Assignment CHM301 AS1204D Group 3 PDF

Preview

Summary

Assigment inorganis chemistry chm301...

Description

ASSIGNMENT CHM 301 ORGANIC CHEMISYTRY II

GROUP MEMBERS: 1. NURUL FADHILA BINTI MD REJAB (2019437346) 2. NUR QAMARINA BINTI MOHD NAZAR (2019402828) 3. NURUL AYU NATASHA BINTI MAT RANI (2019248332) CLASS: AS120-4D GROUP: 3 TITTLE: ALCOHOL, ALDEHYDE AND KETONE. LECTURER’S NAME: MADAM ZURHANA MAT HUSSIN DATE SUBMIT: 20 JUNE 2021

1. Alcohol is widely used in many industries as solvent, fuel, chemical feedstock, antiseptic, and others. List three (3) alcohols and its uses from different type of industries. For each of alcohol briefly explain ALCOHOLS: ● Ethanol Uses: -Can be used as a fuel and gasoline additive. - Can be used as an antifreeze. - It used as a solvent in the production of perfumes, paints, and tinctures. - As a disinfectant and in tinctures for example tincture of iodine. - Contain in many alcoholic beverages, such as beer, wine, and distilled spirits as an intoxicating ingredient.

● Phenol Uses: - Phenol used in pharmaceutical industry as antioxidants, antiseptic agents, chemical intermediates, disinfectants, and many more. - On the other hand, in manufacture industry, phenol used as tanning agents, rubber, epoxy, polycarbonate plastic resins, paper and carbolic soap. - In a cosmetic and personal care, phenol used as hair spray and in many cosmetic products such as lotion, and acne medication.

● 1-propanol Uses: - 1-propanol often used as a multi-purpose solvent in industry and in home. - used as solvent in pharmaceutical industry, mainly for resins and cellulose esters and disinfecting agent. - It is used in flexographic printing ink and textile applications - Products for personal use, such as cosmetics and lotions, and in window cleaning, polishing and antiseptic formulations.

A) Industrial or lab scale for the preparation of the alcohols 1. Alcohol: Ethanol Ethanol is produced on an industrial scale using hydration of ethene. Ethanol is manufactured in large quantities because it is a valuable intermediate in the production of organic compounds. Ethanol is created when ethene (𝐶𝐻2 =𝐶𝐻2 ) is hydrated. This is the simplest and most cost-effective method of producing ethanol. Ethene is a petroleum industry byproduct that is readily available as a raw material. The reaction takes place in the presence of a catalyst, phosphoric acid (H3PO4). Silicon dioxide is coated in phosphoric acid. In a fixed molar ratio of ethene/water (1:0.60), ethene is mixed with steam. The gases react over the catalyst to form ethanol when the mixture is heated to 300°C. The liquefaction of ethanol occurs when the gaseous mixture of unreacted ethene and product ethanol is cooled. The unreacted ethene is recycled back into the reaction chamber after the product has been separated. Depending on the activity of the catalyst, productivity per cycle (or per pass) ranges from 5.0 to 25.0 percent. By recycling ethene and removing ethanol from the reaction system, a high yield is achieved. The chemical formula is as follows:

2. Alcohol: Phenol Phenols can be prepared from benzene sulphonic acid. Firstly, at high temperature, benzene sulphonic acid mixed with melted sodium hydroxide. The formation of sodium phenoxide can be triggered from the mixture. Next, sodium phenoxide undergoes acidification with aqueous acid, such as H₃O⁺, resulting phenol.

Source: https://www.cliffsnotes.com/study-guides/chemistry/organic-chemistry-ii/phenols-and-arylhalides/synthesis-ofphenols#:~:text=In%20this%20process%2C%20benzene%20sulfonic,aqueous%20acid%20to%20yield%20p henol

Phenols also can be prepared from cumene, which obtained by Friedel-Crafts alkylation of benzene with propylene. In the presence of oxygen, cumene oxidated to produce cumene hydroperoxide, which treated with dilute acid to obtain phenol. However, phenols produced need to undergo purification as acetone also produced as one of the by-products.

Source: https://byjus.com/chemistry/phenol-preparation/#:~:text=1.,Preparation%20of%20Phenols%20from%20Haloarenes,phenoxide%20on%20acidification%20gives%20phen ol

3. Alcohol: 1-propanol 1-propanol is manufactured by catalytic hydrogenation of propionaldehyde. Propionaldehyde is produced via the oxo process by hydroformylation of ethylene using carbon monoxide and hydrogen in the presence of a catalyst such as cobalt octacarbonyl or a rhodium complex.

H2C=CH2 + CO + H2 → CH3CH2CH=O CH3CH2CH=O + H2 → CH3CH2CH2OH

A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide with moist Ag2O. When alkyl halide, n-propyl iodide is boiled with moist silver oxide, it undergoes hydrolysis to form alcohol, which is 1-propanol.

B) The properties/functions of the alcohol towards its uses 1. Alcohol: ethanol The properties of the ethanol towards its uses are as follows, the boiling point of pure ethanol is 78.5° C. It is flammable and colorless liquid. Since ethanol is flammable, it can be used as a fuel and burns cleaner than most other fuels. Ethanol also has a higher-octane number than gasoline, making it ideal for blending. Gasoline with a minimum octane number prevents engine knocking and ensures drivability. To achieve the standard 87 octane, lower-octane gasoline is blended with 10% ethanol. Next, it can be used in antifreeze products due to its low melting point of -114.5° C. It has a pleasant whiskey-like aroma to it. It also has a density of 789 g/l, which is 20% less than water. It is a good solvent that is easily soluble in water and is used in perfumes, paints, and tinctures. A disinfectant solution containing 70-85% ethanol kills organisms by denaturing their proteins and dissolving their lipids; it is effective against most bacteria and fungi, as well as many viruses, but not against bacterial spores. Because of ethanol's disinfectant properties, alcoholic beverages can be stored for a long time.

2. Alcohol: Phenol Phenol has molar mass of 94.11 g/mol and density of 1.07g/cm³. Its melting point is 40.5°C and boiling point at 181.7°C. Phenol usually is a weak acid. Due to its ability to form hydrogen bonds with water, phenol is considered as soluble in water, which is 8.3g in a 100mL. Pure phenol is a white crystalline solid and it is pink or red in colour if in impure state. Impure phenols influence the colour of carbolic soap which is deep pink, or red. Carbolic soap is a mildly antiseptic soap that contains carbolic acid (phenol) which derived from coal tar. Other than that, phenols are relatively more acidic in nature than other alcohols. It is said that phenol is 100 million times more acidic than cyclohexanol. The acidic feature of phenol helps to make it a better antiseptic agent. Moreover, phenol is said to be a good hydrogen donor which can stop reaction of free radicals, making it an antioxidant.

3. Alcohol: 1-Propanol The properties and functions of the 1-propanol towards its uses are, first, Physical properties of 1-propanol are it appears as a clear liquid with a sharp musty odour like rubbing alcohol. The boiling point of 1-propanol is 97°C. The solubility in water of 1-propanol is miscible. Due to its high solubility, its used in flexographic printing since its help maintain the solubility of ink resins too. Its vapor pressure is 1.99kPa at 20°C. While the chemical properties are, 1-propanol have a high-octane number which is RON 118, so its suitable for engine fuel usage. However, it is too expensive and RON 95 and 97 is the commercial one. 1-propanol have high volatility and rapid effect in killing gems such as bacteria, so it is often used as disinfectant like hand sanitizer and antiseptic.

C) a stepwise mechanism by using elimination after treatment with strong acid. ALCOHOL: • Ethanol

• Phenol

• 1-propanol

D) A chemical test to identify the alcohol. The three alcohols chosen can be identified by using ferric chloride test. In this test, phenol will react when added to ferric chloride solution, changing the colourless solution to violet. This result caused by the acidic feature of phenols and the formation of coloured coordination compound. On the other side, ethanol and 1propanol are the primary alcohols, which are less acidic than phenol. As the result for ferric chloric test, ethanol and 1-propanol remain unreactive and did not show any colour changes. However, if we heated the mixture, a redox reaction may occur between the alcohol and FeCl₃. The chemical reaction between phenol and ferric chloride as shown below:

Source: https://www.toppr.com/ask/question/phenol-gives-characteristic-colouration-with/

Other than FeCl₃ test, bromine test also can be conducted to distinguish between alcohols and phenol. Bromine water is said to recognize the presence of unsaturated. Ethanol and 1-propanol are the aliphatic alcohols which are saturated while phenol is the aromatic alcohol and is

unsaturated. As the result for this test, phenol will be decolorized and produce white precipitate. The alcohols will have no change in colours.

Source: https://chemistry.stackexchange.com/questions/90414/halogenation-of-phenol

2. Suggest three structural chemical formula of carbonyl compound (ketone/aldehyde) from natural (plant/animal) or synthetic sources. For each carbonyl compound ALDEHYDES: • Benzaldehyde BENZALDEHYDE’S STRUCTURE:

(From bitter almonds-plant)

• Acetone (2-Propanone) Acetone is known as a naturally occurring compound which composed of carbon, hydrogen, and oxygen. It came from plants, the breakdown of body fats and volcanic gases.

Source: https://chem.nlm.nih.gov/chemidplus/rn/67-64-1

• Acetaldehyde (Ethanal) Acetaldehyde or its common name is Ethanal, is an organic compound with the formula C2H4O. Its structure is:

a) describe the stepwise mechanism of nucleophilic addition with

H2O/HCN/Grignard reagent (choose only one) to produce derivatives of the carbonyl compound. • Benzaldehyde

• Acetone (2-PROPANONE) The stepwise mechanism of nucleophilic addition with HCN

• Acetaldehyde The stepwise mechanism of nucleophilic addition with Grignard Reagent

b) Propose four chemical reactions (reduction, oxidation, and condensation). ALDEHYDES: • Benzaldehyde i. Reduction Catalytic reduction:

Wolf-Kishner reaction:

ii. Oxidation

iii. Condensation Condensation with hydroxylamine (𝐶𝐻2 𝑂𝐻):

• Acetone

i. Oxidation Ketones are hard to oxidize because the absence of hydrogen atom attached to their carbonyl. It is said that only oxidation between ketone and strong oxidizing agent like potassium permanganate and potassium dichromate can occurs. The chemical reaction is as shown below:

ii.

Reduction - Reduction to Alcohols

Ketones can be reduced to 2° alcohols. Example of chemical reactions:

-

Clemmensen reduction to Alkane

Refluxing ketones with almagamated zinc in concentrated HCl reduces the compound to alkanes. Example:

iii.

Condensation

-

With ammonia

The product of this reaction is imine. Example:

• Acetaldehyde i. Reduction Acetaldehyde to ethanol

ii. Oxidation Ethanol to Acetaldehyde

iii. Condensation Acetaldehyde undergo aldol condensation

c) Briefly explain two chemical tests which can be used to identify the formation of this compound as aldehyde or ketone. ALDEHYDES: • Benzaldehyde Two chemical tests which can be used to identify the formation of benzaldehyde as an aldehyde are Tollen’s test and Brady’s test. In Tollen’s test the reagent and condition that was used is ammoniacal silver nitrate solution. The precipitation of elemental silver, which often produces a characteristic "silver mirror" on the inner surface of the reaction vessel, indicates a positive test with Tollen's reagent. This test yields a positive result for benzaldehyde, indicating the presence of an aldehyde functional group. Meanwhile in Brady’s test the reagent and condition that was used is a solution of 2,4-dinitrophenyl hydrazine (2,4-DNPH) in methanol and sulfuric acid at room temperature. The formation of yellow-orange precipitate indicates a positive test with Brady’s test. In this test, benzaldehyde gives a positive result as there is the formation of orange precipitate at the end of the reaction. Thus, this indicates that aldehyde functional group is present in benzaldehyde.

• Acetone Firstly, Fehling’s test can be used to distinguish between aldehyde and ketone. Fehling’s solution prepared from mixing Fehling’s A, blue copper (II) sulphate pentahydrate crystals solution and Fehling’s B, aqueous potassium sodium tartrate. When aldehyde reacts with Fehling’s solution, it will be reduced to acids and produces red precipitate. Meanwhile acetone, which is a ketone, will not react with Fehling’s solution and did not have any change in colour. Next is the sodium nitroprusside test which is benefit to recognize the presence of ketones. Sodium nitroprusside test can be conducted by mixing sodium nitroprusside with acetone and shake well until the colour changes. The reaction between acetone and alkali will gives an anion that will reacts with sodium

nitroprusside to form a red solution. A red solution means that it is a positive result for this test. However, aldehyde will not yield a positive result from this test.

• Acetaldehyde The first test is The Tollens’ test can be used to distinguish between aldehydes and ketones. It is a reaction test since aldehydes will be oxidized into a carboxylic acid while ketones cannot. Tollen’s reagent, is an alkaline solution with a mixture of silver nitrate and ammonia that oxidizes the aldehyde to a carboxylic acid. Acetaldehyde is an aldehyde. So, the Tollen’s reagent will react acetaldehyde to form silver mirror precipitate. Next test is Fehling’s test. It is solution that prepared by combining two solution, Fehling’s A, which is a deep blue aqueous solution of copper (II) sulfate, and Fehling’s B, which is a colourless solution of aqueous potassium sodium tartrate (Rochelle Salt). Acetaldehyde will be added to Fehling’s solution and the mixture is heated. Since acetaldehyde is an aldehyde, it will be oxidized. Ketones does not react with Fehling’s test, so acetaldehyde is an aldehyde. Aldehyde do react with both Tollen’s and Fehling’s test while ketones not, this is because ketones does not have a H atom that directly bonded to a carbonyl group which can be oxidized.

REFERENCES 1. Adam, C. (2018). Ethanol fuel basics. Retrieved June 07, 2021, from https://afdc.energy.gov/fuels/ethanol_fuel_basics.html#:~:text=Fuel%20Properties&te xt=Ethanol%20has%20a%20higher%20octane,attain%20the%20standard%2087%20 octane 2. Austin, G. (2021, April 13). Production of ethanol: A-level chemistry revision notes. Retrieved June 03, 2021, from https://alevelchemistry.co.uk/notes/production-ofethanol/ 3. Britannica. (2020). Ethanol. Retrieved June 07, 2021, from https://www.britannica.com/science/ethanol 4. CHM301 – Organic Chemistry II notes, UiTM. 5. Colin Baker. (2007) The silver mirror test. Retrieved from June 10, 2021 from https://edu.rsc.org/exhibition-chemistry/the-silver-mirrortest/2020077.article 6. David,

P.

(2018).

Ethanol

molecule.

Retrieved

June

03,

2021,

from

https://www.worldofmolecules.com/fuels/ethanol.htm#:~:text=Pure%20ethanol%20is %20a%20flammable,less%20than%20that%20of%20water. 7. Ethanol:

Uses.

(2012).

Retrieved

June

07,

2021,

from

https://www.infoplease.com/encyclopedia/science/chemistry/organic/ethanol/uses 8. Harpercollege. (2021) Functional Groups – Aldehydes and Ketones. Retrieved June 10, 2021 from http://dept.harpercollege.edu/chemistry/chm/100/dgodambe/thedisk/qual/9 back6.htm 9. Hazwani, N. (2011, March 14). Production Of Phenols. 10. Jove publisher. (2021) Identification of Unknown Aldehydes and Ketones | Protocol. Retrieved on June 10, 2021 from https://www.jove.com/scienceeducation/11222/identification-of-unknown-aldehydes-andketones#:~:text=carbonyl%2Dcontaining%20compound.,Tollens%20Test,aldehyde%20to%20a%20carboxylic%20acid

11. Kevin, A. B. Chapter 3 – Alcohols, Phenols, and Ethers. Angelo State University. 12. L. G. Wade, J. W. Simek, Organic Chemistry Ninth Edition. 13. National Center for Biotechnology Information (2021). PubChem Compound Summary for CID 180, Acetone. Retrieved June 9, 2021 from https://pubchem.ncbi.nlm.nih.gov/compound/Acetone. 14. Vedantu Learn Live Online. (2021) When Alkyl Halide is Heated with Dry Ag2O. Retrieved on June 10, 2021 from https://www.google.com/url?sa=t&source=web&rct=j&url=https://www.vedan tu.com/question-answer/alkyl-halide-is-heated-with-dry-ag2o-it-producesclass-12-chemistry-cbse5f91064975777a42e459b05a&ved=2ahUKEwiMiu6om5zxAhX3xDgGHSR4BkQFjAPegQIIRAF&usg=AOvVaw1Dx4dw2fBVJ-Mr_2s653H7 15. WE Benet. (2011) The mechanism of the reaction of the Tollens reagent. Retrieved Jun 10, 2021 from https://journals.sagepub.com/doi/pdf/10.3184/174751911X13206824040536...