ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA. ANA 2009ACTIVITY 5: ORGANIC DERIVATIVES OF WATEROrganic derivative of water are formed by replacing the hydrogen atom with alkyl group which results tothe formation of alcohol, phenol, or ether as illustrated in below. Alcohol is a polar compound since it is capable offorming H-bonds with water. Phenol, an aromatic alcohol, can also form such H-bond but the presence of thenonpolar benzeneringlimitsitssolubilityinwater. ther hasnet dipolemoment duetoitsbent structure,however, it cannot form H-bonds with water making it practically insoluble in water. Nomenclature of Alcohols!he hydro"yl #-OH$ group of alcohol is given priority as such the follow the given rules when naming alcohols.#%$ &ind the longest continuous carbon chain that includes the hydro"yl group. 'umber the parent chain in such a way that gives the lowest number to the carbon where (OH is attached.#)$ !he parent chain is named by replacing the suffi" ane of the corresponding alkane with ol.#*$ 'ame the other substituents in alphabetical order and indicating their position on the parent chain.#+$ ,f the hydro"yl group is attached to a ring, the numbering always starts with the (OH and continues in the way that gives the lowest numbers to the other substituents.#-$ .hen multiple number of hydro"yl groups are present, the suffi" -diol, triol-, -tetraol, etc. is used to indicate their number.#/$ .hen the parent chain contains a double or triple bond, the hydro"yl group is still given the highest priority.!he number that indicates the position of the multiple bonds is placed in front of the hydrocarbon root name.!he number that indicates the position of the hydro"yl group is appended to the name of the hydrocarbon chain along with the suffi" ol.1Samle E!erc"se #: 'ame the given alcohol.OHBr15-m!"#$2%5&'( )%-*r+m+&-,r+,#$$%&romo%5%meth'l%(%ro'l%)%octanol*ract"ce E!erc"se #: 0raw the structure of /-chloro-)-isopropyl-*-ethyl-%,1-heptadiolESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA. ANA 2009Nomenclature of *henols!he naming of phenols follows the naming system in aromatic compounds which is summarized below.#%$ !he numbering on the benzene ring always starts with the hydro"yl group and continues in such a way that gives the lowest numbers to the other substituents.#)$ !he substituents are named alphabetically and the parent chain is named as phenol.-%. &or disubstituted compounds, use the prefi" ortho-, meta-, or para- to indicate the position of the substituent.2Samle E!erc"se ): 0raw the structure of *-tert-butyl-+-cyclohe"en-cis-%,)-diol.OHOH*ract"ce E!erc"se ): 'ame the given alcohol.HOOH OHOHSamle E!erc"se $: 'ame the given phenolic compound.CH%HOBr12%&5(%-*r+m+&-m!"#$$%&romo%(%meth'lhenol*ract"ce E!erc"se $: 2esorcinol is an antiseptic and disinfectant that is used in treatment of psoriasis and eczema.,ts systematic name is meta-hydro"yphenol, draw its structure.ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA. ANA 2009Nomenclature of Ethersthers can either be symmetrical or asymmetrical in nature.3ymmetrical ethers have the same alkyl groups attached to either side of o"ygen while asymmetrical ones have different alkyl groups.thers are named either by their common or traditional names or by their systematic name according to ,4PA5 rules which are stated below.#%$ &or their common name, ethers are named as alkyl alkyl ethers.!he name of the alkyl groups are listed according to alphabetical order and then appending the name ether.&or symmetrical ether, the prefi" di- is used in con6unction with the alkyl group.#)$ &or their ,4PA5 name, ethers are named as alkoxy alkanes.!he smaller alkyl group and the o"ygen atom is the one named as alkoxy, and is thus treated as substituent of the larger alkyl chain.ACTIVITY +5%Samle E!erc"se (: 'ame the given ether both in the traditional and ,4PA5 system.O11 22%%&5&(Tra,"t"onal: &ut'l c'clohe!'l etherI-*AC: &uto!' c'clohe!ane *ract"ce E!erc"se $: 0raw the structure of cyclopentyl phenyl ether and give its ,4PA5 name.HOOHOHOHCH%OOHOHOOOHHOOOHOOOESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA. ANA 2009ORGANIC DERIVATIVES OF WATER'A78 99999999999999999999999999999999999999999999999999 35O28 99999999999935!,O'899999999999:A;O2A!O2< ,'3!245!O289999999999999999999999999999999999999999A. 'ame the following compounds #)= pts$%.

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).1.*. >. +. ?. -.%=. ;. 0raw the structure of the following organic derivatives of water. #)= pts$&ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA. ANA 2009%. .%c'clohe!'l%trans%/%nonen%#0)%,"ol/.2,5-,"metho!'%(%h',ro!'henol2. trans%)%&uto!'%(%"soro'lc'cloentanol 1.,"%$%meth'lc'loent'l ether*. #1%un,ecaen%/%'ne%)%ol >.)%meth'lroano!'% all trans%#0$%enta,"ene+. #0$0502%c'clooctatetraen%#0$0502%tetraol ?.$05%,""soroano!'c'clohe!ene-.para%#%roeno!'henol %=. para%c'clohe!ano!'henol5ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA. ANA 2009E3*ERI4ENT +5: ORGANIC DERIVATIVES OF WATERAlcohols can be classified based on the number of alkyl groups attached to the carbon that contains thehydro"yl group as illustrated below.ach type of alcohol has different reactivity towards various reagents. Primary and secondary alcoholsreact with various o"idizing agents while tertiary alcohols are unreactive.On the other hand, tertiary alcohols aremost reactivetonucleophilicsubstitutionin:ucasreagent whilesecondaryalcoholsare@uitereactiveandprimary alcohols are unreactive.!he presence of benzene ring makes phenol more acidic than comparable cyclicand acyclic alcohols. Phenols are o"idized only by the strongest o"idative agents. A useful chemicaltest fordifferentiating phenols from alcohols is via ferric chloride test. thers are generally unreactive as it is a very stablebond.O&5ect"6es,n thise"periment, youwill be able to distinguishthe difference among variousorganic derivatives ofwater based on their characteristic solubility behavior and reactions.4sing this knowledge, you will understandhow to identify unknown samples of alcohols, phenols, or ethers. 4ater"als an, Rea7ent?-A thanol 4nknown sample % :ucas reagent !est tubes)-;utanol 4nknown sample ) %A &erric chloride Pasteur pipettestert-butanol 4nknown sample * 0istilled waterPhenol ;ayerBs reagent %.==7 'aOH0iethyl ether %.==7 'a)5r)O1 5onc. H)3O+*roce,uresP25A4!,O'38 Phenol, concentrated sulfuric acid, sodium dichromate, and 'aOH are corrosive substances.Avoid direct skin contact.0iethyl ether vapour is to"ic, avoid inhalation.%. Place - drops %-butanol, )-butanol,tert-butanol, phenol, diethylether, and each of the unknown samples onseparate dry test tubes.Prepare new set of samples for each of the test below8a. 3olubility in water( add - drops of distilled to each sample.3hake and then observe solubility.b. 3olubility in 'aOH ( add - drops of 'aOH to each sample.3hake then observe solubility.c. ;ayerBs o"idation ( add - drops of ;ayerBs reagent.3hake and observe the reaction.d. 5hromic acid o"idation ( add - drops of 'a)5r)O1 and * drops of conc. H)3O+.Observe the reaction.e. :ucas test ( add %= drops of :ucas reagent.3hake and observe the reaction for about --%= minutes.f. &erric chloride test ( add - drops of ferric chloride.3hake and observe the reaction.). ,dentifytheunknownsamplesbycomparingtheirsolubilityandreactionprofileagainstthat of the knowncompoundsSC8E4ATIC DIAGRA4(ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA. ANA 2009E3*ERI4ENT +5: ORGANIC DERIVATIVES OF WATER DATA S8EET'ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY GIDEON A. LEGASPI, SUSAN T. STA. ANA 2009E3*ERI4ENT +5: ORGANIC DERIVATIVES OF WATER'A78999999999999999999999999999999999999999999999999999999999999999935O2899999999935!,O'89999990A! P2&O2708999999999999 ,'3!245!O2899999999999999999999999999999A9 Solu&"l"t' an, React"on *rof"le :$1ts;Solu&"l"t' "n8)OSolu&"l"t'"n NaO8