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Chapter 7

The document discusses the chemistry of alcohols, phenols, and ethers, including their definitions, reactions, and properties. It includes various questions and answers related to the identification and classification of these compounds, as well as their reactions with different reagents. Additionally, it covers methods of distinguishing between primary, secondary, and tertiary alcohols, along with specific reactions such as the Kolbe Schmidt and Reimer-Tiemann reactions.

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41 views9 pages

Chapter 7

The document discusses the chemistry of alcohols, phenols, and ethers, including their definitions, reactions, and properties. It includes various questions and answers related to the identification and classification of these compounds, as well as their reactions with different reagents. Additionally, it covers methods of distinguishing between primary, secondary, and tertiary alcohols, along with specific reactions such as the Kolbe Schmidt and Reimer-Tiemann reactions.

Uploaded by

mrquenic
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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SCIENCE ACADEMY BIAORA, RAJGARH | 2024 UNIT-7 Alcohols, Phenols and Ethers > Marks =6 I > Ale introduction :- Alcohol and phenol are the derivative of hydrocarbon, They are formed by os replacement of hydrogen of aliphatic and ydrocat pyaar ee ee ee a Alkane ~+OH~ Alcohol ArH i Ar-OH Et bem agus ; Phenol 4, her :- Bthers are formes the replace! y ot by rae enett of hydrogen atom of aban By) ‘oxy (RO). ‘Alkane 40H Ether yY sctit e stions — 1. Which of the compound is Aspirin ~ y (i) Acetyl salicylic acid (ji)Salicylic acid _(ii)Ae = (iv)Salicyl amide 2, Which is used for poisoning the alcohol- mae y Methyl alcohol (ii) Ethyl Alcohol (il) Glygerige- (iv) All the above 3, Which is identified by Lucas reagent — Vay % (ivAlconol hd zs (i) Phenol (ii)Ether —(iii)Aldehyde 4, Carbolic acid is — @ Phenol) (ii) Phenyl benzoate (i 5, Lucas reagent is i 1804, (ii)ghydrous ZnCle (iv) Cones HCl and anhydrous ZnClz () Con, HC! (ii) Cone. 6. Which compound is known as ol ofiyinter B21 = acetate (iv) Salol i (i) Phenyl benzoate _(i),phenyl saliviate (Gi) pheny! 7, Alcohol react with Na 0. form - 5 (ROR (i) RONa (iii) RL (iv)RCHO 8, Reaction for the formation Of salicylaldehyde from phenol is- (i) Rosenmund seaction (if) Friedel Crafts reaction (ii) Reimer-Tiem: (iv) Wurtz’ eaction « 9. Used aganannestietic= |. : () CHO “(ji CHsOH (iti) CHsCHO (iy) (Calf920 10, Gives Libermann’s nitroso (7 : ne “ a OH i) CaFls Oe Cte a densed with - ann reaction: i) ¢ 20, formed when phenol is cone 5 CHO (i) CHCHO (ii) CotlsCHO (jv) CHCOCHS Fill in the blanks :- ' i ) formula of alcohol is Cc faa ether is Call0t20- 2, General formula 0} BHUPENDRA YADAV ~ 62. 99777130098 024 SCIENCE ACADEMY BIAORA, RAIGARH]? x er used as an ansstbeti: 4 On heating formaldehyde with phenol Bakelite i formed 5 Phenol eats with phthalic acid give acid-base indesor 6 Chlerotoraris formed on heating ethyl sleaba wth bleach Mai rad of Kote Sci rein of pts Alcohol is Neutral whereas phenols of aid 9. Ones aol wth cone SO, for 170 alkene oe 10. Edy aleobot ar ethanol i called spPyt of wine. 3 pr 11. Oxidation of pity eleabol gives aldehyde 12. Oxidation of sccondary alcoho gives Ketone. 13, Metyalohol salle 14, Alcohol bare high olin points de to he pesece of hydrogen 1S, Reaction of nitrous acid on a primary amine te form 8 16, Bemzene is formed on heating phenol with Zn powdet. 17, Alcohols are soluble in wate, Its main reason i. 18, Williamson's Synthesis is used inthe manufacture of 19. The dipole moment of ether i less than that of aeobol. 20, Phenol reacts with soumonia to form aniline, 21. Pure alcohol is 100% ethanol 22. Isopropyl benzene is called Cumene. 2. The process of show decomposition of com fermentation, 24, Anisole reacts with a mixture of nitro anisole and p-nitro anisole, 25.24,6 Trnitrophenolis called 26, The structure of glycerol is ¢ 61 1g powder. 2 a flex byztite compounds by enzymes is called enleated 260, and Con, HNO, to give a mixture of o- @3) ; 4) th andi IUPAC names propa, 27. The mode of dehydrajG gf alas is 3° alcohol >2°aleohol> alcoho. 8. Formaldehyde rea jenard reagent fo form primary alcohol. lee :- ‘Answer in one wot meh Phenol reacts with chloroform and sodium hydroxide (NaOH) to form 4. Mie esis obtained daring fermentation? » ‘5. Nami the primary aleohol which gives iodoform Ethanol (CHs0H) : oe 6, Naine the reaction ia which phenol reacts with chlorofori and sodi BHUPENDRA YADAV - 9977730098 ium hydroxide(NaOH) to form 6. SCIENCE ACADEMY BIAORA, RAJGARH | 2024 salicylaldehyde. Reimer-Tienann reaction 7 In vitor meyer method, 1 aleobol gives which colour with base Red 8, Anaesthetic agent is — her (R-O-R) Q.1 Differentiate primary, secondary and tertiary alcohol by oxidation and de} dons method « ay ‘Ans, 1, Oxidation « aldehydes rand equal to that ‘CHyCH;OH)__, cH,cHO_!_, cH,CooH Ethytaleohol "2° Acetaldehyde ‘Acetic acid Secondary alcohols Secondary aleohels on oxidation eh Shietisiay selene. Kno onan y egg che ome fain vik umber or earbon atoms i less than hatin the orig gl CHy-cH.OB, J,” cH,e=0_ 8 WPesieaox Co, + 20 GY “0? cial inag Propan-2-0l Acetone: Nagiiewia ‘Tertiary aleohols :- Tertiary alcoholyéré oxigized with difielty as compared to primary and Secondary alcohols, By the oxidation by strong oxidizing agent (HNOs, KyCr.07) first ketone and the ai coining leser umber fo om han cool ore Chis CHy- C- OH HC = CH, Hl, CH,-C=0 + CO, +H,0 Hy we Roi CH, ‘Tentary butyl aleaho cetone Tigo} vcscoon al “ Acetic acid 2, Dehvarogt Sia sen vapour of alcohol is passed over heated Cu at 300 °C. than hydrogen atom js set jong with the hydrogen atom of OH group, This proces is called Dehydrogenatons. 18 algoHobon dehydrogenation gives aldehyde, “yCHCHOH ——, CH,CHO + Hh “Ethyl alcohol °° Acetaldehyde 2° alcohol on dehydrogenation gives ketone. CHyCH-OH 2, CHC=0 + Hh CH (ke Ci Eu IPENDRA YADAV - 9977730098 SCIENCE ACADEMY BIAORA, RA Propan-2-ot Aston aleto give alkenes 4) alcoho are not dl drogennted but lye a water molec #8 ott Cli,E= CH +120 bee ee 2emethyl prop-1-e on leohols. Qa Explain dehydration in primary, secondary and tertiary al : “has. Denydration = When alcohol is heated with concentrated H,SOs, a moet fnyrogen atom is released along with the OH group. Other major dy gett RBG #7° HIPOg P:0s, AhOs, KHSO, and ThO; ete. Primary alcohol - On heating primary aleohol to high temperat Ryne of dehydrating agent like con, H,S0, alkene is formed. CH;CH,OH 7 CH=CH + Ethanol "2% “Ethene Secondary and Tertiary aleohols undergo dehydrating shedmmptratvely low temperature, Secondary alcohol CH;-CH-OH 0? ae 1H, +H;0 CH, Isopropyl alcohol Tertiary alcohol CH; Y ws)” CHs-C=CH, +10 & Hee Teatiary Butyl al ‘The sequence of dehydratifn of different alcohols is as follows. 3° alcobdh AQ? pleohol > 1° alcohol 9-8 Explain the toes of debydration of aeoho. 09) fm. Deir irati : a ae is heal with concentrated H,SO, , a molecule of water is iol to form an alkene, This reaction is call tio i Behy ahi: j8 released along with the OH group, ee CH;CH,OH _l Bet released fom te alcohol to form an alkene, This reaction is called dehy draeQee™ In this a (CH= CH + 1,0 Med or penvération Nesta 7 ie a \ehydration :- Mechsnism of dehydration of alcohol involves the following steps~ tion of protonated alcohol (Oxonium salt) ~ One mole of aleoh ‘rotoh to form oxonium salt. This step is reversible, ae Fast iH CH;—CH,-O-H +Ht === CH,-cH,-0-H Protonated dleoho! (Oxonium aleoho!) BHUPENDRA YADAV -9977730098 65, Gi) Formation of Carbocation mainly dehydrating. Ttinvolves SCIENCE ACADEMY BIAORA, RAJGARH | 2024 slo which ithe ate determining step and this step is of water and formation of carbocation. H + CH= CH;-O-H ep CH=CH + 10 é carbocation Gp Formation of Ethene ='This carbocation ely eliminates proton by HSO, by which el Q.4 What is Lucas reagent ? How are primary, secondary and tert SBF by it Explain. CO (3,1) ‘Ans, Lueas reagent :- Lucas reagent isa solution of anhydrous Z, solution is used to classify alcohols of low molecular weight. (On adding the alcohol to Lucas reagent, a tertiary alcohol re presipitat(PP1) of alkyl chloride, IF the precipitate appears Secondary, [fno precipitate is obtained in cold, the alogitisp ‘Tertiary aleohol CH eS oe) CHy-C-OH)+ Cons HCI)“ NCCI + HO Ci CH (Immediately vy Secondary alcohol CHy-CH-OH + com HCR #820 CHy-CH-Cl + HO chy CH (after five mit Primary alcohol CHy-CHr-OBS Meo Hicl “YS 20, No reaction (No turbidity s produced) Q5-Write Vj PSS units Ans. Vie feys? method : The test completed in the following steps- (i The elvelfgloohol is first converted tothe alkyl iodide by reaction with concentrated HI. is treated with silver nitrite (AgNO;) to form nitroalkane. ei finally treated with nitrous acid (HONO) and made alkaline with NaOH, —+ Jfa blood red colour is obtained, the original alcohol is primary. —+'If' blue colour is obtained, the alcohol is secondary. —+ If no colour is produced, the alecko is tertiary, CH=CH, +HSO, ep CH= CH, + H,S0, Ethene ‘This way, acd used in the firs step () i released instep (Il). ‘method to distinguish primary, secondary and tertiary alcohol, Primary alcohol BHUPENDRA YADAV -9977730098 66. See SCIENCE ACADEMY BIAORA, RAJGARH | 2024 3, __| Litmus test Turn blue litmus red. Does not affect litmus paper 4, _ | Ferric chloride ‘On treating with neutral FeCl; ‘Alcohol does not give any . test solution phenol gives red to violet colour. ve ee 3, | Reaction with ‘No reaction. Ethyl hailde is obtained. halogen acids : ral 6. Bromine water | Phenol gives light yellow Alcohol does not ‘omipe test precipitate of its bromo water test. derivative. 7, |Todoformtest | Phenol docs not give idoform | It gives ae form yellow test. ppt) \ Q.8 Compare Ethyl aleohol and Diethyl ether. QR 4 Ans. SINo. Test Ethylaleohol__g \_ Diethyl ether 1 | Physical test Volatile liquid high BP. Geos] Volatile liquid low B.P. due H-bond. to absence of H-bond. No reaction 2 | Reaction with Hydrogen gas is fo) sodium 3 | Reaction with PCI; | Ethyl chlorid Ethyl chloride is formed when reacts with Cold POIs, itreacts with PCls on heating. | 7 __|Reaction with air_| No reaction, Forms peroxide. 5___ [Solubility in water_| Soluble inyvater. Immiscible in water. Q. 9 Explain the following reactions: y i) Kolbe Schmidt reaction (09) \iipReimer-Tiemann reaction (09,16,17,24) (iil) Coupling reaction (09,24) Ans, (i) Kolbe Schmidt régcfion :- When sodium salt of a phenol is heated with CO at 130°C. and 4-7 atm pressure, $0 is formed. his on acidification gives salicylic acid, This reaction is called Kolbe Schmidt reaction, Nan & OH oH O bre oo si oO coon wo E> ae cA Sodium salicylate Salicylic acid or o-hydroxy benzoic acid (i) ReimerJTi es reaction :- When phenol is treated with chloroform and aqueous sodium ( 0 C, o-hydroxy benzaldehyde and p-hydroxy benzaldehyde are formed. The orthojsémer is the major product. This reaction is called Reimer-Tiemann reaction. OH OH CHO + CHCI, + 3NaOH ——> + 3NaCl + 21,0 phénol chloroform o-hydroxy benzaldehyde or Salicylaldehyde BHUPENDRA YADAV — 9977730098 68. SCIENCE ACADEMY BIAORA, RAJGARH | 7024 iene pr nl sweated with zoom chloe inde presence of Wiping retold Coin @:xOyoH + Hel prhydroxyazobenzene (Gi) Coupling reaction ‘-hydroxyazobenzene are ©xa+ Opou phenol Benzene diazonium chloride (Q-4WEletrophilic Substitution Reaction (ESR) "Wie the equation of following reactions of Phenol. ‘ (@Hslogenation — ()Nitation (Gi) Sulphonation _ (jv) Allylajon\\ ¥a}Acylation (Gi) React with Zn dust (vil) React with Ammonia (vii) React witht anby ride How cin you obtsined following compounds trom pheio: (.24.6-Tribromophenol (i) 2,46-Tenitrophenol Pirie acid (ii) o-bydroxybenzene sulphonic (iv) o¥fesol, p-cresol (w) echydroxy acetophenone, p-bydroxy aoetophenone (i) Benzene i il) Phenolphthalene (vi) Aniline Ans-(i) Halogenation :- Phenol is react with broming. bromophenol and p-bromophenol, OH 0 orAVO . ih hy Br OH ‘p-bromophenol sence of CS; ot CHC! to from o- 2HBr 3 + 28, ——+ < Phenols orbs o 2,46-Tribromophenol Phenols is e. bromine water to from white presptate of 2,46- feel H <> "oO £5 TT «ine OH + 10 "Br 24,6-trbromophenol ct with dilute nitric acid (FINOS) at low temperature to form o- Cee ones mage, ¢ (ii) Nitration ;- Phi 21,0 ‘oN ophenol NO, . . ne pet ophenol 2,4,6-Tyinitrophenol (Picric acid) ; Pheaol is reacts with concentrated HNO, and Concentrated H,S0j solution to form 2,4,6 Trinitrophenol or picrie acid, OH OH oO NO: yy NO; + HINO; iso, + 3140 NO: 2,4,6 Trinitrophenol or por BHUPENDRA YADAV - 997730098 6, SCIENCE ACADEMY BIAORA, RAJGARH | 2024 sybenzene sulphonic acid iy Swhohonaton Phenol is reaet with one $0, form o-ydrox i Sydroxybenzenc sulphonic acid OH OH OH SO + HSOEe + “Iho SOs ‘o-hydroxybenzene _priydroxybenzene CChlorobenzene sulphonic acid sulphonic acid (jv) Alktation + AS -cresol, p-eresol :- Phenol react with methyl chloride in the presence gia Hy toe ‘o-eresol and p-eresol are obtained. a oe 3G Na best amu Oy + CHCl anhydrous Al + + CH o-ctesol ie (eta yson, pony acetopenmne Cp aalar acetophenone, p-bydroxyactopheno Phehol react with acetyl chloride inthe presence of +e ICI, to ftom o-hydroxy reatphenone and phony acelophenone oH Ae) (oH Gin naan QP? Qo, sexy loi & . piygiony * yphenone ‘acetophenone vi) React wth Za dust = ve ee cas ‘powder to form Benzene, anhydrous ZnCl at high temperatare ted with ammonia inthe presence of fromtie primary amine( Aniline). OH 6 + Nth aiysou ch, O) + 120 ~ 9 Kailine ii React with Phthalic anhydride 5 pt Ce pthaene: Two molecule of Phono react wih pts anhytrid in he presen ae ESO, om phenolpilen. which an fr sid base indesor and is used as. medicine é BHUPENDRA YADAV - 9977730098 2024 SCIENCE ACADEMY BIAORA, RAJGARH oH oH gu gH 0} g g Con. HSQ¢ 9 q + Q ~H0 i as ° Qo» § ¢ 6 8 phenolpthaein Oo .Q/11 Give chemical equation of the folowing conversion. () Ethylene from ethanol (ethyl alcohol. Diethyl ether from ethanol(ethy! alcohol), Ethanol(thylaleohol) from diethylether, (jv) Etly] acetate from ethanol(ethyl alcohol), { ( (») Ethanol(cthyl alcohol) from glucose, ss (0 Ethylene from ethanol ethyl alcoho) :-Etyhgled Myon heating a 170°C with concentrated H:S0,, onc molecule of water is rel alcohol and ethylene is formed CHCH-OH HO, CH= CH NEED) at Ethanol = TB {0 eth eer from ethanol (thy sleahot) \Ophcatng ey aleotol in excess wih “onesninte’H:SOe one molecule of HO Rata aad dey ther is formed, GHsOH +1480, WA WHF Hs0, + 1,0 4 ES GHETSO, + Hy CHS HSO, + Cation AES GHin0.CHt + 1450, . ethyl ether = (ii) Ethanol(ethyl alcohol) from are eth When ether is heated with dilute H,$O, in the Presence of press, th isn esha ZHs-0-CHae EO jabltiso, 2C41, OH dit tg So Ken (Ey ace rete ath is tated with act 5 cohol): When ety! sleohol is treated with thepesins o LST a Ss ee a Gee OOH so, Ciscoe sito Ethyl acetate BHUPENDRA YADAV ~ 57773009 n, SCIENCE ACADEMy BIAORA, RAJGARH | 2024 Deller Prepared inthe ly erfication PrOCCSS by the heating 4 . setts ms y the heating ethy| alcohol ‘ith concentrated sulphuric acid at 140 °C. The real ratory and, ‘industry by the Williamson continuous provceds in Wo stege Gl we HIOH + uhiso, — TL. caso, + 0 [HS0, + Fy convert an exces of alohol into ether. So, this method w elon Williamson conti iyiatet CHHIESONS Hoos, wee, Cth.0 cs + Hs0 a a iethy] ether suiphuric acid is regenerated in the reaction hence, it appears that only a small ay (@) Water formed in the Teaction dilutes the acid and its reactivity (B)_Apart of sulphutio acids reduced by alcoho into sulphur dg 1 Deserbe the laboratory method of preparation of det! ty er thus obtained is prified ? (01,03,05,06,09,10) fins. Laboratory method of pre i tion of Diethyl ether | ether is prepared in the inportory and industry by the Williamson continuous etheretion process bythe heating ey ol wth concentrated sulphur ald at140 aaa CaulOH HSO, ie Tho eds in two steps, ethyl aleohol CH;[HSO, + HOCH, rocedur®.- Sehsitol (2 volumes) and concentrated sulphuric acid (1 volume) are taken ina Enis iye aed afta 413 K, Ethanol is added at the same rate at which ether 7 is collected in arecei in ice-cold water, digit jad is collected in a receiver cooled in oe-co ee Puri : Ether contain ethanol, water and sulphuric acid as impuri Srp nip a ees agitated with 50% solution of calcium chloride o remove alcohol, ae , 9 a tis then washed with water, dried over anhydrous calcium chloride and redistilled, Q.14Pure phenol is a colourless solid but why it is converted into pink after some tim ~ 011,18), BHUPENDRA YADAY ~9977730098 a SCIENCE ACADEMY BIAORA, RAJGARH | 2024 SCIENCE ACADEMY BIAORA, RAJGARH [2024 2CH,OH + 2Na—_,. -xplain with react ‘Or What change in colour is observed in phenol in presence of oxygen? Exp kr ‘Ans, When phenol is lef pen in air and ligt, it slowly gets oxized and tus pink. At fis ‘quiaooe is forme which gives an addition reaston with phenol to form a deep pink colour Substance, which is called phenoguinone ° ox 6 eo en) eee © Serene In pheaoguinoas, two molecules of phenol are linked with one molecule tain a anaes et ty pote ~ 20. on @ow a @y Pacoquinaae at coer) 3 esata at et = @) What is the reaction of diethyl ether wis 2C4HLONa + 1, (16 How are the following com GQ Propene -—» Propandta (i) Benzyl chloride —, Benzyl alcohol oF (i) Etylmagnesium chloride ——© Propan-t-ol oy (is) Mebiyl magnesium bromides 3 methylpropan--a Ans. () CH;CH= CH, + Con.H,S0, —» + mo +. “ACY 80, axe mony NS : * Qnton =. 0" 35,48 versions carried ont: Benzyl elloride Benzyl aleohol (Gi) Alkyl halide reacts with sodium alkoxide, (i) CHLCHMECI + HERO one, CHC oe Gv) Phenol heated with Zn powder. (23) (9) Ethyl aleobol is treated with B;S0, at 4 (a3) Ethyimagnesium chloride LOH+ Me(OE)C. - (i reaction ofpheaol with sodiam. | ( ae ‘Ans. (2) Pheals are prepared by hydroly jum salts by water, dl. Acids ets, & ol b b NCI a (iv) CH)MgBr + CH;-C-O —+ GJ ok 4. HO ——> sae , ‘Methyl magnesium ‘2-methylpropan-2-01 ee acenia Vere ane (i) The reaction of Difthyl elief with conc. HI acid, on heating gives one molecule of ethyl iodide cohol. FH __ 100% © GiHpOH + CH sci and lsh bag aeeet? (115) ee Oral phen th contin “OH grou, What the reson that pena aie re? Maer acids as compared to alcohols is that phenols cxistas a resonance hybrid. samen bh LE [B © Pa 6 ©. & rome & QUT Ethyl alcohol and; re contain -OH group. What is the reason that phenol is Ethanol Ethyl iod ge thy oxygen atom gets a postive charge and attracts the electron pair ofthe O-H_ by reacting ally halide wit sodium alkoxide, fides the release ofa proton. The phenoxide fon formed after the release ofa fe0CH——* —CHOCH; + NaCl lied by resonance. CqHOH == CiHO" + HT « cs obtsined by heating phenol with Za powder Phenoxid on OH + Zn——> Clg + Zn0 od to the oxygen that’s 11 Seofols, no resonance is possible hence the hydrogen atom is strong! why Phenol i acidic and sleoho s neutral (0) Ethers obtained by testing ethyl alcohol with 1,0, et 413 K. i CREE CHO GH OCH HHO: Q. 18 Give two reactions that show the acidic nature of phenol. Compare its acidity with that of ethanol. ‘Ans, The reaction showing acidic character of phenol are ~ (vi) Phenol reacts with sodium, sodium phenoxie is formed and hydrogen gas is liberated. BHUPENDRA YADAV -9977730098 1, F BHUPENDRA YADAV ~9977730098, B. f intremeremere sx » SCIENCE ACADEMY BIAORA, RAJGARH|2024 ‘Reaction with sodium - Phenol reacts with sodium to give Hs BAS. OH (©) Reaction with NaOH ~ Phenol disolve in NaOH to give sodium phenoxide OH Na sodium phenoxide ‘han ethanol, This is duc to the phenoxide fon let fein ‘fom phcnal is subiizedby resonance while eho eleanor Q.19 Writea notes on fermentation, ‘Ans.The process of slow decompos SPinbounds in the presence of enzyme eatalyst is called fe living substance. The enzymes present i invertase ete, ‘When yea is mixed in glucose solution and kept result of fermentation, CHO, ase, 20 i point than that of hydrocarbon, but © She molecular masses, but: Point besause propanol in polar fs presen eto wih a ‘Donding between its molecules: Nene ‘hydrogen bonding is n¢ ofthe polar OH pou your as Js Ng Mtl ot polar in sae, When nol dod inweter, ena mht breaking thong eyeing tae ee Boye ine RDB Ornadlo,, 1 Hest Higa h On te ote hand, bydroctbons are non pole roleules and be BHUPENDRA YADAY —9977730098 ox 6 +140 iS) Pezala mor sid ofa photon tame? propanol has a higher boiling ong inermolecolae hydrogen ot present due tothe absence

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