ORGANIC CHEMISTRY (18M)

I.DISTINGUISH TESTS OF ORGANIC COMPOUNDS: SL.NO

Name of the test Neutral ferric chloride Sodium bicarbonate Iodo form test Lucas test Hinsberg test Carbylamines test Sodium metal test 2,4 DNP test Tollens test Fehilings test

Identification of compounds Only phenols(violet or purple color) Only carboxylic acid(brisk effervescence) All 2-ketones,2-alohols,ethanal,ethanol(yellow color crystals) To distinguish10 20 & 30 alcohols 10 20 &30 amines Only primary amines Alcohols(effervescence) Both aldehydes & ketones (yellow color crystals) Only aldehydes(silver mirror formation) Only aldehydes(red ppt)

01 02 03 04 05 06 07 08 09 10

Named Reactions:
1. Aldol Condensation: condensation between two molecule of an aldehyde or a ketone having atleast one -hydrogen atom to form a -hydroxyaldehyde or a hydroxyketone is known as aldol condensation.

Aldol condensation takes place in presence of dil base. 2. Cannizzaro Reaction: The disproportionation (self-redox) of aldehydes lacking hydrogen atom (as C6H5CHO, HCHO, R3C.CHO etc.) in presence of strong base to form salt of an acid & a primary alcohol is known as Cannizzaro reaction.

3.

Carbylamine test: When a primary amine is heated with alcoholic caustic potash and chloroform, an offensive smelling compound called carbylamine ( alkyl or arylisocyanide) is formed.

4.

Clemmension Reduction: The reduction of >C=O group to methyl group (>CH2) with amalgamated zinc and conc. HCl is known as Clemmension reduction.

5.

Wolf-Kishner reaction: A carbonyl compound on heating hydrazine and pottassium hydroxide(KOH)in a high boiling polar solvent such as ethylene glycol,gets reduced to give a hydrocarbon.

6.

Esterification Reaction: Reaction of an alcohol with a carboxylic acid in the presence of a small quantity of conc.H2SO4 to form an ester is called esterification.

Esterification process is generally reversible. 7. Finkelstein Reaction: Alkyl iodides can be prepared by the reaction of alkyl chlorides/ bromides with NaI in dry acetone.

8.

Gattermann Reaction: Gattermann reaction is used for obtaining chlorobenzene or bromobenzene from benzenediazonium chloride by treating it with Cu/HCl or Cu/HBr respectively.

9.

Gattermann-Koch Reaction: When benzene or its derivative is treated with carbon monoxide and HCl in the presence of anhydrous aluminium chloride or CuCl, it gives benzaldehyde or substituted benzaldehyde.

10.

Iodoform test: The compound containing methyl group bonded to carbonyl group (CH3-CO-) or (CH3-CH.OH-) reacts with aquous NaOH and iodine solution gives yellow ppt of Iodoform.

11.

Hell-Volhard-Zelinsky Reaction: When aliphatic carboxylic acid containing hydrogen are reacted with chlorine or bromine in presence of small amount of red phosphorous, the corresponding -haloacids are obtained.

12.

Hinsberg Test: Hinsberg test is employed to distinguish primary, secondary and tertiary amine. The reagent used in this test is benzene sulphonyl chloride. The tests are: a) Primary amine:- It gives sulphonamide with hinsberg reagent, this sulphonamide is soluble in NaOH or KOH. B) Secondary amine:-With hinsberg reagent,it forms sulphonamide, which is insoluble in NaOH or KOH. C) Tertiary amine:- Tertiary amine do not react with hinsberg reagent ,because it is not having replaceable hydrogen. Hoffmann-Bromamide Reaction: When an amide is heated with bromine and an alkali, a primary amine containing one carbon less than the amide is obtained. This reaction is called Hoffmann-Bromamide reaction. This reaction is very useful for converting a higher homologue to next lower one.

13.

14.

Kolbes-Electrolysis process: Preperation of higher a;kanes by the electrolysis of sodium or potassium salt of lower fatty acids is called Kolbes electrolysis reaction.

15.

Kolbe,s Schmith process: This reaction gives the method for fixation of CO2 in the benzene ring.Sodium phenoxide on heating that 120-1400C under 4-7 atm pressure with CO2 gives sodium salicylate which on reaction with dil.HCl gives salicylic acid(2-hydroxy benzoic acid).

16.

Riemer-Tiemann Reaction: The reaction of pheonal with chloroform or carbontetrachloride in the presence of aqueos alkali at 340k followed by hydrolysisof the resulting product gives salicyldehyde and salicylic acid respectively.

17.

Rosenmund Reduction: Reduction of acid chloride (RCOCl)to the corresponding aldehyde with hydrogen using Pd/BaSO4 as catalyst is known as rosenmund reaction.Here Pd/BaSO4 used as negative catalyst and prevent further reduction to alcohol.

18.

Sandmayer Reaction: The convesion of benzene diazonium salt into halogen of cyano derivative of the parent aromatic hydrocarbon by treating it with a mixture containing the corrsponding salt and the acid is called sandmeyer reaction.

19.

Saponification Process: Hydrolysis of esters in the presence of an alkali is known as saponification.In this process sodium salt of fattyacids(commonly called as soaps)are obtained.

20.

Stephen Reaction: Nitriles can be reduced to corresponding imine with stannous chloride in the presence of hydrochloric acid, which on hydrolysis give corresponding aldehyde. This reaction is called Stephen reaction.

21.

Swarts reaction: The synthesis of alkyl fluorides is accomplished by heating an alkyl chloride/ bromide in the presence of a metallic fluoride such as AgF,Hg2F2 etc.

22.

Williamsons synthesis: In williamson synthesis,when an alkoxide or a phenoxide is made to react with an alkyl halide,an ether is obtained.In this method,haloarenes can not be used for the preparation of alkyl-aryl ethers because of the low reactivity of aryl halides.

23.

Wurtz-Fittig Reaction: This reaction is used for obtaining higher alkane from the halogen derivatives by using sodium.

Mechanism in Organic reactions:

1. Hydration of Alkenes:

2. Dehydration of alcohols:

3. Dehydration of alcohols to give Ethers:

4. Reaction of ether with HI

ORGANIC REASONING QUESTIONS (1)Boiling points of amines are lower than those of corresponding alcohols or Carboxylic acid. Ans: In amines, alcohols and carboxylic acids there is a presence of hydrogen bonding. But nitrogen is less electronegative than oxygen, so the intermolecular hydrogen bond which is present in amines are weaker than the corresponding alcohols and carboxylic acids. So boiling points of amines are lower than that of carboxylic acids and alcohols. (2) Phenol is acidic in nature. Ans: C6H5OH C6H5O+ H+ Phenoxide ion Phenoxide ion is more stable due to resonance. So phenol acts as an acid. (3) Alkylamines are stronger bases than arylamines. Ans: In arylamines, the electron cloud on nitrogen will be increased due to the presence of alkyl group(R) (alkyl group is a donating group) R: NH2 Whereas in arylamines , the electron cloud on nitrogen is decreasing due to the presence of benzene ring (benzene is an electron withdrawing group). Therefore alkylamines are stronger bases than arylamines. (4) Electrophilic substitution (Nitration ,or halogenation, or sulphonation) takes place on Benzene when Benzene contains an electronic donating group(--CH3, or --OH, or --NH2, or --OCH3) OR Electrophilic substitution (Nitration ,or halogenation, or sulphonation) takes place on Benzene at Ortho and Para positions only when Benzene contains an electronic donating group(--CH3, or --OH, or --NH2, or --OCH3)

Ans: Due to the presence of an electron donating group on benzene ,the electron cloud increases at ortho and para positions. So electrophile will attack readily at ortho and para positions. (5) Electrophilic substitution on benzene takes place at meta position when an electronic withdrawing is present (--CHO, --COOH, --NO2). Ans: Due to the presence of an electron withdrawing group on benzene, from the resonance structures, the ortho and para positions contains positive charge cloud so the electrophile can not attack at ortho and para positions so it has to attack at only meta position, having electron cloud . (6) Haloalkanes are more reactive than haloarenes. Ans: In Haloarenes the halogen which is present on benzene ring donates its lone pair of electrons to benzene ring which results in resonance. So resonance leads stability and less reactive. Whereas in haloarenes no resonance results less stable more reactive. (7) Ketones are less reactive towards nucleophilic addition reactions than aldehydes. Why? Ans: Nucleophilic addititon rections takes place when a nucleophile will add to a positively charged carbon. In ketones RCOR, the partial positive charge which is present on carbon is neutralised by two alkyl groups which are electron donating groups whereas In aldehydes RCHO, the partial positive charge which is present on carbon is partially neutralized by only one alkyl group. So ketones are less reactive than aldehydes towards nucleophilic addition. 8. Compare the acidic strengths of Cl-CH2COOH , F-CH2COOH, I-CH2COOH. Ans: F-CH2COOH > Cl-CH2COOH > I-CH2COOH Fluorine is more electronegative than Cl and inturn Cl is more electronegative than iodine. In F-CH2COOH, F is more electronegative and electron withdrawing , so H+ releases very readily and become strong acid than the other compounds. 9. Compare the basic strengths of the following. CH3NH2, NH3, C6H5NH2 Ans: The basic strengths CH3NH2 > NH3 > C6H5NH2 In CH3NH2, CH3 is a donating group, so the electron cloud on nitrogen increases. CH3 :NH2 . In :NH3 nitrogen contain its own lone pair of electrons. In C6H5NH2 , C6H5 is an electron withdrawing group, so electron cloud on nitrogen decreases. So basic strength decreases. 10. Formaldehyde gives cannizaros reaction whereas acetaldehyde does not. Ans: Formaldehyde does not contain -hydrogen, the compounds which does not contain hydrogen undergoes cannizaros reaction. Acetaldehyde does contain -hydrogen, so it does not undergo cannizaros reaction but it undergoes aldol condensation.

11.Phenyl methyl ether (anisole)(aryl alkyl ethers) reacts with HI to give Phenol & Methyl Iodide but not Iodo benzene and Methyl alcohol. Ans: HI is a strong acid , which will cleave the oxygen and alkyl bond, because the Oxygen and Phenyl bond is low reactive. 12. Unlike Phenols, alcohols are easily protanated. Ans: In phenol, the electron pair present on the oxygen is taken by the benzene ring for the resonance. So, electron cloud decreases on the oxygen atom of phenol, so protanation is not easy in the case of phenol. Whereas in the case of alcohol, R is an electronic donating group, so the electron cloud on oxygen increases .So the protanation occurs easily in the case of alcohol. 13. Carboxilic acids do not give the characteristic reactions of carbonyl group. Ans: In carboxilic acids the caboxilate ion is resonancely stabilized. i.e the pi electrons are not localised but they are delocalised between two oxygen atoms of carboxilate ion as shown below.

14. Why is it difficult to prepare pure amines by ammonolysis of alkyl halides? Ans: Ammonia can react with the alkyl halides to form a mixture of primary, secondary, tertiary amines but not pure amines. 15. How aniline is differetiated from N-methyl aniline by carbylamine test? Ans: Aniline is primary amine and N-methyl aniline is secondary amine. Primary amines gives carbylamine test to give isocynides whereas secondary amines does not respond for the carbylamine test. 16.Chloroacetic acid is having higher Ka value than acetic acid. Ans: Any electron withdrawing group on carboxilic acid increases the acidic strength. In chloro acetic acid chlorine is the withdrawing group and also electronegative element. 17.Control of pH during addition of Ammonia derivatives to Aldehydes and ketones. Ans: If the medium is too acidic (low pH value), the ammonia derivatives being basic in nature will form their respective salts. If the medium is low acidic (pH value is high), then the protonation of the carbonyl group of aldehyde or ketone will not occur. This in turn will not increase the electron deficiency (or + charge) on the carbonyl atom of the carbonyl group and hence weak nucleophiles like Ammonia derivatives will not able to reactive. So pH must be maintained at 3.5. 18. Why benzamide is less easily hydrolysed than methyl benzoate. Ans: Nitrogen N is less electronegative than Oxygen O , therefore N can donate its pair of electrons more readily than O. As a result, the magnitude of + ve charge on the carbonyl group of benzamide is much less than that on the carbonyl carbon of methyl benzoate. Consequently during hydrolysis, the OH ion will attack the carbonyl carbon of methyl benzoate more readily than the carbonyl carbon of benzamide.

Conversions:

JAWAHAR NAVODAYA VIDYALAYA, NIZAMSAGAR. Organic chemistry Date: 13-12-2010 Class: XII Max. Marks: 70 I. Distinguish between the following pairs of compounds by giving a chemical test.(Any 10).10M 1) C2H5NH2 and C2H5NHC2H5 3) Phenol and Benzoic acid benzoate 7) Pentan-2-one and Pentan-3-one 9) 2-Methyl -2- Propanol & 2- Propanol 11)) Acetic acid & Acetaldehyde 13) Methanol & Ethanol 8) Aniline and Enthanol 10) Phenol & Anisole 12) Acetone & Acetaldehyde. 14) Phenol & Benzyl alcohol 2) Acetophenone and Benzophenone 4) Ethanal and Propanal 6) Benzoic acid and Ethyl

5) Acetaldehyde and Benzophenone

II. Explain the following named reactions. (Any 7) 1) Wurtz-Fittig reaction. 3) Cannizaros reaction 6) Friedel Crafts alkylation 8) Clemenson reduction. 10) Hell-Volhard-Zelinsky reaction 12) Carbyl amine reaction 14) Hoffman broamide reaction 2) Gattermann reaction. 5) Williamsons Synthesis 7) Rosenmund reaction 9) Cross Aldol Condensation 11) Coupling reaction 13) Riemer-tiemann reaction

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III. Give the reasons for the following. (Any 13) 1) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethyl cyclohexanone does not.

15M

2) During addition of ammonia derivatives to the carbonyl compounds, PH is to be controlled. 3) Formic acid can give Tollens test. 4) Boiling point of an Aldol is higher than the corresponding alkane. Why? 5) Nitration of phenols gives only ortho and para products. Give reason. 6) Carboxylic acids do not give characteristic reactions of carbonyl group.Why? 7) Aniline cannot be prepared by Gabrial Phthalimide synthesis. 8) Benzoic acid is solid while acetic acid is liquid. 9) There are two NH2 groups in semicarbazide. However, only one is involved in the formation of semicarbazones. . 10) Diazonium salts of aromatic amines are more stable than those of aliphatic amines.

11) Ketones are less reactive towards nucleophiles than aldehydes. 12) Explain the SN2 mechanism with relevant example focusing on inversion of Configuration & steric effect. 13) Explain why is o-NitroPhenol more acidic than o-Methoxyphenol? 14) Phenol is more acidic than cyclo hexanol. 15) In the following pairs of halogen compounds, which would undergo SN2 reaction faster? -- CH2-X, -- CH2-X, CH2=CH-CH2-X

16) Which acid of each pair shown here would you expect to be stronger & give reason? i) CH3COOH CH2-CHF-COOH 17) Boiling point of carboxylic acids is higher than that of alcohols of same molecular mass, though both are having O-H hydrogen bond. 18) Halo alkanes react with KCN to form alkyl cyanides as main product while AgCN forms isocyanides as the chief product. Explain. IV. Write the mechanisms of the following. (Any 2) EtOH-H2O 1) CH3CH2CH2CH2Br + KCN 4M CH3CH2CH2CH2CN & CH2FCOOH, ii) CH2F-CH2-CH2COOH & CH3-

2) Hydration of ethene in presence of dilute acids to give ethanol. 3) The dehydration of Ethyl alcohol in the presence of con. Sulphuric Acid resulted the formation of Ethene. V. Complete the following. (Conversions/ word problems) (5 x 5M) =25M 1) Give the structures of A and B in the following reactions.

(OR) An organic compound A having molecular formula C2H5O2N reacts with With HNO2 and gives C2H4O3N2. On reduction, A gives a compound C with molecular formula C2H7N. C on treatment with HNO2 gives D which give positive Iodoform test. Identify A,B,C and D.Write the corresponding reactions. 2) An organic compound contains 69.77% carbon, 11.63% hydrogen and rest oxygen.The molecular mass of the compound is 86. It does not reduce Tollens reagent but forms an addition compound with sodium

hydrogensulphite and give positive iodoform test. On vigorous oxidation it gives ethanoic and propanoic acid. Write the possible structure of the compound. (OR) A compound A with molecular formula C5H10O gave a positive 2,4-DNP test but a negative Tollens reagent test. It was oxidized to carboxylic acid B with molecular formula C3H6O2 when treated with alkaline KMnO4 under vigorous conditions. Sodium salt of B gave a hydrocarbion C on Kolbes electrolytic reduction. Identify A,B and C and write the chemical equations. 3) How will you bring about the following conversions in not more than two steps? (i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde (iii) Ethyl magnesium chloride toPropan-1-ol. (iv) Methyl magnesium bromide to2-Methylpropan-2-ol. (v) pentan-1-ol using a suitable alkyl halide? (OR) Primary alkylhalide C4H9Br (A) reacted with Alc.KOH to give compound B. Compound B is reacted with KBr to give C, which is an isomer of A. When A is reacted with Sodium metal, it gives compound D, C8H18 that was different from the compound formed when n-Butylbreomide is reacted with Sodium. Identify A,B C and D, and write the chemical equations. 4) Primary alkyl halide C4H9Br(A) reacted with alcoholic KOH to give compound (B). Compound (B) is reacted with HBr to give (C) which is an isomer of (A). When (A) is reacted with sodium metal it gives compound (D), C8H18 which is Different from the compound formed when n-butyl bromide is reacted with sodium. Give the structural formula of (A) and write the equations for all the reactions. (OR) An aromatic compound A having molecular formula C6H6O reacts with Zn dust to give an another aromatic compound with six carbon atoms in its molecule, and this compound reacts with fuming Sulphuric acid to give compound B which is fused reacts with CO2 and forms with NaOH to give compound C. compound C compound D which in turns gives compound E

in acidic medium. Compound E reacts with Acetyl Chloride to give a compound F which is a familiar anti pyretic and analgesic. Deduce the structures of A, B, C, D, E & F.

5) An organic compound (A) with molecular formula C8H8Oforms an orange-red precipitate with 2,4-DNP reagent and gives yellow precipitate on heating with iodine in the presence of sodium hydroxide. It neither reduces Tollens or Fehlings reagent, nor does it decolourise bromine water or Baeyers reagent. On

drastic oxidation with chromic acid, it gives a carboxylic acid (B) having molecular formula C7H6O2. Identify the compounds (A) and (B) and explain the reactions involved. (OR) Identify the reagents A,B,C,D,E &Ffrom the following organic conversion. C6H5NO2 Fe/HCl A (CH3CO)2O B Br2/H2O C H2O/H+ D NaNO2/ HCl F VI. Write the IUPAC names of the following.(Any 5) 1) (OH)CH2(NO2)- CH (Cl) CH2 CH2 COOH 3) CHF2CBrClF 5) (CH3)2C6H4(OC2H5) 7) CH3C(OH)(CH3)OCH2CH3 HBF4 E 6M 2) (CH3)3CCH=ClC6H4I-p

4) ClCH2C CCH2Br 6) (CH3)3C CH2CH2 - O CHCH2CH3 8) C6H5CH2CH2COOCH(CH3)2

Practice Paper(Organic chemistry)

Class: XII

Max. Marks: 70
1M 1M 1M 1M 1M 1M 1M 1M 2M

1. Give one example with equation of Wurtz-Fittig reaction. 2. Boiling point of an Aldol is higher than the corresponding alkane. Why? 3. Nitration of phenols gives only ortho and para products. Give reason. 4. Carboxylic acids do not give characteristic reactions of carbonyl group.Why? 5. Why is Formic acid is more stronger than Acetic acid? 6. Give one example with equation of Gattermann reaction. 7. Aniline is weaker than Cyclohexylamine. Why? 8. Why does Bromination of aniline, even under very mild conditions give 2,3,5tribromoaniline instantaneously. 9. Give one example of each of the following: a) Cannizaros reaction b) Wolff Kishner Reduction 10. Write IUPAC name to the following: CH3 Cl COOH | | Br a) CH3 - CH CH CH2 COOH b) NO2 2M | NO2 OH 11. Write the following (Give equations only): a) Williamsons Synthesis b) Friedel Crafts alkylation OR Write the following (Give equations only): a) Rosenmund reaction b) Clemenson reduction. 12. How will you distinguish between C2H5NH2 and C2H5NHC2H5, based on chemical test. Give equations. 13. Explain the following: a) Phenylamine is more soluble in HCl than in water. b) Aniline cannot be prepared by Gabrial Phthalimide synthesis. 14. Account for the following: a) Benzoic acid is solid while acetic acid is liquid. b) Ketones are less reactive towards nucleophiles than aldehydes. 15. Account for the following observations: a) Oxidation of Toulene to Benzaldehyde with CrO3 is carried out in presence of Acetic anhydride.

2M

2M 2M 2M

b) Melting Point of an acid with even number of Carbon atoms is higher than those of its neighbours with odd number of carbon atoms. 2M 16. Explain why is o-NitroPhenol more acidic than o-Methoxyphenol? 2M 17. Explain why? a) The dipole moment of Chlorobenzene is lower than that of cyclohexylchloride? b) Grignard reagents should be prepared under anhydrous conditions. 2M 18. p-Dichlorobenzene has higher Melting Point and Solubility than those of o- and m- isomers. Discuss. 2M 19. Write the IUPAC name to the following: a) (CH3)3CCH=ClC6H4I-p, b) CHF2CBrClF, c) ClCH2C CCH2Br 3M 20. Write the mechanism of the following reaction: EtOH-H2O CH3CH2CH2CH2Br + KCN CH3CH2CH2CH2CN 3M 21. Decribe the mechanism by which the Hydroxyl group attached to an aromatic ring is more acidic than the Hydroxyl group attached to an alkyl group. How does the presence of nitro group in phenol affect its acidic character? OR Write the mechanism of the reaction of HI with Methoxymethane. 3M 22. Write IUPAC names of the following compounds. a) b) (CH3)4 c) CH3CH2 - O CH( CH3)CH2CH3 3M 23. How do you distinguish Primary, Secondary and Tertiary alcohols. 3M 24. Describe the following: a) Cross Aldol Condensation 2M b) B) Hell-Volhard-Zelinsky reaction 1M 25. Give plausible explanation for each of the following: (i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6trimethylcyclohexanone does not. (ii) There are two NH2 groups in semicarbazide. However, only one is involved in the formation of semicarbazones. (iii) During the preparation of esters from a carboxylic acid and an alcohol in the presence of an acid catalyst, the water or the ester should be removed as soon as it is formed. 3M 26. Give simple chemical tests to distinguish between the following pairs of compounds. a) Acetophenone and Benzophenone b) Phenol and Benzoic acid c) Ethanal and Propanal 3M 27. Write short note on : a) Hoffmanns Bromamide reaction b) Carbylamine reaction c) Coupling reaction 3M 28. Give the structures of A and B in the following reactions.

5M OR An organic compound A having molecular formula C2H5O2N reacts with With HNO2 and gives C2H4O3N2. On reduction, A gives a compound C with molecular formula C2H7N. C on treatment with HNO2 gives D which give positive Iodoform test. Identify A,B,C and D.Write the corresponding reactions. 29. An organic compound contains 69.77% carbon, 11.63% hydrogen and rest oxygen.The molecular mass of the compound is 86. It does not reduce Tollens reagent but forms an addition compound with sodium hydrogensulphite and give positive iodoform test. On vigorous oxidation it gives ethanoic and propanoic acid. Write the possible structure of the compound. 5M OR a) A compound A with molecular formula C5H10O gave a positive 2,4-DNP test but a negative Tollens reagent test. It was oxidized to carboxylic acid B with molecular formula C3H6O2 when treated with alkaline KMnO4 under vigorous conditions. Sodium salt of B gave a hydrocarbion C on Kolbes electrolytic reduction. Identify A,B and C and write the chemical equations. 3M b) How will you bring about the following conversions in not more than two steps? (i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde 2M 30. How are the following conversions carried out? (i) Propene to Propan-2-ol. (ii) Benzyl chloride to Benzyl alcohol. (iii) Ethyl magnesium chloride to Propan-1-ol. (iv) Methyl magnesium bromide to 2-Methylpropan-2-ol. (v) pentan-1-ol using a suitable alkyl halide? 5M OR a) Prymary alkylhalide C4H9Br (A) reacted with Alc.KOH to give compound B. Compound B is reacted with KBr to give C, which is an isomer of A. When A is reacted with Sodium metal, it gives compound D, C8H18 that was different from the compound formed when n-Butylbreomide is reacted with Sodium. Identify A,B Cand D, and write the chemical equations. 3M b) How the following conversions can be carried out? (i) Propene to propan-1-ol (ii) Ethanol to but-1-yne 2M