Detailed Nomenclature

Detailed Nomenclature - You are expected to teach yourself...

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Unformatted text preview: You are expected to teach yourself organic nomenclature! Begin as soon as possible, Everything you learn concerning the naming of organic compounds will be used in lectures, reading assignments, problem sets, and examinations in this and subsequent chemistry courses. FOr this section of this course, you will be required to write a structural formula given a name but not the reverse, This material is relatively simple and straightforward but learning nomenclature will require intensive study. This worksheet will help supplement the first problem set and reading assignment. 1. Wm (contain only C, H) 1. Alkanes (aliphatic hydrocarbons) CnH2n+2 , suffix an: open chain (non cyclic --- also called acyclic) can have branches, are saturated (no double bonds) (a) normal or linear hydrocarbons CH4 methane, CH3CH3 ethane, CH3CH2Cl-l3 propane, CH3(CH2)2CH3 butane, pentane, CH3(CH2)4CH3 hexane, CH3(CH2)5CH3 heptane, CH3(CH3)6CH3 octane, CH3(CH2)7CH3 nonane, CH3(CH2)8CH3 decane. Alkyl (hydrocarbon) groups, symbolized by R, suffix y_l_. One hydrogen in an alkane replaced by some other group or atom. Examples: CH3 - methyl, CH3CH2 - ethyl, CH3CH2CH2 - n-propyl (or l-propyl), CH3CHCH3 Lsg-propyl (or 2-propyl), CH3CH2CH2CH2 - n-butyl, CH3CHCH2CH3 sec-but 1, 3*“ 9H3 y . CHgCl-lCl-lz-isobutyl, CH3-C'I- t_e_rt-butyl CH3 CH3CH2CH2CH2CH2- n-pentyl, also n-hexyl, heptyl, octyl, nonyl, decyl. (IUPAC) System and common variations for naming alkanes: longest continuous hydrocarbon chain is selected as root or base and branches are designated by alkyl groups with a prefixed number designating the position. Use lowest numbers. EXAMPLE: C position of ethyl group 5-_emyl-3,3-dimemylh9pt&ne CH3 CH CH 2 3 alkane I I m 1 CH3CH2—C—CH2—CH—CHZCH3 No m y I groups CH3 1 2 3 4 5 6 7 7carbon chain \ _ / contain IC_C\ ,are unsaturated), simple systems CHI-12“, suffix gm. Use the lower numbered olefinic carbon to designate the position of the double bond. N 2 7? (n :3 a m A 9.. CD :21 :1 f” Examples (IUPAC system) CHSCH2CH2CH=CHCH3 CH3CH2CH2CH=CH2 2-hexene (isomers possible ' here, at this stage undesignated) l-pentene CH3 CH3-éH—CH=CH2 3-methyl-l-butene Examples common names: CH2=CH2 ethylene, CH3CH=CH2 propylene (CH3)2C=CH2 isobutylene, (CH3)2C=C(CH3)2 tetramethylethylene There are also dienes (2 C=C) and triene, etc. Example: CH2=CH-CH=CH2 1,3-butadiene (a Wdiene) CH3 _ I _ _ . CH2=CH—CH2 _C=CH2 CH2—C —CI~I2 (a gummulated dJene) 1 ,2-propadiene 2-methyl-1 ,4-pentadiene or allene (not conjugated diene) Cyclic olefins: 3-methyl-l -cyclopentene . ' Or 3—methylcyclopentene CH3 cyclobutene C(CH3)3 l-flbutyl-l ,4-cyclohexadiene Special alkene groups: CH2=CH— vinyl CH2=CH-CH2- allyl 3. Aromatic Hydrocarbons (arene). Derivatives of benzene whose structural and electronic properties are n_o_[ those expected for a cyclic conjugated Uiene. H ‘ H H H = H H H H H H H H benzene 1,2-disubstitution referred to as ortho (0-) 1,3-disubstitution referred to as meta (m-) 1,4-disubstitution referred to as para (p-) Examples with common names in parentheses: CH3 CH3 CH3 CH3 (2 E 1 - CH3 CH3 methylbenzene laz'dlmethyl' (m‘xylene) p-xylene (toluene) benzene (o-xylene) 4. Alkynes (acetylenes, “CE-C“ , two sites of unsaturation), simple systems CnH2n_2, suffix Ln; CH3 . | . TUPAC example- CH3—CH-CH2-CH2-CECH CH3-C=_C-C=_C-C:—C-CH3 5-methyl-l-hexyne 2,4,6—octam'yne (a conjugated system) CH3 Common nomenclature based on acetylene (HCECH ): CH3_éH_CEC_CH3 Special alkynyl group: HCEC— = ethyny] isopmpylmemylacetyleue 5. Alicyclic compounds (hydrocarbon rings) simple systems CnHzn, prefix cyclo , each cycle represents one "site of unsaturation" but not actual unsaturation (multiple bonding). ‘ CH3 Examples; CH2 5 A ' 1,3-dimethylcyclopentane . / \ (isomers possible here: so far CH2 CH2 not designated) cyclopropane CH3 Cycloalkyl groups: CH=CH2 ijclohexyl, etc. ' . CH Vinyl benzene I 3 (styrene) H CH3—C—CH2CH2CH =CH2 H H henyl group 5-cyclohexyl-5- p methyl-l -hexene H H (3171 group) H H H H CH3—CH-CH2CH2CH3 ALSO: H E H H H H 2-phenylpentane or naphthalene c32— 2-pentylbenzene O benzyl group H. Functional Grou s atur e r on 6. Organic halides: Halogen (fluorine F, chlorine C1, bromine Br, and iodine I) can be substituted for hydrogen. Use alkyl halide or halo-alkane. Examples: CH3}: methyl fluoride BrCHzCHzBr 1,2-dibromoethane (CH3)3CC1 te_n_-buty1 chloride Cal—(Inacmcn2 3-bromo-1-butene / Br 0‘ B' ’ ' 3_- d 1 t 1,3—dibromobenzene 10 ocyc open ene a (m-dibromobenzene) CHzl Br Obenzyl iodide CH2==CHC1 vinyl chloride Common halides: CC14 carbon tetrachloride HCC13 chloroform F(CF2)nF teflon (n very large) 7. Alcohols ROH, suffix g1, occasionally use hydroxy + alkyl root or alkyl + alcohol. Examples (IUPAC) common name in parentheses: CH30H methanol OH CH3CH2CH2CHZOH CH2=CHCH20H Ox 1 'bmanOl 2-propen- 1 -ol 1 t l (n-butanol or n-butyl alcohol) (5111),} alcohol) E3;C?:;:nil;lloak0hon CH2=CH-CH2-$H—CHZOH 4-penten-l ,2-diol OH Special terms: Primary alcohol - RCHZOH e.g. ethyl alcohol CH3CH20H Secondary alcohol - RleCl-IOl-I e.g. isopropyl alcohol (CH3)2CHOH Tertiary alcohol - R1R2R3COH e.g. Len-butyl alcohol (CH3)3COH (see also amines for primary, secondary, tertiary) 0H phenol (treated as a special class of alcohols) note i unsamration at carbon 5 Carbinol system: name as derivatives of CH3OH methanol or carbinol OH e'g' | dimethylcarbinol CH CH3—C—CH3 (isopropyl alcohol) or $ 3 IL 2-propanol CH3 dimethylphenylcarbinol Special alcohols: HOCHz—CHCHZOH HOCHZCHZOH ethylene glycol ~ _ (a vi cina! diol) adjacent carbons glycenn 0H substituted ‘3“ ll CH3-C|?H __:_’ CH3-CH + H20 OH acetaldehyde 1,1-ethandiol A gem diol (unstable with respect to loss of H20); disubstitution on the same carbon 0 CH2=CHOH ——:: CH‘JJm vinyl alcohol acetaldehyde (unstable with respect to tautomer) 8. Ethers ROR named by alkyl or aryl groups then ether Examples: CH3OCH2CH3 CH3CH20CH2CH3 diethyl ether methyl Ethyl Ether (simply referred to as ether) OCH3 ©(phenyl methyl ether SpeCial Cases: CHz—CHz (anisole) \ / ethylene O oxide (an "epoxide") Ethers: Special cases, continued. CH2—CH2 l l tetrahydrofuran O dioxane CH2 CH2 [0] \/ O 9. Amines: derivatives of ammonia (NH3) Primary RNHZ name alkyl (or aryl) groups with suffix amine Secondary R1R2NH CH3 .0 .. I .. Tertiary R1R2R3N examples: CH3CH2NHCHCH3 (C6H5)2NH ethylisoprOpylamine diphenylamme (EH3 benzylmethyl-t- Special class quaternary (CH3)3C—I;I.—-CHZC6H5 bmylamme ammonium salts: derivatives of armnonium ion, Nl-l4+ e-g' CH3 dimethylethylphenyl ammonium chloride I + _ (:Ii3"'lr"'(:6}i5 (:1 QB; fin: (j aminobenzene (aniline) H-ixicn3 55112 Also used as prefix amino: C1 . . CH<CH3>2 E—memyl—m-chloroamhne (note use of _l§l_ to designate substitution on nitrogen) l-amino-3-(2—propyl)—cyclohexane (stereochemistry not designated) CH3—N-CH3 1-(fl,N_—dimethylamino)-3,S-dihydroxybenzene HO OH Special case: HZNNHZ hydrazine CH3NHNI-ICH3 JEN-dimethylhydrazine ( note use of a prime to designate the second N) 10. Sulfur compounds (analogues of alcohols and ethers) RSH a thiol or mercaptan suffix thiol or alkyl + mercaptan. c1 4-chloro- ] -pentanethiol e.g. (CH3)2CHCHZSH . isobutyl mercaptan CHs—CH-CH2CH2CH25H RSR‘ sulfides: C6H5CHZSCH2C6H5 dibenzyl sulfide . 0 . Note also further classes: R-S-S-R a disulfide; R—é—R a SUIfox‘dea O 1". R—g—R 5‘ sulfone; R—T-R a sulfonium salt I 0 R 111. Functional Groups Unsaturated at Carbon 11. Carboxylic Acids RC02H suffix gig followed by acid ACID IUPAC COMMON O H_I(I:OH methanoic acid* formic acid CH3C02H ethanoic acid* acetic acid CH3CH2C02H propanoic acid* propionic acid CH3CH2CH2C02H butanoic acid* butyric acid CH3CH2CH2CH2C02H ' pentangic acid * These names are seldom used 0 Also can designate -C02H group by prefix carboxy: CC cozn 2-carboxycyclohexanone Another method alkyl + carboxylic acid: COZH Q/cyclopenMecmboxyfic acid Special cases: COZH g C") mnedio‘.» ac; J ‘ benzoic acid HO-C_C_OH oxalic acid 0 O 0 0 H H II C II HO~C~CH2-C—OH HO— "CHz-CHz—C-OH BrCHZCH2C02H malonic acid succinic acid B-bromopmpionic acid Pml’medm“ “cm bulzmedioc ac‘iol use of 0t,[3 etc. yentzmedm C a CM Wanediu 3c acid usua— madam add (fil ufunoacfd) (“spin acid) Cmaleicam) _ 0 Vans ’3 ” bu Pal iolc 90ml ” C man’c acid 12. Aldehydes R-C—H suffix a1 (note always on car on 1) also carboxylic acid root + aldehyde (-carboxaldehyde) (see below) Examples: 0 methanal (IUPAC name) H_g__H formaldehyde (as derivative of carboxylic acid) CH3CH2CH2CH2CHO CH0 CH3CHO ntanal ethanal p6 cyclobutylmethanal (acetaldehyde') . (EH3 0 CH2=C—CHo ” CHO FCHZCHQCH 2-methylpropenal 0’ (Note it is unnecessary to 3-fluoropropanal number the olefinic carbon) (B-fluoropropan aldehyde) ' benzaldehyde see later section for use of (143 etc 9 O 13, Ketones R_'CI_R IUPAC suffix _o_n§ with number designation for the longest chain containing the functional group ketone system: name each alkyl group, add mi; . 0 Examples" propanone (note number not necessary here) CH3—C—CH3 dimethylketone: acetone (this common name 0 almost always used) ll ' O CH3CH=CHCH2C—CH3 3-bromocyclopentanone 4—hexene-2-one (note isomers possible but Br CH3—C—CH2CH3 n0! deSigDath) butanone (number not required) i) (methyl ethyl ketone) CH =CH-C_CH 3-butene-2-one 2 3 methyl vinyl ketone ii 14, Cmboxync esters R_C_ORv (derivatives of acid RCOZH and an alcohol R'OH) name alcohol function first, use acid name dropping oic and use suffix at; 0 o g OCH ” /CH3 CH3_ 3 crigcnzcnzcnzcn2 -—C--O-CH \ CH3 meth l acetate , ._ v y vvkdeSlgnates l propyl hexanOfltC f ester C1 0 alcohol .d I ll portion Simon CH2=CH—CH2 ~CH —C-OCH2 benzyl-2-chloro—4-pentenoate lO cyclic esters are called la_ct_o_r_te_s a The position of the alcohol oxygen is designated by a Greek letter B O (I? (I? B-propiolactone 15. Carboxylic Anhydrides: R—C-O—C—R (only the symmetric cases are commonly encountered) Use acid name replace "carboxylic acid" by W O ‘ ~O CH1_ICI_O_£_CH1 acetic anhydride 0 || 16. Acid Halides: RCX (X = F, Cl, Br, I) only chlorides commonly encountered. IUPAC or common name of acid followed by suffix yl_ orgfl halide. 0 Example: . CH3—C_C1 acetylchloride 17. Amides: Derivatives of carboxylic acids and amines (nitrogen relatives of esters ii if i? R~C—NH2 R‘—C—"NHR' R—C—NR'R' UDSUbSdtuted monosubsdtuted djSUbStituted Name amine component then acid root suffix amide, Examples: (I? (I? CH3—c—NH2 CHgCHz—C-NHCHZCHg acetamide H-ethylpropionamide O H CH3 / . . H—C—N\ fl-mmethylfomamde (DMF) 11 Cyclic amides are called lactams nomenclature is similar to lactones. [k N-phenyl-y-butyrolactam O . N Example: IV. W R-CN njnfles or cyanides named as derivatives of the carboxylic acid having the same number of carbons m as cyano group. Examples: CH3CN acetonitn'le NCCHZCHZOH B-cyanoethanol or 2-cyanoethanol RN02 nitro compounds-—-use group designation nitro: CH3 OZN N02 2,4,6-trinitrotoluene (TNT) No2 Imides: (I? H (I? nitrogen analogues of anhydrides l R—C—N—C—R if CH c . 2 \ succinimide NH (a cyclic imide) fi/ 0 CH2 There are many more groups that have been omitted from this list. Note and learn these as you encounter them. 12 . V. Special terms (a) Greek letters used to designate position of derivatives with respect to root functional group. 0t B 'y 5 etc. ExamP1653CICH2CHZOH CH3—(l'IH-OCH2CH3 a-cyanoethylethyl B-Chloroethanol NC ether ll CH3—CH—C—OH a-bromOprOpanoic acid 1'3, ' Note: on is lst carbon, adjacent to the carbonyl group O NH B-caprolactam (note 6 carbon acid is caproic acid) CH3 (b) .éCH a, methylene n = 1, dimethylene n = 2, etc. 2 n Example: HZNCHZCHZCI-lzCHZNHZ tetramethylene diamine l3 ...
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Detailed Nomenclature - You are expected to teach yourself...

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