Chemistry Reactions Flashcards by Susannah Rennoldson

Acyl chloride + Alcohol

RCOCl + HOR’ —> RCOOR’ + HCl
Acylation, esterification
Room temperature

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Ester —> Alcohol and Carboxylic Acid

RCOOR’ —> RCOOH + HOR’
Heat under reflux with water and H+ ions (reversible reaction)
Hydrolysis reaction

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Alcohol + Carboxylic Acid —> Ester

RCOOH + R’OH —> RCOOR’ + H20
Esterification, condensation reaction
Heat under reflux with c.H2SO4 or HCl

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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`

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Alkane —> Haloalkane

RCH3 + Br2 —> RCH2Br + HBr
Radical chain reaction
Need Br2 and sunlight
(Normal initiation, propogation, termination reaction)

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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

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Haloalkane + OH- —> Primary alcohol

RCH2Br + NaOH —> RCH2OH + NaBr
Heat under reflux with NaOH (for hydroxide ions)
Nucleophillic substitution

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Haloalkane + H2O —> Primary alcohol

RX + H2O —> ROH + H+ + X-
Heat under reflux with water. Slower than reaction with OH-
Nucleophillic substitution

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Primary alcohol —> Haloalkane

RCH2OH + X- + H+ —> RCH2X + H20
Heat under reflux with NaBr (Br- ions) and c. Sulfuric acid
Nucleophillic substitution

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Nitrobenzene —> Phenylamine

Benz-NO2 —> Benz–NH2

Data sheet
Reduction
Heat under reflux with SN and c.HCl

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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

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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

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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

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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

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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

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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

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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)