Chemistry Reactions Flashcards
Acyl chloride + Alcohol
RCOCl + HOR’ —> RCOOR’ + HCl
Acylation, esterification
Room temperature
Ester —> Alcohol and Carboxylic Acid
RCOOR’ —> RCOOH + HOR’
Heat under reflux with water and H+ ions (reversible reaction)
Hydrolysis reaction
Alcohol + Carboxylic Acid —> Ester
RCOOH + R’OH —> RCOOR’ + H20
Esterification, condensation reaction
Heat under reflux with c.H2SO4 or HCl
Coupling Reaction
Diazonium to Azo
Benz-N2+ + Benz-X —> Benz-N2-Benz-X (azo) + H+
Make solution of coupling agent
-in NaOH if phenol
- X must be OH or NH2. Increase electron density and reactivity to electrophiles
Add Ice cold diazonium salt solution
Electrophillic Substitution`
Alkane —> Haloalkane
RCH3 + Br2 —> RCH2Br + HBr
Radical chain reaction
Need Br2 and sunlight
(Normal initiation, propogation, termination reaction)
Diazotisation
Aromatic amine to diazonium compound
Benz-NH2 + HNO2 + H+ —> Benz-N2+ + 2H20
Aromatic amine dissolved in dilute HCl. Cold sodium nitrate (III( solution added (NaNO2). HCl and NaNo2 form unstable nitrous acid which reacts with amine group
Need sodium nitrate(III) solution, dilute HCL, keep under 5 C
Haloalkane + OH- —> Primary alcohol
RCH2Br + NaOH —> RCH2OH + NaBr
Heat under reflux with NaOH (for hydroxide ions)
Nucleophillic substitution
Haloalkane + H2O —> Primary alcohol
RX + H2O —> ROH + H+ + X-
Heat under reflux with water. Slower than reaction with OH-
Nucleophillic substitution
Primary alcohol —> Haloalkane
RCH2OH + X- + H+ —> RCH2X + H20
Heat under reflux with NaBr (Br- ions) and c. Sulfuric acid
Nucleophillic substitution
Nitrobenzene —> Phenylamine
Benz-NO2 —> Benz–NH2
Data sheet
Reduction
Heat under reflux with SN and c.HCl
Benzene —> Nitrobenzene
nitration
Benz + HNO3 ---> Benz-NO2 + H2O Conc. HNO3 catalyst. Keep under 55 Electrophillic substitution 1) HNO3 + 2H2SO4 ---> NO2+ + 2HSO4- + H30+ - products are the nitrating mixture 2) Benz + NO2+ ---> Benz-NO2 + H+ 3) H+ + 2H2SO4- + H3O+ ---> 2H2SO4 + H20
Benzene- Sulfobenzene
sulfonation of benzene
Benz + c.H2SO4 ---> Benz-SO3H + H+ Heat under reflux with c. H2SO4. OR at 40 with fuming H2SO4 Electrophillic substitution 1) H2SO4 ---> H2O + SO3+ 2) Benz + SO3+ ---> Benz-HSO3+ Benz-HSO3 ---> Benz-SO3H
Benzene —> Chlorobenzene
chlorination
Benzene + Cl2 ---> Benz-Cl + HCl React at room temperature with anhydrous AlCl3 Electrophillic substitution 1. Cl2 + AlCl3 ---> Cl+ + AlCl4- 2. Benz + Cl+ ---> Benz-Cl + H+ 3. H+ + AlCl4- ---> HCl + AlCl3
Benzene —> Bromobenzene
(bromonation
Benzene + Br2 ---> Benz-Br + HBr Heat with Iron(III) bromide catalyst Electrophillic substitution 1. Br2 + FeBr3 ---> Br+ + FeBr4 2. Benzene + Br+ ---> Benz-Br + H+ 3. H+ + FeBr3- ---> HBr + FeBr3
Benzene —> Benzene-R
Friedel-Crafts alkylation
Benzene + RCl ---> Benz-R + HCl Heat under reflux with R and anhydrous AlCl3 Electrophillic substitution 1. RCl + AlCl3 ---> R+ + AlCl4- 2. Benzene + R+ ---> Benzene-R + H+ 3. H+ + AlCl4- ---> HCl + AlCl3
Benzene —>Benzene-OR
Friedel-Crafts Acylation
Benzene + RCOCl ---> Benz-OR + HCl React with acyl chloride with anhydrous AlCl3 catalyst. Or use an acid anhydride Electrophillic substitution 1. RCOCl + AlCl3 ---> RCO+ + AlCl4- 2. Benzene + RCO+ ---> Benz-C(O)R + H+ 3. H+ + AlCl4- ---> HCl + AlCl3
Haloalkane —> Amine
RX + NH3 —> RNH3+X- RNH2 + X- + H+
Nucleophillic substitution
Heat in a sealed tube with c. NH3 solution
Electrophillic substitution
Bromination, Chlorination, Friedel-Crafts, Nitration, Sulfonation
Need some kind of catalyst to make the electrophile
Keeps stable benzene system
Nucleophillic addition
Aldehyde/ketone + cyanohydrin reactions
CN acts as nucleophile
Electrophillic addition
CH2CH2 + X-X —> CH2XCH2X
Electrophile may be polarised by proximity to negative region
Electrons from negative region attack positive electrophile (whose electrons move to negative region)
Double bond breaks, making one carbon a carbocation and X ion
Electrons from X ion attacks carbocation to form covalent bond
Aldehyde/Ketone —> Cyanohydrin
(R-C-OH)
(R’/ \CN)
RC(O)R’ + CN- —> R(R’)C(OH)(CN)
React in solution, in acidic conditions with CN- ions
Nucleophillic addition
Nucleophile
Nucleophile- (molecule/ negative ion) with a lone pair of electrons that it can donate to a positively charged atom to form a covalent bond
Alkene —> Haloalkane
CH2H2 + HBr —> CH3CH2Br
React at room temperature with a solution of HBr
(Electrophillic addition)
OR a radical chain reaction with HBr(g)
Alkene —> Alkane
CH2CH2 + H2 —> CH3CH
150 c, 5atm, Finely powdered Nickel catalyst, H2 gas
Electrophillic addition
Alcohol —> Carboxylic Acid
ROH —> ROOH
Heat under reflux with excess chromate ions and H+
Oxidation
Aldehyde —> Carboxylic Acid
Heat under reflux with acidified potassium dichromate
Oxidation
Aldehyde —> Primary Alcohol
Reduction with NaBH4
Data sheet
Primary Alcohol —> Aldehyde
ROH —> RCHO
Heat under reflux with acidified potassium dichromate. Distil in situ. Excess alcohol
Oxidation
Secondary alcohol —> Ketone
R(H)OHR’ —> RC(O)R’
Heat under reflux with acidified potassium dichromate
Oxidation
Primary alcohol —> Alkene
ROH —> R + H20
Dehydration. Elimination.
300 C with Alumina catalyst (Al2O3)
or Heat under reflux with c. H2SO4
Alkene —> Primary alcohol
Alkene + H20 —> Alcohol
Electrophillic Addition
Industrial- High temp, high pressure, presence of catalyst (phophoric acid on silica)
Lab- React ethene with c. H2SO4 then dilute with water. Adds on OSO3H group, the lose SO3H to OH- ions and gain H+
Carboxylic Acid —> Acyl chloride
RCOOH +SOCl2 —> RCOCl + SO2 + HCl
Substitution reaction
Heat under reflux with SCl2O
Acyl chloride —> Secondary amide
RCOCl + RNH2 —> RC(O)NHR + HCl
Acylation reaction, Condensation
Room temperature, RNH2
Haloalkane —> Nitrile
R-X + CN- —> RCN + Br-
Data sheet
Acyl Chloride —> Primary amide
RCOCl + R’NH2 —> RCONHR’ + HCl
Acyl chloride + amine —> amide + HCl
Nitrile —> Carboxylic Acid
RCN —> RCOOH
Heat under reflux, H+ ions
Data sheet
Nitrile —> Amine
Nitrile + 2H2 —-> CHNH2
Palladium catalyst, high temp and pressure
(May not be necessary)
Nucleophillic substitution
Nucleophile attacks delta -ve C atom
Nucleophile donate two electrons to form dative covalent bond
C-X bond breaks heterolytically, producing negative ion
R-X + Nu- —> R-Nu + X-
Electrophile`
A positive ion/ partial positive molecule, that will be attracted to a negatively charged region and react by accepting a lone pair of electrons to form a covalent bond
Amide —> Carboxylic acid
acid hydrolysis
Amide + Acid —> Carboxylic acid + Amine salt
Amide
alkaline hydrolysis
1 Amide + alkali —> Carboxylate ion + ammonia (g)
2 Amide + alkali —> Carboxylate ion + amine
Need mod concentrated alkali (NaOH)
