org 2 test 2 rxns Flashcards

(52 cards)

1
Q

grignard reagents with carbonyl

A

-mgbr
carbonyl–>alcohol
adds whatever is attached to mgbr

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2
Q

organolithium with carbonyl

A

-culi
carbonyl–>alcohol
adds whatever is attached to culi

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3
Q

carbonyl with anion of terminal alkyne

A

carbonyl–>alcohol

adds alkyne

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4
Q

carbonyl with cyanohydrin

A

HCN
carbonyl–>alcohol
adds c—n

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5
Q

wittig reaction

A

Ph3P-CH2

carbonyl to alkene (R=CH2)

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6
Q

horner-emmons-wadsworth modification of wittig reaction

A

takes off phosphate group

adds internal alkene (where carbonyl group was)

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7
Q

hydration of carbonyl

A

h2o

carbonyl–>alcohol

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8
Q

hemiacetal formation

A

addition of alcohol

catalyzed by acid or base

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9
Q

acetal formation

A

addition of alcohol
catalyzed by acid or base
2 equivalents

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10
Q

formation of imines

A

addition of ammonia and its derivatives

carbonyl–> R=NR’

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11
Q

formation of enamines

A

addition of secondary amines
carbonyl leaves and double bond formed 1 bond away
bond between N and where carbonyl was

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12
Q

hydrazine and its derivatives

A

H2N=NH2

carbonyl–> R=N

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13
Q

aldehyde to carboxylic acid

A

H2CrO4
KMnO4
Ag2O

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14
Q

metal hydride reduction of carbonyls

A

carbonyl–>alcohol

NaBH4 and H2O

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15
Q

catalytic reduction of carbonyls

A

carbonyl–> alcohol

H2 and metal

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16
Q

reductive amination

A

CH3NH2 and reducing agent

carbonyl–> R-NHCH3

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17
Q

clemmensen reduction

A

ZnHg and HCl

removes carbonyl

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18
Q

wolff-kishner reduction

A

H2NNH2
removes carbonyl
N2 and H2O byproduct

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19
Q

halogenation at alpha carbon of carbonyl

A

adds halogen to carbon alpha to carbonyl

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20
Q

carbonation of grignard reagent

A

CO2 and HCl/H2O
MgBr –> COOH
formation of carboxylic acid

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21
Q

lithium aluminum hydride

A

LiAlH4
removes carbonyl from carboxylic acid
leaves alcohol

22
Q

fischer esterification

A

carboxylic acid + alcohol in presence of acid catalyst

gives ester

23
Q

carboxylic acid with diazomethane

A

CH2N2

carboxylic acid to methyl ester

24
Q

carboxylic acid to acid halide

A

SOCl2 or PBr3

replaces OH with halide

25
decarboxylation
heat | removes COOH group
26
hydrolysis of an acid chloride
H2O | removes Cl and adds OH forming carboxylic acid
27
hydrolysis of an acid anhydride
anhydride= RCOOCOR H2O breaks apart to form 2 carboxylic acids
28
hydrolysis of an ester
acid or base forms carboxylate ion and alcohol in base forms carboxylic acid and alcohol in acid
29
hydrolysis of an amide
acid or base forms ammonium ion and carboxylic acid in acid forms amine and carboxylate ion in base
30
hydrolysis of a nitrile
acid or base forms carboxylic acid and amide-->ammonium ion in acid forms carboxylate ion and amide--> ammonium ion in base
31
acid chloride with alcohol
forms ester
32
acid anhydride with alcohol
forms 1 mole of ester and 1 mole of carboxylic acid
33
transesterfication
ester with alcohol requires acid catalyst and excess of alcohol to drive rxn to completion forms ester
34
acid chloride with ammonia or amine
2 NH3 forms amide 1 NH3 forms amide other neutralizes HCl by product
35
acid anhydride with ammonia or amine
2 NH3 forms amide 1 NH3 forms amide other neutralizes carboxylic acid by product
36
ester with ammonia or primary/secondary amine
NH3 | forms amide
37
acid chloride with carboxylic acid salt
forms mixed anhydrides | Na+-OR
38
ester with grignard reagent
MgBr followed by hydrolysis (H2O/HCl) with formic ester: forms secondary alcohol with any other ester: forms tertiary alcohol
39
acid chloride with gilman reagents
CuLi | removes Cl and replaces with whatever is attached to CuLi
40
reduction of an ester
LiAlH4 forms 2 alcohols | DIBALH forms 1 alcohol and 1 aldehyde
41
reduction of an amide
LiAlH4 | forms amine
42
reduction of a nitrile
LiAlH4, ether, and H2O | gives primary amino group
43
aldol reaction
puts aldehyde/ketone on enolate anion of another aldehyde/ketone bond forms of carbon alpha to carbonyl 1 carbonyl reduced to alcohol
44
dehydration of aldol reaction
acid or base | reduces alcohol group to form double bond
45
claisen condensation
forms beta-ketoester nucleophilic acyl substitution enolate anion of 1 ester attacks another ester and forms bond on carbon alpha to carbonyl 1 hydroxy group lost
46
diekmann condensation
intramolecular claisen condensation molecule must have 2 ester groups 1 carbonyl attacks carbon alpha to other carbonyl
47
alkylation of an enamine followed by hydrolysis
group attached to alkyl halide attacks double bond breaking it and forming double bond to N hydrolysis takes off N group and adds carbonyl
48
acylation of enamine followed by hydrolysis
same as alkylation (acyl halide attacks double bond, double bond to N, hydrolysis removes N group and attaches carbonyl)
49
acetoacetic ester synthesis
EtO-Na+, alkyl halide, NaOH/H2O, HCl/H2O, heat | puts 2 molecules together forming monosubstituted and disubstituted acetic acids (removes COOEt-->COOH on end)
50
michael reaction
adds nuc to C=C at the beta carbon
51
robinson annulation
michael raction followed by intramolecular aldol reaction and dehydration double bond formed between carbons alpha and beta to carbonyl
52
conjugate addition of gilman reagents
adds group attached to CuLi to double bond on carbon beta to carbonyl