org 2 test 2 rxns

Question 1

grignard reagents with carbonyl

Answer 1

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

Question 2

organolithium with carbonyl

Answer 2

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

Question 3

carbonyl with anion of terminal alkyne

Answer 3

carbonyl–>alcohol

adds alkyne

Question 4

carbonyl with cyanohydrin

Answer 4

HCN
carbonyl–>alcohol
adds c—n

Question 5

wittig reaction

Answer 5

Ph3P-CH2

carbonyl to alkene (R=CH2)

Question 6

horner-emmons-wadsworth modification of wittig reaction

Answer 6

takes off phosphate group

adds internal alkene (where carbonyl group was)

Question 7

hydration of carbonyl

Answer 7

h2o

carbonyl–>alcohol

Question 8

hemiacetal formation

Answer 8

addition of alcohol

catalyzed by acid or base

Question 9

acetal formation

Answer 9

addition of alcohol
catalyzed by acid or base
2 equivalents

Question 10

formation of imines

Answer 10

addition of ammonia and its derivatives

carbonyl–> R=NR’

Question 11

formation of enamines

Answer 11

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

Question 12

hydrazine and its derivatives

Answer 12

H2N=NH2

carbonyl–> R=N

Question 13

aldehyde to carboxylic acid

Answer 13

H2CrO4
KMnO4
Ag2O

Question 14

metal hydride reduction of carbonyls

Answer 14

carbonyl–>alcohol

NaBH4 and H2O

Question 15

catalytic reduction of carbonyls

Answer 15

carbonyl–> alcohol

H2 and metal

Question 16

reductive amination

Answer 16

CH3NH2 and reducing agent

carbonyl–> R-NHCH3

Question 17

clemmensen reduction

Answer 17

ZnHg and HCl

removes carbonyl

Question 18

wolff-kishner reduction

Answer 18

H2NNH2
removes carbonyl
N2 and H2O byproduct

Question 19

halogenation at alpha carbon of carbonyl

Answer 19

adds halogen to carbon alpha to carbonyl

Question 20

carbonation of grignard reagent

Answer 20

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

Question 21

lithium aluminum hydride

Answer 21

LiAlH4
removes carbonyl from carboxylic acid
leaves alcohol

Question 22

fischer esterification

Answer 22

carboxylic acid + alcohol in presence of acid catalyst

gives ester

Question 23

carboxylic acid with diazomethane

Answer 23

CH2N2

carboxylic acid to methyl ester

Question 24

carboxylic acid to acid halide

Answer 24

SOCl2 or PBr3

replaces OH with halide

Question 25

decarboxylation

Answer 25

heat | removes COOH group

Question 26

hydrolysis of an acid chloride

Answer 26

H2O | removes Cl and adds OH forming carboxylic acid

Question 27

hydrolysis of an acid anhydride

Answer 27

anhydride= RCOOCOR H2O breaks apart to form 2 carboxylic acids

Question 28

hydrolysis of an ester

Answer 28

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

Question 29

hydrolysis of an amide

Answer 29

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

Question 30

hydrolysis of a nitrile

Answer 30

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

Question 31

acid chloride with alcohol

Answer 31

forms ester

Question 32

acid anhydride with alcohol

Answer 32

forms 1 mole of ester and 1 mole of carboxylic acid

Question 33

transesterfication

Answer 33

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

Question 34

acid chloride with ammonia or amine

Answer 34

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

Question 35

acid anhydride with ammonia or amine

Answer 35

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

Question 36

ester with ammonia or primary/secondary amine

Answer 36

NH3 | forms amide

Question 37

acid chloride with carboxylic acid salt

Answer 37

forms mixed anhydrides | Na+-OR

Question 38

ester with grignard reagent

Answer 38

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

Question 39

acid chloride with gilman reagents

Answer 39

CuLi | removes Cl and replaces with whatever is attached to CuLi

Question 40

reduction of an ester

Answer 40

LiAlH4 forms 2 alcohols | DIBALH forms 1 alcohol and 1 aldehyde

Question 41

reduction of an amide

Answer 41

LiAlH4 | forms amine

Question 42

reduction of a nitrile

Answer 42

LiAlH4, ether, and H2O | gives primary amino group

Question 43

aldol reaction

Answer 43

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

Question 44

dehydration of aldol reaction

Answer 44

acid or base | reduces alcohol group to form double bond

Question 45

claisen condensation

Answer 45

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

Question 46

diekmann condensation

Answer 46

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

Question 47

alkylation of an enamine followed by hydrolysis

Answer 47

group attached to alkyl halide attacks double bond breaking it and forming double bond to N hydrolysis takes off N group and adds carbonyl

Question 48

acylation of enamine followed by hydrolysis

Answer 48

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

Question 49

acetoacetic ester synthesis

Answer 49

EtO-Na+, alkyl halide, NaOH/H2O, HCl/H2O, heat | puts 2 molecules together forming monosubstituted and disubstituted acetic acids (removes COOEt-->COOH on end)

Question 50

michael reaction

Answer 50

adds nuc to C=C at the beta carbon

Question 51

robinson annulation

Answer 51

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

Question 52

conjugate addition of gilman reagents

Answer 52

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