Retrons

Question 1

Primary Alkyl Bromides

Answer 1

Radical Mediated addition of HBr to alkenes

Question 2

Secondary and Tertiary Alkyl Bromides and Chlorides

Answer 2

Ionic addition of HBr and HCl to alkenes

Question 3

Secondary vinyl bromides

Answer 3

Ionic addition of HBr and HCl to terminal alkynes

Question 4

1,2-Dibromides

Answer 4

Addition of Bromide to Alkenes

Question 5

E-1,2 Dibromoalkenes

Answer 5

Addition of Bromide to Alkynes

Question 6

Primary and secondary bromides with hydroxyl group on adjacent carbon

Answer 6

bromohydroxylation

Question 7

Epoxides

Answer 7

Epoxidation

Question 8

Secondary and tertiary alcohols with bromide on adjacent carbon

Answer 8

bromohydroxylation

Question 9

Secondary and tertiary alcohols

Answer 9

Acid catalyzed hydration of alkenes

Question 10

Primary and secondary alcohols

Answer 10

hydroboration of alkenes

Question 11

Cis 1,2 diols

Answer 11

Dihydroxylation of alkenes

Question 12

Ketones 6 ways

Answer 12

Ozonolysis of alkenes, acid-catalyzed hydration of internal alkynes, hydroboration of internal alkynes
Swern Oxidation of secondary alcohols
Oxidation with PCC of secondary alcohols
Hydrolysis of acetals

Question 13

Aldehydes 4 ways

Answer 13

Ozonolysis, hydroboration of terminal alkynes, swern oxidation of primary alcohols, oxidation with pcc of primary alcohols

Question 14

Alkynes

Answer 14

Alkylation of metal acetylides

Question 15

Cis Alkenes

Answer 15

Lindlar catalyst hydrogenation of internal alkynes

Question 16

Trans Alkenes

Answer 16

Metal-Ammonia Reduction of Internal Alkynes

Question 17

Monosubstituted Alkenes

Answer 17

Lindlar catalyst hydrogenation of terminal alkynes

Question 18

Alkanes

Answer 18

Hydrogenation of alkynes and alkanes

Question 19

Terminal and disubstituted alkenes

Answer 19

E2 reactions of halides and sulfonates

Question 20

Cyclic alkenes

Answer 20

E2 reactions of halides and sulfonates

Question 21

Mono, di, tri alkenes

Answer 21

Wittig reaction of aldehydes and ketones

Question 22

Propargylic alcohols

Answer 22

Lithium Acetylides added to carbonyls

Question 23

Primary and secondary alkyl halides from alcohols

Answer 23

Add sulfonates

Question 24

Alcohols

Answer 24

LiAlH4 and NaBH4 reduction of carbonyls; Adding grignard reagents and alkyllithiums to carbonyls

Question 25

Primary amines

Answer 25

SN2 of primary alkyl halides with excess ammonia or with sodium azide before reduction

Question 26

Secondary amines

Answer 26

SN2 of primary alkyl halides with excess alkane

Question 27

Nitriles 2 ways

Answer 27

SN2 with NaCN, forming cyanohydrins with NaCN

Question 28

Ethers

Answer 28

Williamson ether synthesis

Question 29

Thiol

Answer 29

SN2 reaction of sulfonates and halides with NaSH

Question 30

Thioethers

Answer 30

unsymmetric formed by sn2 with thiol as nucleophile
symmetric formed by sn2 with Na2S forming an S-2 nucleophile

Question 31

Alpha bromo ketones

Answer 31

acid catalyzed enolization + Br2

Question 32

Amines

Answer 32

reductive amination, reduction of amides with LiAlH4, reduction of nitriles with LiAlH4

Question 33

Acetals

Answer 33

Acid catalyzed addition of alcohol to hemiacetal

Question 34

Imines and Enamines

Answer 34

Acid catalyzed NH3 addition to carbonyl with dean stark

Question 35

Carboxylic acids 4 ways

Answer 35

Oxidation of aldehydes and primary alcohols with H2CrO4 in H2SO4 and water
Carboxylation of grignard reagents with CO2
Saponification of esters
H2SO4 hydrolysis of amides

Question 36

Esters 2 ways

Answer 36

Acyl chloride + alcohol with Pyridine
Carboxylic acid + alcohol with TsOH

Question 37

Amides

Answer 37

Acyl chloride + amines with pyridine

Question 38

Acyl chloride

Answer 38

Carboxylic acid + SOCl2 or (COCl)2