ochem reactions Flashcards
(114 cards)
1
Q
what is the combustion reaction equation?
A
2
Q
describe the three steps of free readical halogenation
A
3
Q
what is pyrolysis
A
4
Q
what is disproportionation
A
5
Q
what is the difference between disproportionation and pyrolysis
A
disproportionation is when a radical transfers a hydrogen atom to another radical producing an alkane and an alkene
6
Q
What kinds of reactions do alkans undergo?
A
cumbustion
free radical halogenation
pyrolysis
7
Q
how do you synthesize alkenes
A
elimination reaction
8
Q
what kinds of reactants undergo elimination to get alkenes
A
alcohols and alkyl halides
9
Q
catalytic hydrogenation of alkenes
A
10
Q
addition of HX to akene
A
11
Q
addition of X2 to an alkene
A
anti addition
12
Q
adding water to an akene
A
13
Q
free radical additions to alkene
A
14
Q
hydroboration of alkene
A
15
Q
reagent used to oxidize alkenes
A
potassium permanganate (KMnO4) either hot or cold.
16
Q
oxidizing alkene with cold dilute KMnO4
A
17
Q
oxidation of alkene with hot basic solution of KMnO4
A
makes carboxylic acids
terminal alkenes become ketone and co2
18
Q
Ozonolysis of alkene
A
makes aldehydes and ketones under reducing condtions (Zn/H+ or (CH3)2S)
under oxidizing conditions (H2O2) has same products as hot KMnO4
19
Q
how can you use ozonolysis to synthesize alcohols
A
reduce ketone /aldehyde products with mild reducing agent such as NaBH4 or LiAlH4
20
Q
cycloalkene plus MCPBA
A
SYN addition
21
Q
polymerization
A
22
Q
two ways to synthesize alkynes
A
two rounds of elimination of geminal or vicinal dihalide
using an acetylide ion
23
Q
snthesize alkyne with a dihalide
A
24
Q
using an acetylide ion to form an alkyne
A
25
how to reduce alkyne and get cis isomer
H2 and lindlers catalyst
26
how to reduce alkyne and get trans isomer
use sodium in liquid ammonia below -33 degrees C. mechanism=free radical
27
adding 1 or 2 equivalent of Br2 to an alkyne
28
describe free radical addition to alkynes
anti markovnikov orientation. reaction product is usually the trans isomer
29
what product do you get from the hydroboration of an alkyne
syn addition
produces cis alkenes
30
hydroboration of terminal alkyne
31
ozonolysis of alkynes
acts just like hot basic KMnO4
32
halogenation of benzene
33
sulfonation of benzene
34
nitration of benzene
35
how to add -COCH3 to benzene
Acylation (Friedel Crafts Reactions
36
substituent effects: activator
donate electron density
directs new substituents to ortho and para positions
37
substituent effects: deactivator
electron withdrawing
meta position
exceptions: halogens are deactivating, but direct to the ortho and para positions
38
catalytic reduction of benzene rings
only under vigorous conditions: elevated temp and pressure
39
reduction reactions to make alcohols
what is an example of a strong reducing agent and what is an example of a weak reducing agent, and what do they reduce
LiAlH4 -- strong --reduces everything
NaBH4 -- weak -- reduces aldehydes, ketones, acyl chlorides, but does not reduce esters, carboxylic acids, or amines
40
phenol synthesis via hydrolysis of diazonium salt
41
elimination rxn with alcohol
42
what is required for a substitution reaction with an alcohol
OH is a poor leaving group, must be protonated for SN1 or tosylated for SN2
43
substitution with tosylated alcohol
44
conversion of an alcohol to an alkyl halide
45
oxidation of alcohols with PCC (what is different about PCC?)
PCC is a mild oxidant and is able to partially oxidizes primary alcohols.--stops after primary alcohol has become an aldehyde
behaves normally with secondary alcohols
46
alcohol + Na2Cr2O7 (what kind of reagent is Na2Cr2O7)
strong oxidzing agent- will fully oxidize primary alcohols to carboxylic acids (secondary to ketones)
47
what is an even stronger oxidizing agent than Dichromate salt?
Chromium trioxide (CrO3) also called Jones reagent/jones oxidation.
48
what products do you get from oxidizing phenols?
quinones
49
williamson ether synthesis
50
williamson ether synthesis with phenol
51
synthesis of cyclic ether via sn2
52
synthesis of cyclic ether with peroxy acid (what is peroxy acid)
proxy acid: general formula (RCOOH
example: mcpba
53
cleavage reaction--what conditions are required?
vigorous conditions==high temp with HBr or HI
SN1 or SN2 reaction
alcohol products usually react with a 2nd molecule of hydrogen halide to produce alkyl halide
54
epoxide opening (two types)
acid-catalyzed
base catalyzed
55
enolization
what are the two isomers called?
two isomers are called tautomers
56
michael addition
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addition raction to carbonyl to make alcohol
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hydration rxn of carbonyl
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addition of one equivalent of alcohol to aldehyde or ketone
heiacetal or hemiketal formation
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addition of two equivalents of alcohol to aldehyde or ketone
acetal and ketal formation
61
addition of cyanide to carbonyl
62
condensation reaction with ammonia derivative. what is a condensation reaction?
a condensation reaction is a reaction in which water is lost between two molecules
63
nucleophilic additions of ammonia derivatives to carbonyls
NH3,
H2NOH
H2NNH2
H2NNHCONH2
64
aldol formation
65
aldol condensation
66
wittig reaction
67
wolff-kishner reduction
68
clemmensen reduction
69
formation of carboxylic acids using organometallic reagents
70
synthesis of carboxylic acid via hydrolysis of nitriles
71
nucleophlic acyl substitution to carboxylic acid
same as substitution with carbonyl
72
reduction of carboxylic acid
73
formation of an ester from carboxylic acid and alcohol
74
acyl halide formation from carboxylic acid. what reagent do you react with the carboxylic acid?
thionyl chloride (SOCl2)
75
decarboxylation reaction, what is required for spontaneous decarboxylation?
requires heat
76
hydrolysis of acyl chloride
77
conversion of acyl chloride into ester
78
conversion of acyl halides into amides
79
friedel crafts acylation
80
conversion of acyl halide to corresponding aldehyde. what kind of reagent?
bulky reducing agent
LiAl(O-R)3H (only has one hydride to transfer. this prevents reducing agent from reducing all the way to an alcohol)
81
synthesis of anhydrides starting with carboxylic acid
condensation of carboxylic acid
82
synthesis of anhydride from acid chloride
acid chloride plus carboxylate ion
83
intramolecular anhydride formation
84
hydrolysis of anhydride
85
conversion of anhydrider to amides
86
formation of ammonium carboxylate from anhydride
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formation of an ester from anhydride
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friedel crafts acylation using anhydride
89
hydrolysis of an amide
90
hoffman rearangement
an amide is exposed to br2 and haoh which formes a nitrene results in the rearrangement of the R group bound to the carbonyl and the formation of isocyanate; isocyanate is then hydrolied to form co2 and an amine
91
reduction of amide
92
creations of esters from carboxylic acids
93
hydrolysis of esters
94
what is saponification and acidification
the process by which fats are hydrolized under basic conditions to produce soaps--acidification of soap regenerates fatty acids
95
creating an amide from an ester
96
transesterification
97
grignard addition to esters
98
claisen condesnation
99
ester reduction.
cannot be reduced with weak reducing agents like nabh4
100
what are phosphate esters
101
alkylation of ammonia (direct alkylation)
102
gabriel synthesis: what is it used to accomplish?
converts primary alkyl halide to primary amine
103
reduction of nitro group
104
reduction of nitriles
105
formation of amine from an imine
106
reduction of amide to amine
107
exhaustive methylation
108
glucose esterification
109
oxidation of monosaccharides. what oxidizing agents do you use
aldoses can be oxidized to aldonic acids by tollens's or benedicts reagents
110
glycosidic linkage formation
hemiacetal or hemiaketal sugrs react with alcohol under acidic conditions and form acetals or ketals (carbon with 2 -OR groups)
111
disacchride formatin
the hydroxyl on the anomeric rbon reat with he hydroxyl of another sugar to form acetals or ketals with1,2 1,4 1,6glycosidic linkages
112
alpha vs beta glycosidic linkage
113
peptide bond formation and hydrolysis
114
tiration of an amino acid
1. when adding base, the carboxyl groups lose their protons first; after all of the carboxyl groups are fully deprotonated, the amino groups start to lose thir acidic protons
2. two moles of base must be added to deprotonate one mole of most amino acids. the first mole deprotonates the arboxyl group, whereas the second deprotonates the amino group
3. the buffering capacity of the amino acid is greatest at or near the pH of the two dissocition constants pka1 and pka2. its buffering capacity is minimal and the graph appears as a vertical line
4. some amino acids contain acidic or basic side chains to find the pI of these amino acids, simpling average the two acidic pkas if the side chain is acidic or the two basic pakas if the side chain is basic
5. it is possible to perform the itriation in reverse from alkaline pH to acidic pH with the addition of acid; in that case the sequence of events is reversed
