Compound Alkene (C=C)

Reactions undergone Nucleophilic addition

With what compound? H2, (Ni catalyst, 150C or Pt catalyst) Catalytic hydrogenation HX (RT), X is halogen Electrophilic addition Concentrated H2SO4, water

What is formed Alkane Halogenoalkane Alcohol

Remarks

Position depends on stability and where the C=C double bond was (Markovnikovs rule)

Oxidation with KMnO4

Alkane Halogenoalkane (R-X)

Free radical substitution Nucleophilic substitution

CHR end of alkene CRR end of alkene CH2 end of terminal alkene X2, X is halogen NaOH, Reflux NaCN, ethanolic, heat Excess ammonia Concentrated NaOH in ethanol, reflux Cr2O72- or KMnO4, acidified

Aldehyde Ketone CO2, H2O Halogenoalkane Alcohol Nitrile Amine Alkene Aldehyde

Effervescence observed in QA Markovnikovs rule applies (stability and position) OH group replaces halogen CN group replaces halogen. One extra Carbon.

Elimination Alcohol (OH) Oxidation

Nucleophilic substitution Dehydration Iodoform test

PBr3, concentrated H2SO4, refluxed H2SO4, heat Iodine and sodium hydroxide

Ketone Halogenoalkane Alkene Carboxylate ion

Primary alcohol becomes this *To get an aldehyde, use K2Cr2O7 acidified, heat w/ immediate distillation Secondary alcohol becomes this

2 products, look at OH group Pale yellow precipitate of CHI3 formed.

Aldehyde

Oxidation

Tollens Reagent, warm Fehlings Solution, warm I2 (aq), NaOH, warm K2Cr2O7 or KMnO4 oxidized HCN, KOH HCN, KCN KCN, H2SO4 2, 4-DNPH LiAlH4, dry ether I2 (aq), NaOH, warm HCN, KOH HCN, KCN KCN, H2SO4 2, 4-DNPH Alcohol, R-OH, with concentrated H2SO4, heat PCl5 or SOCl2 LiAlH4, dry ether Dilute HCl LiAlH4, dry ether Water Alcohol

Carboxylate ion Carboxylate ion Carboxylate ion Carboxylic acid Nitrile with alcohol group *Cyanohydrin Orange precipitate Primary alcohol Carboxylate ion Nitrile with alcohol group *Cyanohydrin Orange precipitate Ester Acyl chloride Alcohol Carboxylic acid Amine Carboxylic acid Ester

Nucleophilic addition

Silver mirror formed Red PPT of Cu2O formed Yellow PPT of CHI3 formed From primary alcohol, can go straight to this One extra carbon than before

Condensation Reduction Oxidation Nucleophilic addition

C=O bond cutaway

Ketone

Yellow PPT of CHI3 formed. This only happens with methyl ketones One extra carbon than before (step up reaction) C=O bond cutaway H2SO4 acts as a catalyst White fumes observed as well Ammonium chloride produced as a side product HCl byproduct

Condensation Carboxylic acid Fission of C-O bond

Nitrile

Reduction Acidic hydrolysis Reduction Hydrolysis Nucleophilic

Acyl chloride

substitution Benzene
*remark: ALL benzene reactions apply for methylbenzene as well. *remark: the CH3 on methylbenzene behaves like a typical alkane.

Electrophilic substitution

Phenol Amine, ammonia Concentrated HNO3 Concentrated H2SO4 30C Cl2, AlCl3

Ester Amide

Alkaline medium PREFERRED 2,4 directing for methylbenzene

2,4 directing for methylbenzene

Br2, FeBr3

2,4 directing for methylbenzene

RCl, AlCl3 (Friedel-Crafts Alkylation)

2,4 directing for methylbenzene Diagram is inaccurate

Methylbenzene Specific Phenol

Addition Oxidation

Acyl chloride, AlCl3 H2, Ni Cr2O72- or KMnO4, acidified

Ester Cyclohexane Benzoic acid

2,4 directing for methylbenzene EVERY SINGLE BENZENE RING WITH ANY ALKYL GROUP ATTACHED DOES THIS. White fumes of HCl evolved 2,4 directing, applies to Cl2 as well 2 next to, 1 opposite 2,4 directing 2 next to, 1 opposite

Acylation Electrophilic substitution

Acyl chloride Br2 in CCl4, room temperature Br2 (aq) Dilute HNO3, room temperature Concentrated HNO3, room temperature

Ester Phenol with 1 Br Phenol with 3 Br Phenol with 1 NO2 Phenol with 3 NO2

Distinguishing tests to confirm whats what - 2,4 DNPH: Used to confirm presence of aldehydes or ketones - Sodium Carbonate: Only carboxylic acids react with it - Iodoform test: Used to confirm presence of CH3CO group, as with a methyl-aldehyde, methyl ketone or methyl alcohol. - Aqueous Bromine: Decolorizes when alkenes and phenols are present - Bromine in CCl4: Decolorizes N-phenyl-ethanamides, (phenylamines,) phenols and alkenes. - Tollens Reagent: Oxidizes aldehydes and benzaldehydes to form a silver mirror (Ag) - Fehlings Reagent: Oxidizes aldehydes to form a reddish brown precipitate of copper (I) oxide. o Cant oxidize benzaldehydes because alkaline condition causes benzaldehyde to disproportionate. - Neutral iron (III) chloride: reacts with phenols to form a violet coloration