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Organic Chem > org 2 test 2 rxns > Flashcards

org 2 test 2 rxns Flashcards

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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
Q

decarboxylation

A

heat

removes COOH group

26
Q

hydrolysis of an acid chloride

A

H2O

removes Cl and adds OH forming carboxylic acid

27
Q

hydrolysis of an acid anhydride

A

anhydride= RCOOCOR
H2O
breaks apart to form 2 carboxylic acids

28
Q

hydrolysis of an ester

A

acid or base
forms carboxylate ion and alcohol in base
forms carboxylic acid and alcohol in acid

29
Q

hydrolysis of an amide

A

acid or base
forms ammonium ion and carboxylic acid in acid
forms amine and carboxylate ion in base

30
Q

hydrolysis of a nitrile

A

acid or base
forms carboxylic acid and amide–>ammonium ion in acid
forms carboxylate ion and amide–> ammonium ion in base

31
Q

acid chloride with alcohol

A

forms ester

32
Q

acid anhydride with alcohol

A

forms 1 mole of ester and 1 mole of carboxylic acid

33
Q

transesterfication

A

ester with alcohol
requires acid catalyst and excess of alcohol to drive rxn to completion
forms ester

34
Q

acid chloride with ammonia or amine

A

2 NH3
forms amide
1 NH3 forms amide other neutralizes HCl by product

35
Q

acid anhydride with ammonia or amine

A

2 NH3
forms amide
1 NH3 forms amide other neutralizes carboxylic acid by product

36
Q

ester with ammonia or primary/secondary amine

A

NH3

forms amide

37
Q

acid chloride with carboxylic acid salt

A

forms mixed anhydrides

Na+-OR

38
Q

ester with grignard reagent

A

MgBr followed by hydrolysis (H2O/HCl)
with formic ester: forms secondary alcohol
with any other ester: forms tertiary alcohol

39
Q

acid chloride with gilman reagents

A

CuLi

removes Cl and replaces with whatever is attached to CuLi

40
Q

reduction of an ester

A

LiAlH4 forms 2 alcohols

DIBALH forms 1 alcohol and 1 aldehyde

41
Q

reduction of an amide

A

LiAlH4

forms amine

42
Q

reduction of a nitrile

A

LiAlH4, ether, and H2O

gives primary amino group

43
Q

aldol reaction

A

puts aldehyde/ketone on enolate anion of another aldehyde/ketone
bond forms of carbon alpha to carbonyl
1 carbonyl reduced to alcohol

44
Q

dehydration of aldol reaction

A

acid or base

reduces alcohol group to form double bond

45
Q

claisen condensation

A

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
Q

diekmann condensation

A

intramolecular claisen condensation
molecule must have 2 ester groups
1 carbonyl attacks carbon alpha to other carbonyl

47
Q

alkylation of an enamine followed by hydrolysis

A

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
Q

acylation of enamine followed by hydrolysis

A

same as alkylation (acyl halide attacks double bond, double bond to N, hydrolysis removes N group and attaches carbonyl)

49
Q

acetoacetic ester synthesis

A

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
Q

michael reaction

A

adds nuc to C=C at the beta carbon

51
Q

robinson annulation

A

michael raction followed by intramolecular aldol reaction and dehydration
double bond formed between carbons alpha and beta to carbonyl

52
Q

conjugate addition of gilman reagents

A

adds group attached to CuLi to double bond on carbon beta to carbonyl

Organic Chem (5 decks)

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