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MCAT > ochem reactions > Flashcards

ochem reactions Flashcards

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MCAT flashcards
1
Q

what is the combustion reaction equation?

A
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2
Q

describe the three steps of free readical halogenation

A
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3
Q

what is pyrolysis

A
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4
Q

what is disproportionation

A
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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

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6
Q

What kinds of reactions do alkans undergo?

A

cumbustion

free radical halogenation

pyrolysis

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7
Q

how do you synthesize alkenes

A

elimination reaction

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8
Q

what kinds of reactants undergo elimination to get alkenes

A

alcohols and alkyl halides

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9
Q

catalytic hydrogenation of alkenes

A
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10
Q

addition of HX to akene

A
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11
Q

addition of X2 to an alkene

A

anti addition

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12
Q

adding water to an akene

A
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13
Q

free radical additions to alkene

A
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14
Q

hydroboration of alkene

A
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15
Q

reagent used to oxidize alkenes

A

potassium permanganate (KMnO4) either hot or cold.

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16
Q

oxidizing alkene with cold dilute KMnO4

A
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17
Q

oxidation of alkene with hot basic solution of KMnO4

A

makes carboxylic acids

terminal alkenes become ketone and co2

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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

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19
Q

how can you use ozonolysis to synthesize alcohols

A

reduce ketone /aldehyde products with mild reducing agent such as NaBH4 or LiAlH4

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20
Q

cycloalkene plus MCPBA

A

SYN addition

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21
Q

polymerization

A
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22
Q

two ways to synthesize alkynes

A

two rounds of elimination of geminal or vicinal dihalide

using an acetylide ion

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23
Q

snthesize alkyne with a dihalide

A
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24
Q

using an acetylide ion to form an alkyne

A
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25
Q

how to reduce alkyne and get cis isomer

A

H2 and lindlers catalyst

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26
Q

how to reduce alkyne and get trans isomer

A

use sodium in liquid ammonia below -33 degrees C. mechanism=free radical

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27
Q

adding 1 or 2 equivalent of Br2 to an alkyne

A
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28
Q

describe free radical addition to alkynes

A

anti markovnikov orientation. reaction product is usually the trans isomer

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29
Q

what product do you get from the hydroboration of an alkyne

A

syn addition

produces cis alkenes

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30
Q

hydroboration of terminal alkyne

A
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31
Q

ozonolysis of alkynes

A

acts just like hot basic KMnO4

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32
Q

halogenation of benzene

A
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33
Q

sulfonation of benzene

A
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34
Q

nitration of benzene

A
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35
Q

how to add -COCH3 to benzene

A

Acylation (Friedel Crafts Reactions

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36
Q

substituent effects: activator

A

donate electron density

directs new substituents to ortho and para positions

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37
Q

substituent effects: deactivator

A

electron withdrawing

meta position

exceptions: halogens are deactivating, but direct to the ortho and para positions

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38
Q

catalytic reduction of benzene rings

A

only under vigorous conditions: elevated temp and pressure

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39
Q

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

A

LiAlH4 – strong –reduces everything

NaBH4 – weak – reduces aldehydes, ketones, acyl chlorides, but does not reduce esters, carboxylic acids, or amines

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40
Q

phenol synthesis via hydrolysis of diazonium salt

A
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41
Q

elimination rxn with alcohol

A
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42
Q

what is required for a substitution reaction with an alcohol

A

OH is a poor leaving group, must be protonated for SN1 or tosylated for SN2

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43
Q

substitution with tosylated alcohol

A
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44
Q

conversion of an alcohol to an alkyl halide

A
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45
Q

oxidation of alcohols with PCC (what is different about PCC?)

A

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

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46
Q

alcohol + Na2Cr2O7 (what kind of reagent is Na2Cr2O7)

A

strong oxidzing agent- will fully oxidize primary alcohols to carboxylic acids (secondary to ketones)

47
Q

what is an even stronger oxidizing agent than Dichromate salt?

A

Chromium trioxide (CrO3) also called Jones reagent/jones oxidation.

48
Q

what products do you get from oxidizing phenols?

A

quinones

49
Q

williamson ether synthesis

A
50
Q

williamson ether synthesis with phenol

A
51
Q

synthesis of cyclic ether via sn2

A
52
Q

synthesis of cyclic ether with peroxy acid (what is peroxy acid)

A

proxy acid: general formula (RCOOH

example: mcpba

53
Q

cleavage reaction–what conditions are required?

A

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
Q

epoxide opening (two types)

A

acid-catalyzed

base catalyzed

55
Q

enolization

what are the two isomers called?

A

two isomers are called tautomers

56
Q

michael addition

A
57
Q

addition raction to carbonyl to make alcohol

A
58
Q

hydration rxn of carbonyl

A
59
Q

addition of one equivalent of alcohol to aldehyde or ketone

A

heiacetal or hemiketal formation

60
Q

addition of two equivalents of alcohol to aldehyde or ketone

A

acetal and ketal formation

61
Q

addition of cyanide to carbonyl

A
62
Q

condensation reaction with ammonia derivative. what is a condensation reaction?

A

a condensation reaction is a reaction in which water is lost between two molecules

63
Q

nucleophilic additions of ammonia derivatives to carbonyls

NH3,

H2NOH

H2NNH2

H2NNHCONH2

A
64
Q

aldol formation

A
65
Q

aldol condensation

A
66
Q

wittig reaction

A
67
Q

wolff-kishner reduction

A
68
Q

clemmensen reduction

A
69
Q

formation of carboxylic acids using organometallic reagents

A
70
Q

synthesis of carboxylic acid via hydrolysis of nitriles

A
71
Q

nucleophlic acyl substitution to carboxylic acid

A

same as substitution with carbonyl

72
Q

reduction of carboxylic acid

A
73
Q

formation of an ester from carboxylic acid and alcohol

A
74
Q

acyl halide formation from carboxylic acid. what reagent do you react with the carboxylic acid?

A

thionyl chloride (SOCl2)

75
Q

decarboxylation reaction, what is required for spontaneous decarboxylation?

A

requires heat

76
Q

hydrolysis of acyl chloride

A
77
Q

conversion of acyl chloride into ester

A
78
Q

conversion of acyl halides into amides

A
79
Q

friedel crafts acylation

A
80
Q

conversion of acyl halide to corresponding aldehyde. what kind of reagent?

A

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
Q

synthesis of anhydrides starting with carboxylic acid

A

condensation of carboxylic acid

82
Q

synthesis of anhydride from acid chloride

A

acid chloride plus carboxylate ion

83
Q

intramolecular anhydride formation

A
84
Q

hydrolysis of anhydride

A
85
Q

conversion of anhydrider to amides

A
86
Q

formation of ammonium carboxylate from anhydride

A
87
Q

formation of an ester from anhydride

A
88
Q

friedel crafts acylation using anhydride

A
89
Q

hydrolysis of an amide

A
90
Q

hoffman rearangement

A

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
Q

reduction of amide

A
92
Q

creations of esters from carboxylic acids

A
93
Q

hydrolysis of esters

A
94
Q

what is saponification and acidification

A

the process by which fats are hydrolized under basic conditions to produce soaps–acidification of soap regenerates fatty acids

95
Q

creating an amide from an ester

A
96
Q

transesterification

A
97
Q

grignard addition to esters

A
98
Q

claisen condesnation

A
99
Q

ester reduction.

A

cannot be reduced with weak reducing agents like nabh4

100
Q

what are phosphate esters

A
101
Q

alkylation of ammonia (direct alkylation)

A
102
Q

gabriel synthesis: what is it used to accomplish?

A

converts primary alkyl halide to primary amine

103
Q

reduction of nitro group

A
104
Q

reduction of nitriles

A
105
Q

formation of amine from an imine

A
106
Q

reduction of amide to amine

A
107
Q

exhaustive methylation

A
108
Q

glucose esterification

A
109
Q

oxidation of monosaccharides. what oxidizing agents do you use

A

aldoses can be oxidized to aldonic acids by tollens’s or benedicts reagents

110
Q

glycosidic linkage formation

A

hemiacetal or hemiaketal sugrs react with alcohol under acidic conditions and form acetals or ketals (carbon with 2 -OR groups)

111
Q

disacchride formatin

A

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
Q

alpha vs beta glycosidic linkage

A
113
Q

peptide bond formation and hydrolysis

A
114
Q

tiration of an amino acid

A
  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

MCAT (17 decks)

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