ACE WEEK 3 LESSON SUMMARY: Le eee ‘Alcohols are classified by the number of alky groups attached tothe carbon to ‘whieh the -OH functional group is bonded. (©. Primary alcohols (1") have t such alky! group. (© Secondary alcohols (2°) ave 2 such sky! groups. (0 Tertiary alochols (2°) have 3 such alkyl groups. ‘Combustion ofan alcohol ° (© Requires an inital input of energy (spark, fame) (© Complete combustion produces COs and H:O only. ‘© Incomplete combustion also produces C and CO, and less energy. Dehydration ofan acto: (0 Requires concentrated HsS0« catalyst and heat (© Can be considered the reverse reaction of hydration ofan akene. Substitution ofan alcoho: ° (© Requires aqueous acid catalyst, so HX is delivered in aqueous form. (© Reaction also benefits from ZnXs catalyst Oxidation of an alcoho 0. PRIMARY, © SECONDARY (© Requires an acid oxiising agent, |e, K:Cr,Oxel. HeSOx or KMaOvéi HiS0., and heat (Aldehydes wil futher exidge to the corresponding carboxylic acd (0 Tertiary alcohols do nat ten to oxidise, “Toname a carboxylic acid, drop the’ of the corresponding akane and replace with ‘cic acid .g, ethane ethanoic ci. “Tho oxidation of an alcohol can be wien as a redox reaction (© Toalance oxidation hai-equations in acidic media, ad H.0(), H"(ag) oF lectrons where necessary. ‘0 The reduction half-equations are available on the NESA data sheet. } ania bueenned es ota | ‘Another substitution reaction is possible for tertiary halaakane only: (© Requires heat. HSC CHEMMSTRY | ORGAN CHEMISTRY | THEORY - WEEKACE WEEK 3: REACTIONS OF ALCOHOLS EXTENSION: MARKOVNIKOV'S RULE FOR ADDITION REACTIONS NOTE: This is NOT in the HSC syllabus, but has been included because some schools teach and examine this content. ® * When unsaturated organic compounds undergo addition, there may be more than one product formed. + However, one product is usually produced in a greater proportion than i the other. Ww omounas R wy ‘ Hoe HoH Br ») Hero) Poked I I SBclgla erieaeas| cides? ols loc HOW OH ca) HoHO# ’ major product minor product The substance that is produced in greater quantities is the ‘major product’. ) + The substance that is produced in lesser quantities is the ‘minor product’ Markovnikov's Rule (Markownikoff’s Rule) states: In addition reactions involving an unsymmetrical alkene with a polar reagent (e.g. HX or H20), the hydrogen atom will bond to the carbon atom with a greater number of 9 hydrogens already attached to it. )) ‘+ If hydrogens were currency, one way to remember this is: “The rich get richer.” ‘© Carbons with more hydrogen atoms are “rich”; they will get more hydrogen atoms, i.e. “richer’ if possible. Inthe HSC Chemistry course, Markovnikov's Rule can be applied to ~ hydrohalogenation and hydration reactions. EXAMPLES Write structural equations, then indicate the major product: HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY - WEEK 31. Propene reacts with Hi(g) 2. Hydration of but-1-ene 3. 2-Methylbut-2-ene reacts with HBr(g). NOTE: PBC and Tutorial questions in all Module 7 booklets will not require knowledge of Markovnikov's Rule. For practice applying Markovnikov's Rule, refer to the Additional Practice Questions for this booklet and subsequent booklets in Module 7. For example, APQ Week 3 Q5 requires knowledge of this rule. HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY - WEEK 3ACE INQUIRY QUESTION: How can alcohols be produced and what are their properties? 7.41 INVESTIGATE THE STRUCTURAL FORMULAE, PROPERTIES AND FUNCTIONAL GROUP INCLUDING: = primary secondary = tertiary alcohols ALCOHOLS are organic compounds which contain the hydroxyl (OH) functional group. ‘* Alcohols can be classified based on the number of alkyl groups attached to the carbon to which the -OH functional group is bonded. ‘+ Primary (1°) alcohols have 1 carbon chain attached to the carbon adjacent to the -OH functional group. © The -OH functional group is on the terminal carbon. «Secondary (2°) alcohols have 2 carbon chains attached to the carbon adjacent to the -OH functional group. HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY - WEEK 3ee ace * Tertiary (3°) alcohols have 3 carbon chains attached to the carbon adjacent to the -OH functional group. EXAMPLES Identity the type of alcohol (primary, secondary or tertiary) H 4 @ n\ ks [on OH i ee HxC—C—C-—ch, i cm 4 4 Hy H | oH ‘hs i oH, Weeee se HO—C—cC—CHs CH. y | My CHy CH | HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY - WEEK 3ACE ICT 7.4.4 WRITE EQUATIONS, STATE CONDITIONS AND PRED! PRODUCTS TO REPRESENT THE REACTIONS OF ALCOHOLS, INCLUDING BUT NOT LIMITED TO (ACSCH128, ACSCH136): combustion dehydration substitution with HX oxidation 7.4.8 INVESTIGATE THE PRODUCTS OF THE OXIDATION OF PRIMARY AND SECONDARY ALCOHOLS COMBUSTION COMBUSTION of alcohols in oxygen produces CO: and H.0 in a highly exothermic reaction » * Combustion requires an initial input of eneray (spark, flame, etc.) to overcome the activation energy barrier. ‘* Recall that combustion can be complete or incomplete. © Complete combustion occurs when there is an excess of oxygen. All carbons in the alcohol are converted into arbon dioxide. oo © Incomplete combustion occurs when there is an oxygen deficiency. Some carbons are released as either carbon monoxide or soot. Lo > a © Incomplete combustion also produces less energy per mole than complete combustion. ») ‘* _Insituations in which the energy from combustion is being exploited to perform useful work, itis important to maximise complete combustion, e.g. in car engines. © For example, the combustion of propanol: HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY - WEEK 3AcE . DEHYDRATION DEHYDRATION of alcohols produces the corresponding alkene, and feleases water as the byproduct. ALCOHOL — ALKENE +420, * Dehydration of alcohols requires special conditions: © Concentrated H2S0, catalyst OR concentrated HsPOs Catalyst OR Al,0; catalyst. © Heat is also required to achieve a reasonable rate of reaction for primary and secondary alcohols. Dehydration of tertiary alcohols occurs rapidly at room temperature. - n of an alkene, bit note * Dehydration is the reverse reaction of hydrat the different reaction conditions. © The -H and -OH of the alcohol must be removed from two adjacent carbons such that a T-bond can form from the vacant molecular orbitals. For example, the dehydration of butan-1-ol | ee © For example, the dehydration of butan-2-ol: HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY - WEEK 3AcE SUBSTITUTION WITH HYDROGEN HALIDES ALCOHOLS can undergo SUBSTITUTION WITH HYDROGEN HALIDES (HF, HCI, HBr, Hl) to produce the corresponding halogenated haloalkane, and water as a byproduct. proven COFOL FPP FALOALKANE HIS” ‘+ Recall that hydrogen halides are compounds with the general formula HX, where X is. a halogen... + The hydroxyl group in alcohols can be substituted with the halogen in aqueous hydrogen halides to produce halogenated organic compounds, with water as the second product. © These reactions require aqueous acid catalysts, so therefore aqueous hydrogen halides (i.e. hydrohalic acids) are used and D)) not the gaseous hydrogen halides. © Another catalyst that is used is ZnXe where X is the halogen, ie. ZnCh if HCl(ag) is used. - NOTE: Do NOT confuse this with the addition of HX over a double or triple bond, where gaseous hydrogen halides are used instead, and not the aqueous forms. + Inorder of reactivity of alcohols in substitution reactions: tertiary > secondary > primary. + Inorder of reactivity with acids, Hi(aq) > HBr(aq) > HCl(aq) >> HF (aq). — ees © HF (aq) is not generally observed to substitute on alcohols «For example, the reaction between propan-2-ol and HBr(aq) » HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY -WEEK'3ACE " OXIDATION OXIDATION of alcohols occurs in the presence of strong oxidising agents. PRIMARY ALCOHOL — ALDEHYDE ~+ CARBOXYLIC ACID’ SECONDARY ALCOHOL="KETONE a Recall that oxidation involves the loss of electrons, and always occurs in conjunction with the reduction of another species, which involves the gain of electrons. ‘* The oxidation of alcohols requires special conditions: © Acidified oxidising agent: acidified potassium dichromate (KeCr,07, dilute H2SO.) or acidified potassium permanganate (KMnOs, dilute H2SO,). © Heat ‘+ To determine the product of the oxidation of alcohols, the type of alcohol involved must be considered, | © Aldehydes are the first product of primary alcohol oxidations because the hydroxy! group is located on a terminal carbon. © This will result in the newly formed carbonyl group also being located on a terminal carbon, classifying the compound as an aldehyde. «For example, the oxidation of ethanol: HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY - WEEK 3Ace " EXTENSION: Producing aldehydes from oxidation of primary alcohols ‘Stopping the oxidation reaction of a primary alcohol at the aldehyde is rather difficult, since aqueous oxidising agents will oxidise the aldehyde further to produce the carboxylic acid. © There are a few ways to produce more of the aldehyde: ° agent to carry out a second oxidation, © The aldehyde can be distilled from the reaction mixture as it is formed. * However, both of these methods are not great, and the final mixture will have some aldehyde and carboxylic acid both present. * In industry, DMSO-oxalyl chloride would be used to oxidise a primary alcohol to an aldehyde, with excellent yield and a short “ reaction time. ») © For secondary alcohols, the hydroxyl group is attached to a noi © The newly formed carbonyl group will be attached to two separate alkyl groups, and this compound will be classified as a ketone. » «For example, the oxidation of butan-2-o 8 &T,oo_,.| _———_—_ HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY - WEEK 3ACE © With primary and secondary alcohols, the oxidising ager.. removes a hydrogen from both the hydroxyl group and the associated carbon atom such that a double carbon-oxygen bond can be formed OVERVIEW OF IUPAC NOMENCLATURE FOR CARBOXYLIC ACIDS «The IUPAC nomenclature conventions for carboxylic acids will be covered in more detail in Week 5, ‘+ Insummary, a carboxylic acid is characterised by the -COOH (carboxyl) functional group: Thee’ in the name of the corresponding alkane is dropped and replaced by ‘oic acid’, ° HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY - WEEK 3ACE “ REDOX CHEMISTRY FOR THE OXIDATION OF ALCOHOLS * The oxidation of alcohols is a redox process which can be written as a redox equation. * To balance oxidation half-equations in acidic media: 1. Balance the number of atoms which are not H or O on both sides of the equation 2. Balance the number of O atoms by adding H20(() to the side of fewer O atoms. 3. Balance the number of H atoms by adding H"(aq) to the side of fewer H atoms, 4. Balance the charge by adding electrons to the right side. '* The reduction half-equation will be that of MnOy or Cr20;? depending cn the oxidising agent chosen. This is provided on the NESA Data Sheet % Cr.07*(aq) + 7H"(aq) + 3” + Cr*(aq) + 7/2 H2O() MnO. (aq) + 8H"(aq) + 5e'(aq) — Mn?*(aq) + 4H.0(/) ‘* Write the full redox equation by summing the oxidation and reduction half-equations so that no electrons remain in the final equation © Ensure to cancel out any common H*(aq) or Hz0(/) on both sides of the equation. EXAMPLE 1 Write a full redox equation to demonstrate the oxidation of butan-2-ol with acidified dichromate. EE Pees ee eS ee ee Sn ee en EXAMPLE 2 Wiite a full redox equation to demonstrate the oxidation of ethanal with acidified permanganate. Se — Oe SE ee HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY - WEEK 3 »ACE 8 7.45 INVESTIGATE THE PRODUCTION OF ALCOHOLS, INCLUDING: Substitution reactions of halogenated organic compounds NOTE: Unlike the other reactions learned today, this reaction produces an alcohol. Here, the alcohol is not a reactant. SUBSTITUTION OF HALOGENATED ORGANIC COMPOUND AHALOGENATED ORGANIC COMPOUND may undergo substitution with a metal hydroxide to produce an alcohol and a salt as a by-product. HALOALKANE + DILUTE NaOH — ALCOHOL + SALT + Substitution of a halogenated organic compound with a metal hydroxide requires special conditions: ite NaOH in acetone solvent: dilute NaOH is required since concentrated NaOH will promote a different reaction instead © Heat since the reaction will be very slow without it. EXTENSION: Purpose of the acetone solvent The acetone (propan-2-one) solvent promotes this substitution reaction by forming stronger ion-dipole interactions with the Na* ion. * This leaves the OH’ exposed and ready to attack the haloalkane, since the & charge on the O from acetone is more exposed than the 5° on the carbon atom. «For example, the substitution of 1-bromoethane to produce an alcohol. HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY - WEEK 34 AcE 6 In particular, TERTIARY HALOALKANES can undergo substitution with water to produce an alcohol and a hydrogen halide as a by-product. TERTIARY. HALOALKANE + H:0 + TERTIARY ALCOHOL + HX" * This reaction wil work of or primary haloalkanes. ly for tertiary hi alkanes, and not secondary * Note that heating with dilute NaOH in acetone solvent will also produce a tertiary alcohol * For example, the substitution of 2-bromo-2-methylpropane to produce an alcohol: KEY POINTS: Reactions concerning alcohols Reaction ee Inorg. carne Reactant | Conditions | Org. Product | pryicos ‘Combustion of alcohol De spatk ue C02, HzO Dehydration Cone. ofatconot | “A | H,S0s,heat| — AlKene H.0 ‘Aqueous Substitution | 4x(aq)_| acid, heat, | Haloalkane H.0 of alcohol ZnX. 3 Acidified | 1° — aldehyde Oxidation of | KMnO, or with dil. — carboxylic HO alcohol KeCrO; | H2SO.(aq), acid (sometimes) heat (2° — ketone ‘Substitution Acetone of Dil. NaOH | solvent, Alcohol Salt haloalkane heat Substitution Tertiat ry | Hydrogen of tertiary 20 Heat hoheed alcohol halide End of Theory HSC CHEMISTRY | ORGANIC CHEMISTRY | THEORY - WEEK 3HSC CHEMISTRY ORGANIC CHEMISTRY PROBLEM BASED CLASS - WEEK 34. Classify the following alcohol. CH, H Primary Secondary Tertiary Quaternary com> N Identify the product of the reaction between propan-1-ol and hydrochloric acid with a zinc chloride catalyst. Propanoic acid 4-chloropropane 1-chloro-2-hydropropane No reaction occurs gom> s Name the following tertiary alcohol. CH;CHs Pentan-3-ol 1-methylpropan-2-o1 3-methylpentan-3-ol Diethyimethan-1-ol 9op> An alcohol is added to a very large excess of hot dilute H2S0,(aq) and K2Cr20-(aq). Subsequently, the major organic compound from the final mixture is extracted. Which of the following is NOT a possible identity of this compound? Aldehyde Ketone Carboxylic acid Tertiary aleohol GOR> Se HSC CHEMISTRY | ORGANIC CHEMISTRY | PBC- WEEK 3 1 mark | 4 mark 1 mark 4 markACE 0 Consider the following reaction scheme. A - F are 6 marks unique organic compounds. A branched arrow indicates that two products are possible; otherwise, all other reactions yield one product only. ito ow 1a excees oxidant i] passe ro pecan ott on, ite NaOHiag) excess oxidant ‘acetone Identify the IUPAC systematic names of compounds A-F, providing reasons.6. The reaction scheme below shows the reactions of 5 mark the organic compounds A, B, C, D and E. Additional non-organic reagents and reaction conditions are written on the reaction arrows, and branched arrows indicate that more than one product is possible. Single arrows indicate only one possible product is formed. As we Ko er bl evcess ae DO _.Feren000H! “ye Lt t H;S0, heat eos, e } ower te Identify the full structural formula of compounds A- E, justifying your answers with reference to the information provided. HSC CHEMISTRY | ORGANIC CHEMISTRY | PEC- WEEK 37. Eric has a sample of bromoethane, which he wishes 4 marks: to convert into ethane. Draw a flowchart to demonstrate a possible reaction scheme he may undertake, End of Problem Based Class HSC CHEMISTRY | ORGANIC CHEMISTRY | PBC -WEEK3= Cr HSC CHEMISTRY ORGANIC CHEMISTRY TUTORIAL - WEEK 3Ace a 1. Which of the following types of alcohols is resistant 4 mark to oxidation by acidified potassium permanganate? Primary alcohol Secondary alcohol Tertiary alcohol Quaternary alcohol go> 2. Jay heats an alkene with dilute aqueous sulfuric 4 mark acid to form one new product in an aqueous solution. What should Vanathy do if she wants to reverse Jay’s reaction? ‘A. Heat Jay's aqueous product with dilute aqueous sulfuric acid catalyst for a longer period of time, and higher temperatures. B. Heat Jay’s aqueous product with concentrated phosphoric acid catalyst. C. Heat Jay's aqueous product with dilute aqueous sulfuric acid and mercury sulfate catalyst D. Vanathy cannot reverse Jay's reaction 3. Classify and name the following alcohol. 4 mark HH CyH, H [eel H—C—C—C—H Le olenl H OH H Secondary, propan-2-ol Tertiary, 2-methylpentan-2-ol ‘Secondary, 2-propylpropan-1-ol Tertiary, 2-propylpentan-1-ol 99@> HSC CHEMISTRY | ORGANIC CHEMISTRY | TUTORIAL - WEEK 3ACE 2 4. Which of the following reaction conditions is most 4 mark Suitable for the following chemical conversion? HoH OH omnes Gl Hu wi—ttin ate pel hal oeg | | Aad Add A. HCI(g) and UV light B. — Ch(g) and UV light C. HCl(aq) only D. Clx{aq) only 5. Hydration reactions are used to produce alcohols [4 mark from alkenes or substituted alkenes. Which of the following alcohols could NOT have been a product of such a hydration reaction? A. 8. Hcl OH wu wed deod ay Heel Ae on GI D. HocoH on a Hote HOH Gl CHy H HSC CHEMISTRY | ORGANIC CHEMISTRY | TUTORIAL - WEEK 3ACE DOm> a Ross has a sample of the following organic Arik molecule: He devises a series of reaction steps as below, and calls it a Ross-cycle: 1. Heat with dilute aqueous sulfuric acid for 30 minutes. 2. Separate the sulfuric acid from the organic mixture, and then keep only the organic mixture. 3. Tothe organic mixture, heat with concentrated sulfuric acid for 30 minutes. 4. Separate the sulfuric acid from the organic mixture, and then keep only the organic mixture. If Ross repeats this entire series of steps again, he will have conducted two Ross-cycles. After a certain number of Ross-cycles, he detects this organic molecule in his mixture: What is the minimum number of Ross-cycles that may have been conducted? 2 3 4 5 HSC CHEMISTRY | ORGANIC CHEMISTRY | TUTORIAL - WEEK 3ACE z 7. Justin is presented with two unlabelled test tubes containing propan-1-ol and 2-methylpropan-2-ol. To distinguish between the two alcohols, Justin mixes a sample of each alcohol with excess acidified potassium dichromate(IV). Crz0;* ions are orange in colour, and if they are reduced to Cr* ions, the solution would turn green. The half-reaction for this reaction is: Cr0;"(aq) + 14H"(aq) + 6e — 2Cr°*(aq) + TH20(N) After a long period of time, Justin observes the following colours: A 8 Green Orange a. Identify A and B and justify your choice. “A marie: HSC CHEMISTRY | ORGANIC CHEMISTRY | TUTORIAL - WEEK 3ACE 2 b. Write a structural equation to represent any — | 2 marks reactions that may have occurred. ¢c. Write a balanced redox equation to represent the | 2 marks first step of oxidation in part b HSC CHEMISTRY | ORGANIC CHEMISTRY | TUTORIAL - WEEK 38. Consider the following flowchart below. The molecular formulae are provided for organic compounds A, B, C and D. The numbers 1, 2 and 3 contained within dotted circles represent reaction conditions, including any non-organic reagents. Itis known that compound D undergoes an oxidation reaction to form a ketone. B D_|_oxidation CothBr cso [| Ketone A CoHe c CohtyBr Hint: You will need to revise the reactions that you learned in Week 2. a. Draw full structural formulae and provide the 4 marks IUPAC systematic names of compounds A, B, C and D justifying your answer with reference to the information provided. HSC CHEMISTRY | ORGANIC CHEMISTRY | TUTORIAL - WEEK 3b. Identify the reactants and conditions required for reactions 1, 2 and 3, and identify the types of reactions they are. HSC CHEMISTRY | ORGANIC CHEMISTRY | TUTORIAL - WEEK 3 20 3 marks9. Draw a flowchart or series of reactions detailing the 4marks intermediate steps required for the following chemical conversion: CH ——_» 4c —c_—C__on go z—o—z 4 | | A Hint: You will need to revise the reactions that you learned in Week 2. End of Tutorial HSC CHEMISTRY | ORGANIC CHEMISTRY | TUTORIAL - WEEK 3ACE 1. Correctly identify the name and classification of this Py 1 mark molecule. OH HjC—C—CHy CH; A. Primary, propan-2-ol B. Secondary, propan-2-ol C. Tertiary, 2,2-dimethyipropan-1-ol D. Tertiary, 2-methylpropan-2-ol 2. Identify the product formed when acidified Teac potassium permanganate is added to octanal. a A. Octan-t-one y B. — Octanalic acid C. Octanoie acid D. — Octacarboxylic acid 3. The following flowchart represents a series of 7 marks. organic reactions. Note that A - G are different organic compounds. D canoe) PAC plored aanwon ar eon: cone. HS0, Pac ‘-chloropropane a}—— B : ce , Identify and draw the structures of A - G. HSC CHEMISTRY | ORGANIC CHEMISTRY | APO - WEEK 3Ace Under low oxygen conditions, the following reaction takes place with the following states: CeHsOH(/) + 902(g) —- 4C0,(g) + 2CO(g) + 2C(s) + 9H20(N) 36 a. Describe the reaction that is taking place, and 3 marks explain the need to monitor this process. b. Calculate the total volume of ; vu gas evolved at 2 marks 50.0°C and 101.3 kPa if 100.0 g of ColtsrOH(0 is consumed in this manner. 5. Consider the reaction flowchart below. but-t-yne ‘Compound A ‘Compound 8 Conan 5 Compound G 2.chiorobutane a. Draw the structures and provide the IUPAC | 6 marks names of compounds A, B and C, and identify the reaction conditions 1, 2, and 3. b. Explain why the reaction from Compound A under 2 marks Fe se eh a a a Conditions 2 produces one major product (Compound B) and one minor product. Myrcene is an unsaturated hydrocarbon with only 5 marks C-C, C-H and C=C bonds which can be found in the leaves of bay trees. During an experiment, a 2.00 g sample of pure myrcene reacted with exactly 1050 mL of hydrogen gas measured at 20°C and 101.6 kPa. In this reaction, the myrcene was fully converted into decane. Determine the molecular formula of myrcen Oe End of Additional Practice Questions HSC CHEMISTRY | ORGANIC CHEMISTRY | APQ-WEEK 3ace . PROBLEM BASED CLASS 3 QUICK SOLUTIONS Av B B ic A ae en A: but-1-ene, B: 2-chlorobutane, C: 1-chlorobutane, D: butan-2-ol, E: butan-1-ol, F: butanoie acid 6. : propyne, B: propan-2-one, C: propene, D: propan-1-ol, E: propan-2- ol TUTORIAL 3 QUICK SOLUTIONS ic Nee een a >>r>oOooa A: propan-1-ol, B: 2-methylpropan-2-01 » b. Cr20;*(aq) + BH"(aq) + 3CaHzOH(aq) —> 2Cr**(aq) + 7H0(/) + 3CsHeO(aq) Ba A: propane, B: 2-bromopropane, C: 1-bromopropane, D: propan-2-0l. Sea ADDITIONAL PRACTICE QUESTIONS 3 QUICK SOLUTIONS 1.0 2.06 4b, 122L Bsf) 5.6. ‘A: but-1-ene, B: butan-2-ol, C: butan-2-one 6. Cote ee reg Ree oe HSC CHEMISTRY | ORGANIC CHEMISTRY | SOLUTIONS - WEEK 3