Summary of Organic Reactions - Weebly
Review: Organic Reactions (Answers)
Substitution Reactions
• Substitution of an alkane
|butane |+ |Br2 |[pic] |2-bromobutane + 1-bromobutane |+ |HBr |
• Substitution of benzene
|benzene |+ |Cl2(limited) |[pic] |chlorobenzene |+ |HCl |
| | | | | | | |
|chlorobenzene |+ |Cl2(limited) |[pic] |1,3-dichlorobenzne (major) |+ |HCl |
| | | | |+ 1,2-dichlorobenzne (minor) | | |
| | | | |+ 1,4-dichlorobenzne (minor) | | |
| | | | | | | |
|benzene |+ |bromopropane |[pic] |propylbenzene |+ |HBr |
• Substitution of an alkyl halide to form an amine
|2-bromopropane |+ |ammonia |[pic] |Propan-2-amine |+ |HBr |
| | | | | | | |
|iodoethane |+ |propanamine |[pic] |N-ethylpropanamine |+ |HI |
• Substitution of an alcohol with a hydrogen halide
|butan-2-ol |+ |HBr |[pic] |2-bromobutane |+ |H2O |
Addition Reactions
• Halogenation
|but-1-ene |+ |Br2 |[pic] |1,2-dibromobutane |
• Hydrogenation
|but-1-ene |+ |H2 |[pic] |butane |
• Hydrohalogenation
|but-1-ene |+ |HCl |[pic] |2-chlorobutane + 1-chlorobutane |
| | | | |(major) (minor) |
• Hydration
|but-1-ene |+ |H2O |[pic] |butan-2-ol + butan-1-ol |
| | | | |(major) (minor) |
• Addition to Alkynes
|but-1-yne |+ |Br2 |[pic] |1,2-dibromobut-1-ene |
| | |(limited) | | |
| | | | | |
|but-1-yne |+ |Br2 |[pic] |1,1,2,2-tetrabromobut-1-ene |
| | |(excess) | | |
| | | | | |
Elimination Reactions
• Elimination of Alkyl Halides
2-bromopentane + NaOCH2CH3 → pent-2-ene or pent-1-ene + ethanol + NaBr
• Elimination of Water
|2-pentanol |[pic] |2-pentene + 1-pentene |+ |H2O | |
Oxidation Reactions
propan-1-ol + KMnO4 [pic] propanal
propan-2-ol + H2O2 [pic] propanone
propanal + K2Cr2O7 [pic] propanoic acid
Reduction Reactions
|butanal |+ |H2 |[pic] |butan-1-ol |
|but2-ene |+ |H2 |[pic] |butane |
Condensation Reactions
|Condensation of two alcohols |
|methanol |+ |propan-2-ol |[pic] |2-methoxypropane |+ |H2O |
| |
|Condensation of an alcohol and a carboxylic acid |
|ethanol |+ |butanoic acid |[pic] |ethyl butanoate |+ |H2O |
| |
|Condensation of an alcohol and a carboxylic acid |
|propan-1-amine |+ |ethanoic acid |[pic] |N-propylethanamide |+ |H2O |
|N-ethyl propanamine |+ |butanoic acid |[pic] |N-ethyl-N-propylbutanamide |+ |H2O |
Hydrolysis Reactions
|Hydrolysis of esters |
|propyl butanoate |+ |H2O |[pic] |propan-1-ol |+ |butanoic acid |
|propyl ethanoate |+ |H2O |[pic] |propan-1-ol |+ |ethanoic acid |
| |
|Hydrolysis of amides |
|N-ethyl butanamide |+ |H2O |[pic] |ethanamine |+ |butanoic acid |
|N-ethyl-N-butyl propanamide |+ |H2O |[pic] |N-ethylbutanamine |+ |propanoic acid |
Practice – Organic Reactions
1. Identify the following reactions as a substitution, addition, elimination, reduction, oxidation, condensation or hydrolysis reaction.
|a. |substitution |penta|+ |chlorine |[pic] |2-chlor|+ |
| | |ne | | | |opentan| |
| | | | | | |e | |
|c. |butan-2-ol |+ |HBr |[pic] |2-bromobutane |
i. |2-bromopropane |+ |NaOCH2CH3 |[pic] |propene |+ |NaBr + ethanol |
| |j. |propan-2-ol | | |[pic] |propene |+ |H2O | | |
2. For each reaction, give the reactants and catalysts that are needed to produce the given product.
a. |propene |+ |HCl |[pic] |2-chloropropane | |
| |b. |ethene |+ |Br2 |[pic] |1,2-dibromoethane | | | |c. |3-methylpent-2-ene |+ |H2O |[pic] |3-methylpentan-3-ol | | | |d. |benzene |+ |Cl2 (limited) |[pic] |chlorobenzene | | | |e. |ethanol |+ |ethanol |[pic] |ethoxyethane |+ |H2O | |f. |chloroethane |+ |benzene |[pic] |ethylbenzene |+ |HCl | |g. |propanoic acid |+ |pentanol |[pic] |pentyl propanoate | | | |h. |2-chlorobut-1-ene |+ |HCl |[pic] |2,2,-dichlorobutane |
| | |i |N-methylethanamine |+ |butanoic acid |[pic] |N-ethyl-N-methylbutanamide |+ H2O | |
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