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III. RESULTS AND DISCUSSION A. Investigation of Hydrocarbons 1.

Solubility behavior Sample Cyclohexane (clear liquid) Benzene (clear liquid) Toluene (clear liquid) Solvent H2 0 clear, immiscible, with emulsions clear, immiscible, no emulsions clear, immiscible, no emulsions CCl4 clear, miscible, no emulsions clear, miscible, no emulsions clear, miscible, no emulsions NaOH clear, immiscible, with emulsions clear, immiscible, slight emulsions clear, immiscible, with emulsions H2SO4 clear, immiscible, with emulsions white, immiscible, with emulsions immiscible- upper layer: clear; loweryellow

2. Halogenation: Reaction with Bromine Sample Cyclohexane Test tube not covered with carbon paper clear, light orange solution pale yellow solution without precipitate yellow-orange solution Test tube covered with carbon paper clear, very light orange solution Clear yellow liquid with white precipitate clear, light yellow solution

Benzene

Toluene

3. Oxidation: Reaction with Baeyer’s Reagent Sample Cyclohexane Benzene Toluene Color Changes Negative Negative Negative

4. In order to determine if a substance is more acidic than others. Preparation and Testing of Acetylene Gas CaC2 + 2H20 C2H2 + Ca(OH)2 Tests H2O CCl4 Solubility behavior NaOH H2SO4 Covered with carbon paper Halogenation Uncovered with carbon paper Oxidation Reaction with ammoniacal silver nitrate Acetylene Gas clear clear clear clear brownish orange solution 2 distinct layers. upper: clear solution Positive Cloudy solution with white precipitate Carbon tetrachloride (CCl4) is an inert solvent and is unable to react with either bromine or the samples. Terminal alkynes are acidic because of the stability of their conjugate base. Reaction with ammoniacal silver nitrate Sample Cyclohexane 2 clear distinct layers B. CCl4 basically gives space for the reaction to take place.lower: light yellow. we must always compare the stability of their conjugate bases. Based on the reaction below. when a base reacts with an acid. because a solvent must not participate and must be inert to the type of reaction. This makes it a good solvent in which the bromination reaction took place. the hydrogen is .

This gives benzene a positive charge. The nature of the hybrid orbital containing the electron pair is important. This gives bromine a positive charge. restabilizing the catalyst FeBr3. + H Br2 FeBr3 Br + HBr The mechanism involved in the bromination of benzene is the same for toluene. there are 3 isomers formed in different ratios. The hydrogen bonds with bromine forming HBr. forming an anion. when benzene is introduced to it. Increased s character (sp= 50%. FeBr3 acts as a Lewis acid and removes an electron from Br 2. it immediately removes an electron from the double bond of benzene and bonds to it. However. The hydrogen in benzene is then removed and the electron is used to restore the double bond. sp2 = 33% and sp3 = 25%) implies that the alkyne sp orbital is closer to the nucleus and so there is greater electrostatic stabilization of the electron pair. Therefore the conjugate base of the alkyne is the most stable and the most readily formed.removed from it. Since it is highly electronegative. . The bromination of benzene (C6H6) occurs with the presence of iron (III) bromide (FeBr3).

the bromine molecule is broken. There are three steps involved: initiation. Alkylation is the introduction of an alkyl group to benzene ring. propagation and termination. the termination involves reactions which remove free radicals from the system without replacing them by new ones. The propagation involves reactions that keep the chain of free-radical going. in the presence of AlCl3 to generate a . Lastly.CH3 CH3 Br CH3 CH3 + Br2 FeBr3 + Br Br HBr The bromination of cyclohexane is a free-radical substitution and does not take place without the presence of light. The reaction is carried out by treating the benzene with ethyl chloride. In initiation.

Aluminum chloride catalyzes the reaction by helping the ethyl chloride to dissociate in much the same way that FeBr 3 catalyzes aromatic brominations by helping Br2 dissociate. Loss of H+ then completes the reaction The following reactions with their respective reaction conditions differentiate the reactants from their products: 1-butyne KOH 200oC 2-butyne 2-methylpentane NBS. 10 atm 2-methyl-2-pentene . ROOR 2-methyl-2-pentene toluene H2. raney nickel 450 K.carbocation electrophile. CCl4 light.