Organic Reactions A2 - CIE A Level Chemistry 9701

Comprehensive vocabulary flashcards covering organic reaction pathways, conditions, and mechanisms for CIE A Level Chemistry (9701) A2 level.

Benzene to cyclohexane

Requires $H_2$, $Pt/Ni$ catalyst, and heat; occurs via electrophilic addition.

Benzene to chlorobenzene

Requires $Cl_2$ bubbled in and UV light; occurs via electrophilic addition.

Benzene to bromobenzene

Requires anhydrous dry $AlBr_3$ catalyst (forms $AlBr_4^- + Br^+$) and heat under reflux; occurs via electrophilic substitution and forms $2$ or $4$-bromobenzene, or $2,4,6$-tribromobenzene when benzene is in excess.

benzene to methylbenzene

Requires chloromethane and $AlCl_3$ catalyst with heat; known as friedel-crafts alkylation via electrophilic substitution.

benzene to aromatic ketone (phenylthanone)

Requires Acyl Chloride and an $AlCl_3$ Catalyst (Acylation) plus heat.

benzene to nitrobenzene

Requires conc $HNO_3$, conc $H_2SO_4$ catalyst, and heat under reflux at $55^\circ C$ with constant agitation; reaction steps include: $HN03 + H_2S04 \rightarrow H_2NO_3 + HSO_4^-$ and $H_2NO_3 + H_2SO_4 \rightarrow NO_2^+ + HS04^- + H_30^+$.

methylbenzene to benzenecarboxylic acid

Requires alkaline $KMnO_4$ fol lowed by $H_2SO_4$ and heat under reflux.

phenol to sodium phenoxide

Reaction with $Na$ (forms $H_2$) or $NaOH$ (forms $H_2O$) via an acid-base reaction.

phenol to bromophenol

Requires $Br_2(aq)$ at room temp; observations include bromine water decolourises and a white ppt forms.

phenol to nitrophenol

Requires + dilute $HNO_3$ at room temp.

phenol to ester

Requires + acyl chloride where phenol must be dissolved in $NaOH$; produces steamy misty $HCl$ fumes.

phenol to aromatic ester

Requires + aromatic acyl chloride where phenol must be dissolved in $NaOH$; produces steamy misty $HCl$ fumes.

methanoic acid oxidation

Requires Tol lens/ Fehling's reagent (produces silver mirror/ brick red ppt); produces $CO_2 + 2H^+ + e^-$; observation: $CO_2$ effervescence which turns limewater cloudy.

ethanedioic acid oxidation

Requires warm acidified $KMnO_4$ (note: doesn't work with Tol lens/ Fehling's); produces $2CO_2 + 2H^+ + 2e^-$.

carboxylic acid to acyl chloride (PCl5)

$RCOOH + PCl_5 \rightarrow RCOCl + POCl_3 + HCl$ at room temp.

carboxylic acid to acyl chloride (PCl3)

$3RCOOH + PCl_3 \rightarrow 3ROCl + H_3PO_3$ with heat.

carboxylic acid to acyl chloride (SOCl2)

$RCOOH + SOCl_2 \rightarrow RCOCL + SO_2 + HCl$ at room temp.

acyl chloride to carboxylic acid

Requires + $H_2O$ via nucleophilic addition-elimination (condensation); produces steamy misty $HCl$ fumes.

acyl chloride to amide

Requires + $2NH_3$ at room temp via nucleophilic additon-elimination.

acyl chloride to n-substituted amide

Requires + primary amine via nucleophilic addition-elimination; produces steamy misty $HCl$ fumes.

acyl chloride to ester

Requires + alcohol/ phenol in $NaOH$ at room temp; produces steamy misty $HCl$ fumes.

nitrobenzene to phenylamine

Requires tin and conc $HCl$ (produces phenylammonium chloride) fol lowed by $NaOH(aq)$ and heat under reflux.

phenylamine to phenylammonium ion

• $H_2O \rightarrow$ phenylammonium ion + hydroxide ion; + $HCl \rightarrow$ phenylammonium chloride; + dilute $H_2SO_4 \rightarrow$ phenylammonium + $HS04^-$.

phenylamine to bromophenylamine

Requires + $Br_2(aq)$ at room temp; produces a white ppt.

Phenylamine to Benzenediazonium Chloride

Requires + $HNO_2$ (nitrous acid) made in situ ($NaNO_2 + HCl \rightarrow NaCl + HNO_2$) at a temp of $0-10^\circ C$; if higher than $10^\circ C$, decomposes to phenol: $C_6H_5N_2Cl + H_2O \rightarrow C_6H_5OH + N_2 + HCl$.

benzenediazonium ion to hydroxyazobenzene

Requires + phenol cooled to $0-10^\circ C$ and dissolved in $NaOH$.

benzenediazonium ion to aminoazobenzene

Requires + phenylamine to form $4$-aminoazobenzene + $H^+$.

hydrolysis of amides by HCl

amide + $H_2O + HCl \rightarrow$ carboxylic acid + ammonium chloride with heat.

hydrolysis of amides by NaOH

$RCONH_2 + NaOH \rightarrow RCOO^-Na^+ + NH_3$ (heat); followed by $RCOO^-Na^+$ with $HCl/ H_2SO_4 \rightarrow RCOOH + NaCl/ Na_2SO_4$.

Amino Acids in Acidic Conditions

Amino acid is ful ly protonated i.e. ($-NH_3^+$) and ($-COOH$); overal l charge = $+1$.

amino acids in alkaline conditions

Presents as $COO^-$ and $NH_2$; overal l charge = $-1$.

amino acids at ph 7

Form zwitterions; present as $COO^-$ and $NH_3^+$.