Collin Jeremiah R. Balayan 2013 - 14713Experiment 8 Answers to Questions

1. Write the equations for all the tests giving positive results. Classify whether each of the reactions is a substitution or an addition reaction.

t-BuCl + AlCl3 -> t-Bu+ + AlCl4- ---- benzene ---> Addition

Limonene + Br2 (in light) -> Substitution

Benzene + Br2 -> HBr + Addition3C10H16 + 4KMnO4 + 8H2O -> 3C10H24O4 + 4MnO2 + 4KOH2 Hexane + O2 -> 12CO2 + 14H2O2 Limonene + O2 -> 20 CO2 + 6H2O2 Benzene + O2 -> 12 CO2 + 6 H2O2. What are the advantages of using steam distillation in extracting limonene?

Steam distillation is used to extract compounds like limonene that are temperature sensitive. Natural aromatic compounds like limonene dissolve in high temperatures. The steam carries vaporized limonene that is then condensed and separated with water because they are immiscible. This allows limonene to be extracted at lower temperature compared to other distillation techniques so that it will not dissolve.

Source: Organic Chemistry by Solomons

Collin Jeremiah R. Balayan 2013 - 14713Experiment 9 Answers to Questions

1. Arrange the compounds used in the experiment in order of increasing reactivity towards Br2 in CH3COOH. Explain

chlorobenzene -> benzene-> nitrophenol -> acetinilide -> phenol -> aniline

These compounds are arranged based on the properties of the groups connected to the benzene ring. The trend is that the stronger the electron donating group, the more reactive the compound and the stronger the electron withdrawing group, the less reactive the compound.

2. Do your experimental results agree with the theoretical data? If not, what are the possible sources of error?

The results did not match the theoretical data. Sources of error can include false positives, lack of definitive endpoint and wrong start of timing the reactions.

3. Predict the order of reactivity of the following compounds towards chlorination from the least reactive to the most reactive:A. Toluene, nitrobenzene, anisole and methylbenzoatenitrobenzene -> methylbenzoate -> toluene -> anisoleB. benzene, acetophenone, bromobenzene and benzyl alcoholacetophenone -> bromobenzene -> benzene -> benzyl alcoholC. styrene, benzaldehyde, aniline and iodobenzenebenzaldehyde -> Iodobenzene -> styrene -> aniline

4. Explain the effect of solvent in the reaction of acetanilide and Br2 in part B.

A more polar solvent can induce a stronger dipole in the Br2 molecule to make it more electrophilic so that it takes smaller activation energy for the reaction to occur.

Source: Organic Chemistry by Solomons