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 | |

................
................

In order to avoid copyright disputes, this page is only a partial summary.

Google Online Preview   Download