0 penilaian0% menganggap dokumen ini bermanfaat (0 suara)
286 tayangan8 halaman
Hydrogenation adds hydrogen to alkenes in the presence of a metal catalyst to form alkanes. Dehydrogenation removes hydrogen from alkanes to form alkenes, such as by reacting an alkyl halide with alcoholic potassium hydroxide. Lucas' reagent uses zinc chloride and hydrochloric acid to differentiate primary, secondary, and tertiary alcohols based on their differing reaction rates. Tollen's reagent, Fehling's solution, and Schiff's reagent can test for aldehydes based on characteristic color changes.
Hydrogenation adds hydrogen to alkenes in the presence of a metal catalyst to form alkanes. Dehydrogenation removes hydrogen from alkanes to form alkenes, such as by reacting an alkyl halide with alcoholic potassium hydroxide. Lucas' reagent uses zinc chloride and hydrochloric acid to differentiate primary, secondary, and tertiary alcohols based on their differing reaction rates. Tollen's reagent, Fehling's solution, and Schiff's reagent can test for aldehydes based on characteristic color changes.
Hydrogenation adds hydrogen to alkenes in the presence of a metal catalyst to form alkanes. Dehydrogenation removes hydrogen from alkanes to form alkenes, such as by reacting an alkyl halide with alcoholic potassium hydroxide. Lucas' reagent uses zinc chloride and hydrochloric acid to differentiate primary, secondary, and tertiary alcohols based on their differing reaction rates. Tollen's reagent, Fehling's solution, and Schiff's reagent can test for aldehydes based on characteristic color changes.
Question 2 : Explain in details about hydrogenation of alkene and dehydrogenation of
alkane. Support your explanation with suitable chemical equations.
Hydrogenation is the reaction of the carbon-carbon double bond in alkenes with hydrogen in the presence of a metal catalyst. The application of this reaction is includes the manufacture of margarine from animal or vegetable fats and oils. One of the hydrogenation simplest cases is the hydrogenation of ethane. Ethene reacts with hydrogen in the presence of a finely divided metal catalyst such as nickel, platinum, palladium and rhodium at a temperature of about 150C.
This reaction is an example of a heterogeneous catalysis process which the reaction takes place on the surface of the metal. Ethene molecules are adsorbed on the surface of the metal catalyst, nickel. The double bond between the carbon atoms breaks and the electrons are used to bond it to the nickel surface.
Hydrogen molecules are also adsorbed on to the surface of the nickel. When this happens, the hydrogen molecules are broken into atoms. These can move around on the surface of the nickel.
If a hydrogen atom diffuses close to one of the bonded carbons, the bond between the carbon and the nickel is replaced by one between the carbon and hydrogen.
That end of the original ethene now breaks free of the surface, and eventually the same thing will happen at the other end.
As before, one of the hydrogen atoms forms a bond with the carbon, and that end also breaks free. There is now space on the surface of the nickel for new reactant molecules to go through the whole process again
Whereas, dehydrohalogenation is a reverse reaction of hydrogenation/halogenations/halo in order to obtain alkenes. For example, an organic reaction in which alkyl halide when boiled with alcoholic alkali gives corresponding alkene. It is also called a -Elimination reaction and is a type of elimination reaction. In this reaction, the halogen on the carbon in the alkyl halide reacts with hydrogen present on the -carbon releasing hydrogen halide. Hence an alkene is formed due to formation of a double bond between the - and -carbon.Zaitsev's rule helps to explain regioselectivity for this reaction type. The opposite transformation is called hydrohalogenation.
Reactions
Here ethyl chloride reacts with potassium hydroxide dissolved in ethanol, giving ethene. Likewise, 1-chloropropane and 2-chloropropane give propene. Chlorobenzene does not react with potassium hydroxide due to the presence of the benzene ring, which, due to stabilization as a result of aromaticity, does not give conventional elimination, as it would lead to a very unstable benzyne intermediate. In general, the above reaction of haloalkane with potassium hydroxide would compete with an Sn2 nucleophilic substitution reaction (minor product) because OH - is a strong, sterically unhindered nucleophile. Perhaps a better reagent would be a deprotonated alcohol such as potassium tert- butoxide ([CH 3 ] 3 CO - K + ) or, because it is an oxide anion and thus a strong base and nucleophile, potassium ethoxide (CH 3 CH 2 O - K + ), and because of steric hindrance, thereby promoting an elimination mechanism instead of a substitution mechanism.
Question 2 : What is Lucass reagent and how it can be used to differentiate primary, secondary and tertiary alcohol?
Lucas' reagent is a solution of anhydrous zinc chloride in concentrated hydrochloric acid. This solution is used to classify alcohols of for low molecular weight alcohols and it distinguishes the rates of reaction of alcohols. The reaction is a substitution in which the chloride replaces a hydroxyl group. Positive indicator of the reaction is the formation of a water insoluble alkyl chloride as cloudiness or a precipitate, signalling formation of a chloroalkane. The formation of an alkyl chloride with tertiary alcohol is very rapid, followed by the secondary alcohol that may take from 5 to 20 minutes to form visible cloudiness. Primary alcohols do not react with Lucas reagent or it may show very little result in a very long time. The chemical reaction involves replacing the OH group of the alcohol with a chloride ion from hydrochloric acid (HCl), forming an alkyl chloride, as shown in the following equation. ROH + HCl RCl + H 2 O
The differing reactivity reflects the differing ease of formation of the corresponding carbocations. Tertiary carbocations are far more stable than secondary carbocations, and primary carbocations are the least stable. An equimolar mixture of ZnCl 2 and HCl is the reagent. The mechanism start when the alcohol is protonated by this mixture, and H 2 O group attached to carbon is replaced by the nucleophile Cl - , which is present in excess. Tertiary alcohols react immediately with Lucas reagent as evidenced by turbidity owing to the low solubility of the organic chloride in the aqueous mixture. Secondary alcohols react within five or so minutes (depending on their solubility). Primary alcohols do not react appreciably with Lucas reagent at room temperature. Hence, the time taken for turbidity to appear is a measure of the reactivity of the class of alcohol, and this time difference is used to differentiate between the three classes of alcohols: no visible reaction at room temperature and cloudy only on heating: primary, such as normal amyl alcohol (1-Pentanol) solution turns cloudy in 35 minutes: secondary, such as sec-amyl alcohol (2-Pentanol) solution turns cloudy immediately, and/or phases separate: tertiary, such as tert-amyl alcohol (2-Methyl-2-butanol)
Question 3 : Explain how propyl ethanoate can be prepared in the laboratory.
In the experiment of preparing propyl ethanoate in the laboratory, the reaction will be performing by Fischer esterification. The general mechanism is pictured in Figure 1.
Figure 1. The overall reaction for Fischer esterification. The overall mechanism for a general acid and alcohol is depicted in Figure 2.
Figure 2. The general mechanism for Fischer esterification.
The overall mechanism follows the normal PADPLD. The acid catalyst is involved in the first step and regenerated in the last step. The first step is protonation of the carbonyl oxygen, followed by addition of the alcohol to form a tetrahedral intermediate. The third and fourth steps involve a proton transfer to form water, a good leaving group. After the water leaves in the fifth step, there is just the deprotonation of the carbonyl oxygen to form the neutral species. In your reaction, the synthesis of banana oil isopentyl acetate, you will be using isopentyl alcohol (3-methyl-1-butanol) and acetic acid (ethanoic acid, see Figure 3).
Figure 3. The overall reaction for this experiment
Experiment work Add 5 mL isopentyl alcohol, 7 mL glacial acetic acid, and a couple of boiling stones to a 25 mL round bottom flask. Add 0.5 mL of sulfuric acid with swirling to mix the solution. Attach the flask to a reflux condenser and heat the mixture to reflux for 60 minutes. After cooling to room temperature, transfer the contents to a large reaction tube. Add 15 mL of distilled water to the solution and stir. Let the layers separate. Remove the aqueous layer and discard. Wash the organic layer with 9 mL portions of a saturated sodium bicarbonate solution until it tests basic after removing from the reaction tube. Finally, wash the organic layer with 6 mL of a saturated sodium chloride solution. Dry the organic layer with anhydrous sodium sulfate for 10 to 15 minutes. Transfer the organic layer to a 10 mL flask, filtering it through a cotton plug. Final volume/weight and IR spectrum are recorded.
Question 4 : There are 2 unlabeled bottles of chemicals in laboratory in which one of the bottles is pentane and the other one is pentene. Suggest three chemical tests that can help you to determine which of the two bottles is alkane and alkene.
First test: Addition of bromine Hydrocarbons are colourless. While, bromine dissolved in water or trichloroethane solvent forms an orange (yellow/brown) solution. When bromine solution is added to both an alkane or an alkene, the alkane solution remains orange which means no reaction. However, the alkene decolourises the bromine as it forms a colourless dibromo-alkane compound. This is due to unsaturated molecules in alkenes, which allowed atoms can add to them via the C=C double bond, so a reaction occurs. Whereas, alkanes are saturated , which means there is no double bond and atoms cannot be added. Therefore, there is no reaction.
Second test: Alkenes can add hydrogen to form a saturated alkane molecule Alkenes will react with hydrogen gas over a nickel catalyst to produce margarine from vegetable oils.
Third test: Addition of water to make alcohols The alcohol ethanol can be made by passing ethene gas and water vapour over an acid catalystat 300 o C. This is an example of an addition reaction and a hydration reaction because it involves the addition of water to another molecule.
Question 5 : Explain how Tollens reagent, Fehlings solution and Schiffs reagent can be used to test aldehyde. State the observation of the reaction of aldehyde with each reagent.
Tollens' reagent is a chemical reagent most commonly used to determine whether a known carbonyl-containing compound is an aldehyde or a ketone. It is usually ammoniacal silver nitrate, but can also be other mixtures, as long as aqueous diamminesilver(I) complex is present. A positive test with Tollens' reagent results in elemental silver precipitating out of solution, occasionally onto the inner surface of the reaction vessel, producing a characteristic and memorable "silver mirror" on the inner vessel surface. Aldehydes will be positive in Tollen's test and a mirror-like material will be formed.
Ball-and-stick model of the diamminesilver(I) cation, [Ag(NH 3 ) 2 ] +
Fehling's also can be used to determine whether a carbonyl-containing compound is an aldehyde or a ketone. The bistartratocuprate(II) complex in Fehling's solution is an oxidizing agent and the active reagent in the test. The compound to be tested is added to the Fehling's solution and the mixture is heated. Aldehydes are oxidized, giving a positive result, but ketones do not react, unless they are alpha-hydroxy-ketones. The bistartratocuprate(II) complex oxidizes the aldehyde to a carboxylate anion, and in the process the copper(II) ions of the complex are reduced to copper(I) ions. Red copper(I) oxide then precipitates out of the reaction mixture, which indicates a positive result i.e. that redoxhas taken place (this is the same positive result as with Benedict's solution). A negative result is the absence of the red precipitate; it is important to note that Fehling's will not work with aromatic aldehydes; in this case Tollens' reagent should be used.
The Schiff test is relatively general chemical test for detection of many organic aldehydes. The unknown sample is added to the decolorized Schiff reagent; when aldehyde is present a characteristic magenta color develops. Fuchsin solutions appear colored due to the visible wavelength absorbance of its central quinoid structuresee also for example viologen but are "discolorized" uponsulfonation of the dye at its central carbon atom by sulfurous acid or its conjugate base, bisulfite.
This reaction disrupts the otherwise favored delocalizedextended pi-electron system and resonance in the parent molecule.
The structure of the "decolorized" Schiff reagent.