Organic Reactions

Front 1

Alkane > Haloalkane

Back 1

X2 & UV Light and/or heat

*alkanes are saturated so cannot take in HX but will produce it*

Front 2

Alkene > Haloalkane

Back 2

HX or X2 (shake)(room temp)

*is unsaturated so can either take double X or an X and an H*

Front 3

Alkene > Alcohol

Back 3

Dilute H2SO4

*water then conc H2SO4 then water*

Front 4

Haloalkane > Alcohol

Back 4

KOH(aq) under reflux

*OH is a nucleophile and boots out the X, replacing X with itself*

Front 5

Haloalkane > Alkene

Back 5

KOH(alc) under reflux

*dont want OH nucleophilic substitution so alcohol will help us keep it clean*

Front 6

Alcohol > Haloalkane

Back 6

SOCl2 (or PCl3, PCl5)

*O is lost to SO2 and one H is lost to HCl. Both evaporate and the Cl joins the molecule*

Front 7

Carboxylic acid > Acid chloride

Back 7

SOCl2 (or PCl3, PCl5)

*O is lost to SO2 and one H is lost to HCl. Both evaporate and the Cl joins the molecule*

Front 8

Alcohol > Ester

Back 8

Heat with carboxylic acid and conc H2SO4

*H2SO4 acts as a dehydrating agent, reacting with the product H2O to keep the reversible reaction on the product ester side*

Front 9

Carboxylic acid > Ester

Back 9

Heat with alcohol and conc H2SO4

*H2SO4 acts as a dehydrating agent, reacting with the product H2O to keep the reversible reaction on the product ester side*

Front 10

Primary alcohol > Aldehyde

Back 10

Acidified oxidant (heat and distill off)

*aldehyde cant hydrogen bond so it evaporates first and you must distill to keep it reacting further to become a carbo*

Front 11

Primary alcohol > Carboxylic acid

Back 11

Acidified oxidant (heat under reflux)

*let the aldehyde fall back down and take the reaction to completion*

Front 12

Secondary alcohol > Ketone

Back 12

Acidified oxidant (heat under reflux)

*ketone because two degree alcohol groups arent on terminal carbons*

Front 13

Ester > Alcohol & Carboxylic acid

Back 13

Heat with H+/H2O

*acid because ester is nonpolar and doesnt react with water, also alkali produces coo-na+*

Front 14

Ester > Alcohol & COO-Na+

Back 14

Heat with NaOH(aq)

*base because ester is nonpolar and doesnt react with water*

Front 15

Ester > Alcohol & Amide

Back 15

Heat with NH3(alc)

*slow reaction, better to use acid chloride and alcoholic ammonia*

Front 16

Carboxylic acid > 2° Amide

Back 16

Heat with amine

*simple condensation, also basis for polyamides*

Front 17

Alkene > Alkane

Back 17

Heat with H2 (Pt or Ni)

*just adding Hs I guess*

Front 18

Acid chloride > Amide

Back 18

NH3(alc)

*lose an HCl, left with NH2*

Front 19

Acid chloride > Carboxylic acid

Back 19

Just add water

*lose an HCl, left with an OH, HCl comes out as fumes and is thus called hydrogen chloride not hydrochloric acid*

Front 20

Haloalkane > Amine

Back 20

Heat in a sealed tube with conc NH3(alc)

*nucleophilic substitution, loses an HCl too*

Front 21

Acid chloride > Secondary amide

Back 21

Add amine

*would add ammonia for 1° but the R of an amine makes this 2°, need heat for polymer or else an acid base reaction occurs*

Front 22

Acid chloride > Ester

Back 22

Alcohol

*lose an HCl*

Front 23

Alcohol > Alkene

Back 23

Conc H2SO4 & heat

*dehydration via Saytzeff, thus 3° easier than 2° easier than 1°*

Front 24

Amine > Salt

Back 24

HCl

*classic acid base*

Front 25

Carboxylic acid > Amide

Back 25

Treat with (NH4)2CO3 then heat

Front 26

Amide > Carboxylic acid

Back 26

Heat with H+/H2O

*acid hydrolysis makes a carbo with NH4+ and base makes a coo- with ammonia*

Front 27

Carboxylic acid > COO-Na+

Back 27

Add NaOH

*base neutralizes carbo, Na makes the salt*

Front 28

Carboxylic acid > Amine+ & CHCOO-

Back 28

Mix with amine

*base neutralizes carbo giving us H for our amine+*

Front 29

Ketone > Secondary alcohol

Back 29

NaBH4 in alkaline conditions

Front 30

Aldehyde > Primary alcohol

Back 30

NaBH4 in alkaline conditions

Front 31

Triglyceride > Na salts of fatty acids

Back 31

Heat with NaOH(aq)

*this is saponification ie the making of salts, triglycerides are esters, and so the NaOH takes the wicket to COO-Na+ via alkaline hydrolysis*

Front 32

Tollens reagent?

Back 32

Aldehyde? Silver mirror when warmed and turns to carboxylic acid

Ketone? none

*Ag+/NH3*

Front 33

Benedict's solution?

Back 33

Aldehyde? Brick red Cu2O precipitate and changes to carboxylic acid when warmed

Ketone? None

*Cu2+ complex*

Front 34

Lucas reagent?

Back 34

3° alcohol? Rapid cloudiness

2°? Cloudy in 10 minutes

1°? None

*ZnCl2 / Conc HCl*

Front 35

Alkene > diol

Back 35

Acidified oxidant

*two OH groups join on the carbons that were double bonded*