1、Organic Chemistry,1,Some significant organic chemical terms,hydrocarbons; saturated hydrocarbon; unsaturated hydrocarbon; conjugate (conjugation); （碳氫化合物，烴，飽和，不飽和，共軛）,Types of Reaction: substitution (alkylation, halogenation etc)（取代，如烷基化，鹵代）; addition（加成）; elimination（消去）; condensation（縮合）; polymeri

2、zation（聚合）; oxidation（氧化）; reduction（還原）.,2,degradation（降解）; rearrangement（重排）; replacement（置換） ; pericyclic reaction (cycloaddition reaction; electrocyclic reaction; sigmatropic rearrangement)（周環(huán)反應，包括:環(huán)加成，電環(huán)化，-重排）,Electrophile (electrophilic)（親電試劑，親電的）; nucleophile (nucleophilic)（親核試劑，親核的）; Carboca

3、tion（碳正離子）; carbanion（碳負離子）; radical（游離基，free ,自由基）; intermediate（中間體）; substituent（取代基）;,3,Reactivity（反應活性）; Attack（進攻）; leaving group（離去基團）; protecting group（保護基）; catalyst（催化劑）; Kinetic（動力學的）; thermodynamic（熱力學的）.,cis-trans isomer; optical isomer (enantiomer); （順-反異構體，光學異構體（光學對映體） asymmetric; chi

4、ral; chirality; （不對稱，手性的，手性）,4,racemic mixture; meso compound; （外消旋體，內(nèi)消旋體） stereoselective reaction; stereospecific reation; regioselective reaction; steric hindrance; steric effects; （立體阻礙（位阻），立體效應 ）,5,reflux; stir; azeotrope; （回流，攪拌，恒、共沸物） separation; filter; distillation; fraction; chromatography

5、; （分離，過濾，蒸餾，分餾，色譜） extraction; precipitate; recrystallization; （萃取，沉淀，重結晶）,Terms related to the synthetic experiment,6,7,8,Ground joint; Flask (three-necked, round-bottom, conical, filter, suction, volumetric); Condenser (air, reflux, ball, coil); distilling head (claisen); adaptor (vacuum); Beaker;

6、 funnel (buchner, separatory, long-stem, stemless, dropping, sintered glass); Bottle (weighing, washing, dropping, gas-washing); drying tube (tower, desiccator, vacuum desiccator);,9,Prefix-Parent-Suffix Nomenclature of parent part-Nomenclature of alkanes and alkyl substituents Straight-chain alkane

7、s Straight-chain alkanes are named by counting the number of carbon atoms in the chain and adding the family suffix-ane. Thus pentane is the five-carbon alkane, and hexane is the six-carbon alkane.,10,An alkyl substituent (or an alkyl group) is an alkane from which a single hydrogen has been removed

8、. Alkyl substituents are named by replacing the “ane” suffix of the alkane with “yl”. The letter “R” is used to indicate any alkyl group. Thus CH3- has the name of methyl, while the group of CH3CH2- was named ethyl.,11,Number Molecular Name Name in Alkyl of carbons formula Chinese substituents 1 CH4

9、Methane甲烷 Methyl 2 C2H6Ethane乙烷 Ethyl 3 C3H8Propane丙烷 Propyl 4 C4H10Butane 丁烷 Butyl 5 C5H12Pentane戊烷 Pentyl 6 C6H14Hexane己烷 Hexyl 7 C7H16Heptane 庚烷 Heptyl 8 C8H18Octane辛烷 Octyl 9 C9H20Nonane壬烷 Nonyl 10 C10H22Decane癸烷 Decyl 11 C11H24Undecane十一烷 Undecyl 12 C12H26Dodecane十二烷 Dodecyl 13 C13H28Tridecane十

10、三烷 Tridecyl 20 C20H42Icosane二十烷 Icosyl 21 C21H44Heneicosane二十一烷 Heneicosyl 30 C30H62Triacontane三十烷 Triacontyl,12,Branched-chain alkanes 3-ethyl-3-methylhexane,13,Some useful prefixes for indicating the number of substituent groups Mono-單取代, 一取代 Di- 二取代 Tri-三取代 Tetra-四取代 Pent (a)-五取代 Hex (a)-六取代 Hept

11、 (a)-七取代 Oct (a)-八取代 Nona-九取代 Deca-十取代,2,6-dimethyloctane not 2-ethyl-6-methylheptane 3-ethyl-2-methylhexane not 3-isopropylhexane,14,Some useful prefixes used to name branched alkanes (Common names) (normal) n- 正 (isomer) iso- 異 neo- 新 primary 伯，一級 (secondary ) sec- 仲，二級 (tertiary) tert- 叔，三級 quate

12、rnary 季，四級,n-pentane neopentane isobutane 正戊烷 新戊烷 異丁烷 Pentane 2,2-dimethylpropane 2-methylpropane tert-butanol isobutanamine sec-butanamine 叔丁醇 異丁胺 仲丁胺 2-methyl-2-propanol 2-methylpropanamine 1-methylpropanamine,15,Cyclic alkanes (cycloalkanes) e.g. cylcopropane, cyclopentane, and cyclohexyl etc,16,

13、Nomenclature of acyclic hydrocarbons with one double or triple bond Acyclic hydrocarbons having one double or triple bond are named by replacing the ending “-ane” of the name of the corresponding alkane with the ending “-ene” or “-yne” . (alkene) (alkyne) e. g. (butane) butene butene butyne trans-2-

14、butene cis-2-butene 3-methyl-1- butyne,17,The univalent radical derived from acyclic alkene or alkyne has the endings “-enyl” or “-ynyl”, (alkene alkenyl) (alkyne alkynyl), and the position of the double or triple bond is indicated where necessary. (unlike alkane alkyl) e. g. 1-propenyl 2-butenyl et

15、hynyl 2-propynyl,18,The following non-systematic names are retained Ethylene (乙烯） Allene （丙二烯） Acetylene （乙炔） Isoprene （異戊二烯） Vinyl （乙烯基） Allyl （烯丙基） Isopropenyl （異丙烯基）,19,Nomenclature of acyclic hydrocarbons with two or more double or triple bonds Two or more double bonds: the ending will be “-adie

16、ne”, “-atriene” etc. (alkadiene) Two or more triple bonds: the ending will be “-adiyne”, “-atriyne” etc. (alkadiyne) e. g. 2-methyl-1,3-butadiene propadiene 2,5-dimethyl-2,4,6-octatriene 3-ethyl-4-methyl-1,6-heptadiyne,20,Nomenclature of monocyclic aromatic hydrocarbons 苯 甲苯 二甲苯 苯乙烯 異丙苯 均三甲苯 benzene

17、 toluene xylene styrene cumene mesitylene 苯基 甲苯基 二甲苯基 苯乙烯基 異丙苯基 均三甲苯基 芐基 Phenyl tolyl xylyl styryl cumenyl mesityl benzyl,21,Common names retained for the disubstituted benzene ortho-, o-鄰 meta-, m-間 para-, p-對,m-methylbenzyl m-tolyl 3,4-dimethylphenyl 3-methylbenzyl 3-tolyl o-styryl p-cumenyl 3,5-d

18、imethyl-4- ethylphenyl 2-styryl 4-cumenyl,22,Some important Families of organic molecules Saturated hydrocarbons: such as: Alkanes; cycloalkanes; Un-saturated hydrocarbons: such as: alkenes; alkynes; cycloalkenes; cycloalkynes; cycloalkadienes; cycloalkadiynes; Aromatic compouds: benzene; biphenyl;

19、naphthalene and other fused and polycyclic aromatic hydrocarbons; Compounds with functional groups: alkyl halides （鹵代烴）; alcohols（醇）; phenols（酚）; ethers（醚）; amines（胺）; Compounds with functional groups: aldehydes（醛）; ketones（酮）; quinones（醌）; carboxylic acids（羧酸）; esters（酯）; acyl halides（酰鹵）; acid anh

20、ydrides（酸酐） amides（酰胺）; imides（亞胺）;,23,Compounds with functional groups: alkyl halides （鹵代烴）; alcohols（醇）; phenols（酚）; ethers（醚）; amines（胺）etc. alkyl halidesR-X halogen (-halo) (-Cl, -Br, -F, -I) AlcoholsR-OH hydroxy group (-OH) PhenolsAr-OH hydroxy group (-OH) EthersR-O-R Alkoxy group (O-R) AminesR

21、-NH2 amino group (NH2),24,Alkyl halides (haloalkane or alkyl halide) Alkyl halides are classified as primary, secondary, or tertiary depending on the carbon to which the halogen is attached.,25,The common names of the alkyl halides are obtained by citing the name of the alkyl group followed by the n

22、ame of the halogen. (alkyl halide) In the IUPAC system, alkyl halides are named as substituted alkanes. The substituted prefix names for the halogens end in “o”(fluoro, chloro, bromo, iodo). (haloalkane),26,Nomenclature of alcohols Alcohols The common names, similar to alkyl halides, are obtained by

23、 citing the name of the alkyl group to which the OH group is attached, followed by the word “alcohol”. (alkyl alcohol) The IUPAC name for an alcohol is obtained by removing the “e” from the name of the alkane and adding the suffix “ol”. (alkanol),27,Nomenclature of amines Amines are compounds in whi

24、ch one or more hydrogen of ammonia have been replaced by alkyl groups. There are primary, secondary, and tertiary amines. This classification depends on how many alkyl groups are bonded to the nitrogen. (!not carbon),28,The common name of a amine is obtained by citing the names of the alkyl groups b

25、onded to the nitrogen in alphabetical order. The entire name is written as one word. (alkylamine) e. g.,29,There are two IUPAC approved way to name an amine. It can be named as a substituted alkane using the prefix “amino” to designate the amine substituent. (?aminoalkane) It also can been named wit

26、h a functional group suffix- “amine”. The “e” at the end of the alkane name is replaced by “amine”. The names of substituents bonded to the nitrogen are preceded by an N (in italic) to indicate that the substituent is bonded to a nitrogen rather than to a carbon. (N-alkyl)alkanamine,30,31,Amines wit

27、h four alkyl groups bonded to the nitrogen-and therefore a positive charge on the nitrogen-are called quaternary ammonium salts. Their names are obtained by citing the names of the alkyl groups in alphabetical order as a prefix to “ammonium”, followed by the name of the counterion. alkylammonium hal

28、ide (or hydroxide etc),32,Nomenclature of ethers symmetrical ether and asymmetrical ether. e. g.,33,The common name of an ether is obtained by citing the names of the two alkyl substituents (in alphabetical order) followed by the word “ether”. The smallest ethers are almost always named by their com

29、mon names. ( alkylalkyl ether) The IUPAC system names an ether as an alkane that bears an alkoxy substituent. Alkoxy substituents are named by removing the “yl” from the name of the alkyl substituent and adding “oxy”. (alkoxyalkane),methoxy,ethoxy,1-methylethoxy,1,1-dimethylpropoxy,34,A carbonyl gro

30、up （羰基） is a carbon doubly bonded to an oxygen and an acyl group （?；?is a carbonyl group attached to an alkyl substituent. A benzoyl group （苯甲?；?is a carbonyl group attached to a benzene ring.,35,Nomenclature of aldehydes and ketones The common name of an aldehyde is the same as carboxylic acid (d

31、erived from some Latin words). (Latin+aldehyde) The IUPAC name of an aldehyde is obtained by removing the “e” from the alkane name and adding “-al”. (alkanal),36,If the aldehyde group is attached to a ring, the aldehyde is named by adding “carbaldehyde” to the name of the ring. (cycloalkanecarbaldeh

32、yde),phenylmethanal,37,Nomenclature of ketones Common name: Only a few ketons have common names, such as acetone (like aldehyde). Common names are also used for phenyl-substituted ketones. They are called phenones. (+ one) IUPAC name: Ketones are named in the IUPAC system by removing the “e” from th

33、e alkane name and adding “-one”. (alkanone) Derived name: Like ethers, R-CO-R can be named by citing the names of the two alkyl substituents (in alphabetical order) followed by the word “ketone”. (alkylalkyl ketone),38,Common name IUPAC name Derived name,39,Nomenclature of carboxylic acids and its d

34、erivatives,X= OH, a carboxylic acid X= halogen, an acyl halide X=OR, an ester X= OCOR, an acid anhydride X= NRR, an amide,40,Nomenclature of carboxylic acids a carboxyl group The functional group of a carboxylic acid is called a carboxyl group. Long-chain carboxylic acids are called “fatty acids”.,4

35、1,Common name: Carboxylic acids (6) are frequently called by their common names. They are named by adding “Latin prefix” before “acid”. ? what is carbon? IUPAC name: a carboxylic acid is named by replaceing the “e” ending of the alkane name with “oic acid”. (alkanoic acid) Carboxylic acids in which

36、a carboxyl group is attached to a cyclic compound can be named by adding “carboxylic acid” to the name of the cyclic compound.,42,benzoic acid,43,Nomenclature of acyl halides Acyl halides are named by using the acid name and replacing the “ ic acid” with “ yl halide” (alkanoyl halide) , or by replac

37、ing “ carboxylic acid ” with “ carbonyl halide ” (cycloalkanecarbonyl halide),44,benzoyl chloride,45,Nomenclature of acid anhydrides ? Do you know the meaning of “anhydride” R = R, a symmetrical anhydride R R, a mixed anhydride,46,Symmetrical anhydrides are named by using the acid name and replacing “acid” with “anhydride”, mixed anhydrides are named by stating the name of both acid group