfides/ thioethers
R-S-R' group similar to ethers w oxygen
90
thioester
R-CO-s-r' - acetyl coA
91
disulfides
R-S-S-R
92
how does resonance affect acidity
increases it
93
what affects impact reactivity
EWG, steric hinderance, strain, resonance
94
how does angle strain (like in a lactam) affect reactivity
increases

MCAT chem (11 decks)

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