Medicines by Design - Organic reactions

18 important questions on Medicines by Design - Organic reactions

What conditions are needed to convert a primary alcohol into an alkene? What type of reaction is this?

Aluminium oxide (Al2O3 (s)) 300 degrees text-decorationOR conc sulphuric acid and reflux

= dehydration (elimination) reaction

What conditions are needed to convert a primary alcohol into an aldehyde? What type of reaction is this? What is the backwards reaction?

Alcohol to aldehyde = acidified potassium dichromate (Cr207 ^-2/H^+(aq))
                                          = distillation
                                          = oxidation

Aldehyde to alcohol = NaBH4
                                          = reduction

What conditions are needed to convert an aldehyde into a carboxylic acid? What type of reaction is this?

Acidified potassium dichromate, reflux = oxidation OR heat with Fehling's solution
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What conditions are needed to convert a carboxylic acid into an ester? What is the backwards reaction? What type of reactions are these?

Carboxylic acid to an ester = alcohol + conc sulphuric acid + reflux
                                                       = esterfication/ condensation

Ester to carboxylic acid = H+ (aq) or OH- (aq) + reflux
                                                 = hydrolysis 

What conditions are needed to convert an acyl chloride into an ester? What type of reaction is this?

Alcohol/ phenol
= acylation

What conditions are needed to convert a carboxylic acid into an acyl chloride?

SCl2O + reflux  + anhydrous conditions

What conditions are needed to convert an acyl chloride into a primary amide? What type of reaction is this?

Conc NH3 (aq) + room temperature
= acylation

What conditions are needed to convert a primary alcohol into an halogenoalkane? What type of reaction is this?

HBr (aq) + reflux

= Nucleophilic substitution 

What conditions are needed to convert an alkene into a halogenoalkane? What type of reaction is this?

Conc HBr (aq) at room temperature
= electrophilic addition

What conditions are needed to convert an alkene into an alkane? What type of reaction is this?

H2 (g) + finely divided Ni at 150 degrees & 5 atm OR Pt at room temperature & 1 atm
= Electrophilic addition

What conditions are needed to convert a halogenoalkane into an amine? What type of reaction is this?

Conc NH3 (aq) + heat in a sealed tube
= Nucleophilic substitution

What conditions are needed to convert a halogenoalkane into a nitrile? What type of reaction is this?

Sodium cyanide in ethanol + water + reflux
= Nucleophilic substitution

What conditions are needed for the bromination of benzene? What type of reaction is this?

FeBr3 OR Fe + Br2 (l) at room temperature
= electrophilic substitution

What conditions are needed for the chlorination of benzene? What type of reaction is this?

AlCl3 + Cl2 (g) at room temp
= electrophilic substitution

What conditions are needed for the alkylation of benzene to a carboxylic acid? What type of reaction is this?

AlCl3 + reflux + R-COCl / (RCO)2O anhydrous
= electrophilic substitution
= Friedal- Crafts reactions

What conditions are needed for the nitration of benzene? What type of reaction is this?

Conc HNO3 / conc H2SO4 + < 55 degrees
= electrophilic substitution

What conditions are needed for the reduction of nitrate benzene? What type of reaction is this?

Sn + conc HCl
= electrophilic substitution

Suggest a raw material from which prop-1-ene is produced in industry.

Crude oil

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