organic synthesis routes

Question 1

how can an acyl chloride become a secondary amide

Answer 1

react with a primary amine via nucleophilic addition elimination

Question 2

how can an acyl chloride form a primary amide

Answer 2

by reaction with ammonia via nucleophilic addition elimination

Question 3

how can an acyl chloride become a carboxylic acid

Answer 3

reaction with water via hydrolysis

Question 4

how can an ester form a carboxylic acid

Answer 4

using dilute acid, via acid hydrolysis

Question 5

how can an ester form a carboxylate salt and alcohol

Answer 5

reaction with NaOH via alkaline hydrolysis

Question 6

how can an aldehyde form a hydroxynitrile

Answer 6

reaction with NaCN and H+ via nucleophilic addition

Question 7

how can a nitrile form a carboxylic acid

Answer 7

reaction with H2O and HCl (dilute HCl) via hydrolysis

Question 8

how can an aldehyde become a primary alcohol

Answer 8

reaction with NaBH4 via reduction

Question 9

how can a ketone become a secondary alcohol

Answer 9

reaction with NaBH4 via reduction

Question 10

how does phenylethanone become 1-phenylethanol

Answer 10

react with NaBH4 via reduction

Question 11

how does benzene become phenylethanone

Answer 11

react with CH3COCl and AlCl3 via electrophilic substitution/acylation

Question 12

how does aminobenzene become 2,4,6-tribromoaminobenzene

Answer 12

react with bromine via electrophilic substitution

Question 13

how does nitrobenzene become aminobenzene

Answer 13

react with Sn and conc. HCl via reduction

Question 14

how does benzene become nitrobenzene

Answer 14

react with conc HNO3 and conc H2SO4 via electrophilic substitution/nitration

Question 15

how does benzene become methylbenzene

Answer 15

react with CH3Cl and AlCl3 via electrophilic substitution/alkylation

Question 16

what forms when an acid anhydride reacts with an alcohol

Answer 16

an ester and carboxylic acid!!!

Question 17

how can a haloalkane form a nitrile

Answer 17

react haloalkane with CN- (NaCN or KCN) and alcohol

Question 18

what is a dimer

Answer 18

a compound made up of two of the same molecule

Question 19

what are the ways to make esters

Answer 19

alcohol + carboxylic acid
alcohol + acid anhydride
alcohol + acyl chloride

Question 20

how can an acid anydride react

Answer 20

heat with alcohol to form an ester and carboxylic acid that can be separated using fractional distillation

Question 21

what is an acid anydride and how is it made

Answer 21

it is made from 2 carboxylic acid molecules

Question 22

when do you have to use LiAlH4 and a dilute acid to form an amide from a nitrile

Answer 22

if there’s also a C=C in the molecule that you don’t want to hydrogenate right now

Question 23

how do you name an acid anhydride

Answer 23

if symmetrical: name of carboxylic acid, - acid, + anhydride

if asymmetrical: name of carboxylic acid 1 -acid, name of carboxylic acid 2 - acid
put in alphabetic order + anhydrides

Question 24

what happens when you do acid hydrolysis of an ester

Answer 24

form the carboxylic acid and alcohol that make it up

Question 25

what happens when you do alkaline hydrolysis of an ester

Answer 25

alcohol and carboxylate (carboxylic acid without the H, so O-)

Question 26

what forms when a ketone reacts with NaCN/H+

Answer 26

hydroxynitrile