Diagram of OCR A-Level Chemistry A Organic Synthesis, 28.3: Synthetic Routes | Quizlet

Alkene + hydrogen /nickel catalyst/423K=

alkane

Alkene + bromine /room temperature=

dihaloalkane

Alkene + HCl(g/aq) /room temperature=

haloalkane (mixed products)

Alkene + H2O(g) /H3PO4=

alcohol (mixed products)

Primary alcohol + 2[O] /excess K2Cr2O7/H2SO4/reflux=

carboxylic acid

Primary alcohol + [O] /K2Cr2O7/H2SO4/distil=

aldehyde

Secondary alcohol + [O] /K2Cr2O7/H2SO4/reflux=

ketone

Alcohol + H3PO4 or H2SO4/reflux=

alkene + H2O

Alcohol + HBr /H2SO4/reflux=

haloalkane + H2O

Haloalkane + NaOH(aq)=

alcohol + sodium halide

Haloalkane + H2O=

alcohol + halide acid

Haloalkane + NH3=

primary amine + halide ion

Benzene + HNO3 /Conc. H2SO4/50C=

nitrobenzene + H2O

Benzene + 2HNO3 /Conc. H2SO4/70C=

dinitrobenzene + 2H2O

Benzene + Br2 /FeBr3 or AlBr3/room temperature & pressure

bromobenzene + HBr

Benzene + Cl2 /FeCl3 or AlCl3/room temperature & pressure

chlorobenzene + HCl

Benzene + haloalkane /AlCl3=

ethylbenzene + Hcl

Benzene + acyl chloride /AlCl3=

aromatic ketone + Hcl

Phenol + NaOH=

sodium phenoxide + H2O

Phenol + 3Br2 /room temperature=

2,4,6-tribromophenol + 3HBr

Phenol + dilute HNO3 /room temperature

2-nitrophenol or 4-nitrophenol

Aldehyde + [O] /K2Cr207/H2SO4/reflux=

carboxylic acid

Aldehyde + 2[H] /NaBH4/H20=

primary alcohol

Ketone + 2[H] /NaBH4/H2O=

secondary alcohol

Aldehyde + HCN(H2SO4/NaCN)=

hydroxynitrile

Carboxylic acid + metal=

carboxylate salt + H2

2Carboxylic acid + metal oxide=

carboxylate salt + H2O

Carboxylic acid + alkali=

carboxylate salt + H2O

2Carboxylic acid + carbonate=

carboxylate salt + H2O + CO2

Carboxylic acid + alcohol /Conc. H2SO4=

ester + H2O

Ester + H2O /dilute aqueous acid/reflux=

carboxylic acid + alcohol

Ester + OH-(aq) /reflux=

carboxylate ion + alcohol

Ester + SOCl2=

acyl chloride + SO2(g) + Hcl(g)

Acyl chloride + alcohol=

ester + HCl

Acyl chloride + phenol=

phenyl ester + HCl

Acyl chloride + 2NH3=

primary amide + ammonium chloride

Acyl chloride + 2amine

secondary amide + methyl ammonium chloride

Acid anhydride + H2O=

2carboxylic acid

Acid anhydride + alcohol=

carboxylic acid + ester

Acid anhydride + phenol=

carboxylic acid + ester

Acid anhydride + NH3=

primary amide + carboxylic acid

Acid anhydride + amine=

secondary amide + carboxylic acid

Amine + acid=

ammonium salt

1) Haloalkane + excess NH3=

2) Ammonium salt + NaOH=

1) ammonium salt

2) primary amine + sodium chloride + H2O

1) Haloalkane + primary amine=

2) Diammonium salt + NaOH=

1) diammonium salt

2) secondary amine

1) Haloalkane + secondary amine=

2) Triammonium salt + NaOH=

1) triammonium salt

2) tertiary amine

1) Nitrobenzene + 6[H] /tin/conc. HCl=

2) Phenylammonium chloride + excess NaOH=

1) phenylammonium chloride

2) phenylamine + water

Amino acid + HCl=

salt(NH3+) + Cl-

Amino acid + NaOH=

salt(COO-Na+) + H2O

Amino acid + alcohol /Conc. H2SO4=

ester

Amino acid at isoelectric point=

zwitterion (COO- and NH3+)

diester + diester=

polyester + H2O

Dicarboxylic acid + diol=

polyester + H2O

diamino acid + diamino acid=

polyamide + H2O

Diamine + diacyl chloride=

polyamide + HCl

Polyester + H+ /H2O=

dicarboxylic acid + diol

Polyester + NaOH /H2O=

diol + dicarboxylate(COO-Na+) salt

Polyamide + H+ /H2O=

dicarboxylic acid + diammonium(NH3+) salt

Polyamide + NaOH /H2O=

diamine + dicarboxylate(COO-Na+) salt

how do alkanes produce CO2 + H2O

- complete combustion

- via excess O2

how do alkanes produce CO, C + H2O

- incomplete combustion

- limited O2

how do we get from an alkane to a haloalkane

- via mechanism called

- free radical substitution:

- step 1:

=== turning halogen into halogen free radical

=== via in the presence of UV light

- step 2:

=== propagation step

- step 3:

=== termination step

how do we get from an alkene to an alkane and name the mechanism

- Hydrogen

- Ni Catalyst

- 150°C temp

- electrophilic addition

how do we get from an alkene to a dihalogenoalkane and name the mechanism

- halogen

- Cl2, Br2, I2 for example

- at room temperature

- Electrophilic addition

show and name the mechanism for alkene to dihaloalkane

how do we get from an alkene to a halogenoalkane and name the mechanism

- hydrogen halide

- at room temperature

- Electrophilic addition

show and name the mechanism for alkene to haloalkane

Electrophilic addition

name two ways to get from an alkene to an alcohol

- directly

- indirectly using H2SO4

how do we get from an alkene to an alcohol directly and name the mechanism

- hydration reaction

- Electrophilic addition

- 300°C

- 70 atm

- H3PO4 acid

- which acts as a catalyst

- by providing the H+ ion

show and name the mechanism for alkene to alcohol directly

Electrophilic addition

how do we get from an alkene to an alcohol indirectly using H2SO4 and name the mechanism

IN 2 STEPS:

step 1:

=== concentrated H2SO4

=== room temp

=== producing alkyl hydrogen sulphate

=== Electrophilic addition

step 2:

=== alkyl hydrogen sulphate to alcohol

=== hydrolysis via warm water

show and name the mechanism for first step in making alcohol from alkene indirecty, where alkene is converted to alkyl hydrogen sulphate

Electrophilic addition

how do we make a large number of smaller alkenes to 1 large alkene and name the mechanism

- radial initiator

- addition polymerisation

how do we get from a haloalkane to an alkene and name the mechanism

- KOH (ethanolic) reagent

- heat under reflux

- elimination

show and name the mechanism for a haloalkane to an alkene and name the mechanism

how do we get from a haloalkane to an alcohol and name the mechanism

- KOH (ethanolic) reagent

- heat under reflux

- nucleophilic substitution

show and name the mechanism for a haloalkane to an alcohol and name the mechanism

nucleophilic substitution

how do we get from a haloalkane to an nitrile and name the mechanism

- KCN dissolved in ethanol

- heat under reflux

- nucleophilic substitution

show and name the mechanism for a haloalkane to an nitrile and name the mechanism

nucleophilic substitution

how do we get from a haloalkane to an 1° Amine and name the mechanism

- NH3 ethanolic

- heat in a sealed tube

- under pressure

- nucleophilic substitution

show and name the mechanism for a haloalkane to an 1° Amine and name the mechanism

nucleophilic substitution

how do we get from a 1° alcohol to an aldehyde and name the type of reaction

- acidified K2Cr2O7

- distill out aldehyde

- as it forms

- using simple distillation apparatus

- oxidation

how do we get from a 1° alcohol to a Carboxylic acid and name the type of reaction

- excess acidified K2Cr2O7

- heat under reflux

- oxidation

how do we get from a 2° alcohol to a ketone and name the type of reaction

- excess acidified K2Cr2O7

- heat under reflux

- oxidation

how do we get from an alcohol to an alkene and name the mechanism

- conc H2SO4/ conc H3PO4

- dehydration

- elimination

show and name the mechanism for a alcohol to an alkene and name the mechanism

elimination

how do we get from an aldehyde to a 1° alcohol and name the type of reactions

- Method 1: Reduction

=== the addition of LiAlH or NaBH

=== at room temp and pressure

=== with a weak acid

=== which will supply the H+ ion.

- Method 2: Catalytic hydrogenation

=== where H+ and a Nickel catalyst

=== are added at HIGH PRESSURE

show and name the reduction mechanism for an aldehyde to a 1° alcohol

nucleophilic addition

how do we get from an aldehyde to a hydroxynitrile and name the mechanism

- KCN

- HCl aqueous

- nucleophilic addition

show and name the reduction mechanism for an aldehyde to a hydroxynitrile

nucleophilic addition

how do we get from a ketone to a 2° alcohol and name the type of reaction

- Method 1: Reduction

=== the addition of LiAlH or NaBH

=== at room temp and pressure

=== with a weak acid

=== which will supply the H+ ion.

=== nucleophilic addition

- Method 2: Catalytic hydrogenation

=== where H+ and a Nickel catalyst

=== are added at HIGH PRESSURE

show and name the reduction mechanism for a ketone to a 2° alcohol and name the mechanism

nucleophilic addition

how do we get from an ketone to a hydroxynitrile and name the mechanism

- KCN

- HCl aqueous

- nucleophilic addition

show and name the reduction mechanism for an ketone to a hydroxynitrile

nucleophilic addition

how do we get from a nitrile to a COOH and name the type of reaction

- dilute HCl (aq)

- Acid Hydrolysis

how do we get from a nitrile to a sodium carboxylate salt and name the type of reaction

- dilute NaOH (aq)

- Alkaline Hydrolysis

how do we get from a nitrile to an amine and name the type of reaction

- Hydrogen

- Ni Catalyst

- Reduction

how do we get from an COOH to an ester and name the mechanism

- add any OH

- add conc H2SO4

- which acts as a catalyst

- nucleophilic addition-elimination reaction

show and name the reduction mechanism for an COOH to an ester

nucleophilic addition-elimination reaction

how do we get from a 1° amine to 2° amide and name the mechanism

- Acyl chloride/ Acid anhydride

- room temp

- Nu add/elim