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    wohabia bet ate 7) LL AY NCERT : MUST TO NUGCURAAINES: BY OM PRABHU A =) PSB al RAHENGE YE WADA HN HAMARA GURENTEED WW! AT 24 DAY 6 TARGET CHAPTER WITH TOPICS TO) Haloalkanevand Haloarenes i e Introduction, Classification IUPAC ¢ Methods of preparation of Haloalkanes and Haloarenes ©) 7 Nessl ela iane clalel =idelele e Introduction, Classification, IUPAC e Structure of Functional Groups ¢ Methods of preparation of Alcohol SELECTION LEKE RAHENGE YE WADA HN HAMARA vaner studying this Unit, You will be er si able 10 ‘same alcohols, phenols and Miners according to the IUPAC gystem of nomenclature; discuss the reactions involved in the preparation of alcohols from ‘alkenes, aldehydes, ketones and carboxylic acids; discuss the reactions involved in the preparation of phenols from haloarenes, benzene sulphonic acids, diazonium salts and cumene; * discuss the reactions for preparation of ethers from {i) alcohols and (i) alkyl halides and sodium alkoxides /aryloxides; correlate physical properties of alcohols, phenols and ethers with their structures; * discuss chemical reactions of the three classes of compounds on the basis of their functional Bey ‘ yar at aa! v UN > RA? sey ROW gotaracd Ker ont F Phun PO dou Hoss TQ Peuapnonad ery os \\ol(Papers, currency notes, cheques, certificates, etc. The —S BY ware ) Aunts DELHI Ssxaeanvbl) be (0) Clonal fesasm cusnond— Alcohols; Phenols and) Ethers Alcohols, phenols and ethers Gre the baste compounds for th formation of de 2 pounds for the Hergents, antiseptics and fragrances, respectively and applications. Aleohols and phenols are formed when a hydrogen atom in a hydrocarbon, aliphatic and aromatic respectively, is replaced by -OH group. These classes of compounds find wide applications in industry as well as in day-to-day life. For instance, have you ever noticed that ordinary spirit used for polishing wooden furniture is chiefly a compound containing hydroxyl group, ethanol. The sugar we eat, the cotton used for fabrics, the paper we use for writing, are all made up of compounds containing -OH groups. Just think of life without paper; no note-books, books, news- magazines carrying beautiful photographs and interesting stories would disappear from our life. It would have been really a different world. An alcohol contains one or more hydroxyl (OH) \group(s) directly attached to carbon atoms), of an aliphatic system (CH,OH) while a phenol contains -OH group(s) directly attached to carbon atom(s) of an aromatic system (CjH,OH). The substitution of a hydrogen atom in a hydrocarbon by an alkoxy or aryloxy group (R-O/Ar-O) yields another class of compounds known as ‘ethers’, for example, CH,OCH, (dimethyl ether). You may also visualise ethers as compounds formed ® wot CAEP SS c & . POT) substituting the hydrogen atom of hydroxy! rouP F(a ales | \ eS i group. . K peer an sy the chemistry of three classe,, SS hall diseu! Boa ene phenols and ethers. © ota compounds, namely — alcohols, akes their study systematic a i] i ds mi: 111 Classification ‘The classification of compounds Makes TT are alcohols. phen, tence simpler. Therefore, let us first and ethers classified? fied as mono-, di-, tri- | 11.1.1 Aleohols—\ Alcohols and phenols may be classi } Mono, Solyhydric compounds depending on whether they contain one, ty ace three or many hydroxyl groups respectively in their structures ; | QyGe\vounrfeeh sven betow: pes alcohols—“! CH,OH fe na CHOH a) (rol T S wget C,H,OH CH,OH Monohydrie Dihydric ‘Trihydric RYOHO Monohydric alcohols may be further classified according to t hybridisation of the carbon atom to which the hydroxyl group ( C me attached. \ 3) concageT ing C,.—OH bond: In this class of alcohol coe (@ Compounds containing bond: In is SS 101 the -OH group is attached to an ‘sp’ hybridised carbon atom of: Re @® wdhangoD alkyl group. They are further classified as follows: estos Primary, secondary and tertiary alcohols: In these three types alcohols, the -OH group is attached to primary, secondary a i tertiary carbon atom, respectively as depicted below: —cH;-oH >cH—-on >c-on Primary (1°) ‘ Secondary (2°) Tertiary (3°) Allylic alcohols: In these alcohols, the —OH group is attached! a sp’ hybridised carbon adjacent to the carbon-carbon doub! bond, that is to an allylic carbon. For example 8 a CHjsCH-CH-OH — CH,=CH-C-OH CH,=CH-C-OH 6 Be Paar Secondary pokey lic alcohols: In these alcohols, the —OH group is al tach® to a sp’—hybridised ‘ ci ‘hyl ‘ed carbon atom next to an aromatic ring Chemistry 324 ts youtube:com @OM_PRABHU_AlIMS_DELH 4 ‘tps: melemprabhuaimed —OH -o-0=m oo ‘ Primary Secondary Tertiary Allylic and benzylic alcohols may be primary, secondary or tertiary. (i Compounds containing C,»-OH bond: These alcohols contain —OH group bonded to a carbon-carbon double bond, ie., to a vinylic carbon or to an aryl carbon. These alcohols are also known as vinylic alcohols. Vinylic alcohol: CH, = CH - OH OH .1.2 Phenols— BE Mono, Di iN ou egy nth and CH, trihydric O Cy Cy OH phenols OH Monohydric — Monohydric Dihydric Trihydric 11.1.3 Ethers Ethers are classified as simple or symmetrical, if the alkyl or ary! groups attached to the oxygen atom are the same, and mixed or unsymmetrical, if the two groups are different. Diethyl ether. C,H;0C3H,, is a symmetrical ether whereas C,H,OCH, and C,H,OC,H, are unsymmetrical ethers. Intext Questio 11.1 Classify the following as primary, secondary and tertiary alcohols: CHy 1 @ CH,- C — CH,OH (i) H,C=CH-CH,OH H Cs On CH-CH, (iii) CH,- CH- CH,-OH liv) CH, CH=CH-C-OH -CH-Cl “Orne «On 41.2 Identify allylic alcohols in the above examples. Ho Vomanclatise (e@) Alcohols: The common name of an alcohol is derived from the Ae Nomenclature i ; common name of the alkyl group and adding the word alcoho! to it. For example, CH,OH is methyl alcohol. (825, Alcohols, Phenols and a ee amas Intpsit-meomprabhuaimsd Smee s 9, Class XI), the name of an g namin cote eh a iS ‘gubstituting ‘eof alkane with the suffix Siete Positis, substituents are indicated by numerals. For this, the longest ca, g at the end nearest i, and other substit,, chain (parent chain) is . The positio s De aetst by taing the vumbers of carbon atoms fe pti thes attached. For naming po! ols, the ‘e’ of alkane is ret and the ending ‘ol’ is ‘added. The number of -OH groupes indicate, adding the multiplicative prefix, di, tri, etc., before ‘ol’ a he Posi OH groups are indicated by appropriate locants, eg, L-Ch,. is named as/ethane-1, 2-diol. Table 11.1 gives common and Il; names of a few alcohols as examples. TUPAC Names Table 11.1: Common and of Some Alcohol eee HT Frome Methanol Propan-1-ol Propan-2-ol Methyl alcohol r-Propy! alcohol Isopropyl alcohol OH (CH, - CH, - CH;- CH,~ OH CH,- CH - CH,- CH, ou CH, - CH CH,-OH CH, CH, go Butan-1-ol Butan-2-ol n-Butyl alcohol sec-Butyl alcohol Isobutyl alcohol | 2-Methylpropan-l1 tert-Butyl alcohol | 2-Methylpropan-2 CH, HO-H,C-CH,-OH Ethylene glycol | Ethane- on eich a, aly ane-1,2-diol 1 1 lycerol Proj > tr OH OH OH a Cyclic alcohols are named ree Onl geonp’atiarhed\t eee the prefix cyclo and consider OH OH ee Cyclohexanol 2-Methylcyclopentanol (b) Phenols: Th It is its pia hic nea hydroxy derivative of benzene is PI of pheaiayateats ea also an accepted IUPAC name. As st", terme OMmN(NS Caieubetitited Pes tee compounds! (1,4-disubstituted) are often used pees mcututed) a ommon names. Chemisti Scheme ae IM_PRABHU_AIMS_DELHI Intpsih-meomprabhuar ims OH CH, CH, CH, OH 3 OH * On Common name Phenol Cresol. crea v oe TUPAC name Phenol 2“Methylphenol “3-Methylphenol ~ 4-Meihylphenol Dihydroxy derivatives of { benzene are known as 1, 2-, 1, 3- 1, 4-benzenediol. » 1, 8- and OH OH OH OH OH -. ° ‘Common name ~Catecha) ’ Resorcinol Hydroquinone or quinol_ TUPAC name Benzene-1,2-diol Benzene- Benzene-1,4-diol (6 Ethers: Common names of ethers are derived from the names of alkeyl/ aryl groups written as separate words in alphabetical order and adding the word ‘ether’ at the end. For example, CH,0C,H, is ethyimethyl ether. Table 11.2: Common and IUPAC Names of Some Ethers Compound 3 ‘ Common name broom etty CH,OCH, Dimethyl ether Methoxymethane C.H.OC,H, Diethyl ether Ethoxyethane CH,OCH,CH,CH, Methyl n-propyl ether 1-Methoxypropane CcH,OCH, Methyl phenyl ether Methoxybenzene (Anisole) (Anisole) C.HJOCH,CH, Ethyl phenyl ether Ethoxybenzene (Phenetole) ‘CoHsO(CH,),~ CH, Heptyl phenyl ether 1-Phenoxyheptane ‘CH,O-CH - CH, Methyl isopropyl ether 2-Methoxypropane cH, GH.-O-CH,- CH,— CH-CH, Phenyl tsopentyl ether 3- Methylbutoxybenzene CH, CH;- O ~ CH, - CH, - OCH, H.C CH, 2-Bthoxy- 2 -1, 1-dimethylcyclohexane 1,2-Dimethoxyethane 2% Alcohols, Phenols and Ethers cohol, Lorre "hips youube.con/@OM_PRABHU_AIIMS,DELH! ‘ntps:/t elomprabhuaiimed Iboth the alkyl groups are the same. the prefix if is added Bee Far comaple, CHOC i cet! ether = Y the larger (R) group is chosen as the parent hye ‘The names of a few ethers are given as examples in Table 112 Give IUPAC names of the following compounds: @ CH,- CH - CH- CH- CH,OH in i 1 u 1 " SG Cl CH, CH, CH, : OH NO, a Co) tyr @ 4-Chloro-2,3-dimethylpentan-1-ol {@ 2-Ethaxypropane La: (i 2.6-Dimethylphenol Qv) 1-Bthaxy-2-nitrocyclohen 11.3 Name the following compounds according to IUPAC system. CHAOH CH.OH @ So, Cs, eS CA, 1 cH CH, cH, OH OH aOl. th H.C = CH-CH-CH,-CH,—CH, 9 CHC =C- CE ra OH CH, Br 11,4 flleakols and Phenols Alcohols, Phenols and pirate con 0M PRABHY AIS, DL Wee heeoaait *romatic ring. The carbon- oxygen bond Is slightly less than that i thi 4s due (4 (partial double:bord character on/account of then ase 1¢ conjugation 6 uniharet eelron Pair of oxygen. with: the aromatic ring ‘eon, brid altached-=) P=hybridised-state.of-caron-10- which: oxygen, 1 is bulky (-R) groups. The C-O bond length (141 pm) is almost the same as in alcohols, 11.4.1 Preparation of Alcohols Alcohols are prepared by the following methods: 1. From alkenes (i)\By acid catalysed hydration®\Alkenes react with water in the Sence of acid as Catalyst to form alcohols. In case of unsymmetrical alkenes, the addition reaction takes place in accordance with*Markovnikov's rule (Unit 13, Class XI) es ule Cl >e=c< + H,0 >e-c< H OH CH,CH=CH,+ H,0 = CH,-CH-CH, ~ I Mls a eOy OH Mechanism . The mechanism of the reaction involves the following three steps: Step 1: Protonation of alkene to form carbocation by electrophilic attack of H,0’. H,0 + H’ > H,O* H H | tee seeds + StH =C- CC +H8 Step 2: Nucleophilic attack of water on carbocation. H me, ¥ TS HO) =C- —O-H Step 3: Deprotonation to form an alcohol. H H ‘OH fe atthe H,O > Bone +H, ee " ew oxidation was firs _ reported by H.C. TD) Asibrrnstko tka Brown in 1959. For his studies on boron Bees a Bij fydroboration~oxidation containing organic re - |, -CH-Ck corps end ie CHeCH, + (N-BH),——> CH.CH-CH, shared the 1979 Nobel H BH, taniG wane” Jors-crecn, H=CH, (CH-cH-cHy,B 298" (cy,-cH,-cHy),BH 1,0] 31,0, OH 3CH,-CH,-CH,-OH + B(OH), Propan-I-ol _ Anifemaytent\4ov The addition of borane to the double bond takes place in a manner that the boron atom gets attached to the sp’ ca carrying greater number of hydrogen atoms. The alcohol so fo looks as if it has been formed by the addition of water t alkene in a way opposite to the Markovnik v's rule. In this reac sles ibang seen yl 2. From carbonyl compounds ( By reduction of aldehydes and ketones: Aldehydes and ket are reduced to the corresponding alcohols by additi hydrogen in the presence of catalysts (catalytic hydrogenats The usual catalyst is a finely divided metal such as platin adium or nickel. It is also prepared by treating aldeiiy nd Ketones with sodium Jprohydride (NaBH,) or lithi duminium hydride (LiAlH,)[Aldchydes yield primary alco: yhereas keiones give seconds RCHO +H, —& 5 RcH,OH 1° RCOR NaBH, ROHR’ 3 1H wn By reduction of carboxylic acids and esters: Caron r are reduced to primary alcohols in excellent yields be itt? aluminium hydride, a strong reducing agent. | (LAH, RCOOH ———s RCH,OH (wy H,0 re tion using hydrogen i" Presenee of catalyst (catalytic hydrogenaiiak drogenation). eon a: RCOOH——> RCOOR’ — 2, RopoH + RO! Catalyst ‘ntpsih-meomprabhuaimsd 3. From Grignard reagents / \ (\\ Alcohols are produced by the réaction of Grignard reagents (Unit 10, Class XI1) with aldehydes and ketones. The first step of the reaction is the nucleophilic addition of Grignard reagent to the carbonyl group to form an adduct. Hydrolysis of the adduct yields an alcohol. WOU : RAC Zo. eS SOLU Rex —5)>0- 0 Me-x LY R am) Adduct 1,0, 2C- OH + Mg(OH)x (ii) R ‘The overall reactions using different aldehydes and ketones are as follows: HcHo +BMex > RCH,OMex 2% Rop,OH + Mg(OHX Sermrenl dann’ 4 R R RCHO + RMX —> R-CH omex 225 p-GH_ on + Me(OHIX Krom Ndtadt ie a RCOR + R’Mgx ——> Re omgx 22> Re OH + Mg(OH)X Kakora, R Re You will notice that the reaction produces a primary alcohol with . . methanal, a secondary alcohol with other aldehydes and tertiary alcohol with ketones. Give the structures and IUPAC names of the products expected from — Example 11.2 the following reactions: ° (a) Catalytic reduction of butanal. "> ~/—~K\) : (b) Hydration of propene in the presence of dilute sulphuric acid. A, 4i_, {c) Reaction of propanone with methylmagnesium bromide followed thtPu by hydrolysis. RH cuquaty, 5a cH i

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