G-5 GLOSSARY ond-line formula (Section 1.7): Formula in which connec- Carboxylate ion( Section 19.5): The conjugate base of a car tions between carbons are shown but individual carbons boxylic acid, an ion of the type RCO2 and hydrogens are not The bond-line formula Carboxylation (Section 19. 11): In the preparation of a car- boxylic acid, the reaction of a carbanion with carbon diox ide. Typically, the carb RMgX RCOH presents the compound (CH3)2 CHCH,CH3 undary surface(Section 1. 1 ) The surface that encloses the Carboxylic acid(Sections 2.3 and 19.1): Compound of the typ region where the probability of finding an electron is high (90-95%) Branched-chain carbohydrate (Section 25.12): Carbohydrate RCOH. also written as RCO, H. which the main carbon chain bears a carbon su Carboxylic acid derivative (Section 20. 1): Compound that in place of a hydrogen or hydroxyl gre yields a carboxylic acid on hydrolysis. Carboxylic acid de- romohydrin( Section 6.17): A halohydrin in which the halo- rivatives include acyl chlorides, anhydrides, esters, and gen is bromine(see halohydrin) amides Bromonium ion(Section 6.16): A halonium ion in which the Carotenoids (Section 26. 16): Naturally occurring tetrater halogen is bromine(see halonium ion). peroid plant pigments Bronsted acid See acid Cation (Section 1.2): Positively charged ion. Bronsted base see base Cellobiose (Section 25. 14): A disaccharide in which two glu Buckminsterfullerene(Chapter 11, box, "Carbon Clusters cose units are joined by a B(1, 4)linkage Cellobiose is ob Fullerenes, and Nanotubes"): Name given to the Cso cluster tained by the hydrolysis of cellulose. with structure resembling the geodesic domes of R. Buck- Cellulose(Section 25. 15): A polysaccharide in which thou- Ister Fuller. see front cover sands of glucose units are joined by B(1, 4) linkages. n-Butan (Section 2.5): Common name for butane Center of symmetry(Section 7.3): A point in the center of a CHaCHCh,cH structure located so that a line drawn from it to any element n-Butyl group(Section 2.10): The group CHa CH, CH, CH2-. of the structure, when extended an equal distance in the op sec-Butyl group (Section 2.10): The group posite direction, encounters an identical element. Benzene, for example, has a center of symmetry CH3CH_CHCH3 Chain reaction(Section 4. 18): Reaction mechanism in which a sequence of individual steps repeats itself many times, usu- tert-Butyl group(Section 2.10): The group(CH3)3C- ally because a reactive intermediate consumed in one step regenerated in a subsequent step. The halogenation of alkanes is a chain reaction proceeding via free-radical Cahn-ngold-Prelog notation(Section 7.6): System for spec- intermediates ifying absolute configuration as R or S on the basis of the Chair conformation (Section 3.5 ): The most stable conforma- order in which atoms or groups are attached to a stereogenic center. Groups are ranked in order of precedence according to rules based on atomic number Carbamate(Section 20. 17): An ester of carbamic acid Carbanion(Section 9.5): Anion in which the negative charge is Chemical shift (Section 13.4): A measure of how shielded the borne by carbon. An example is acetylide ion. Carbene(Section 14. 13): A neutral species in which one of the have different chemical shifts. and nuclei of the same atom carbon atoms is associated with six valence electrons have chemical shifts that are sensitive to their molecular Carbinolamine (Section 17.10): Compound of the type environment. In proton and carbon-13 NMR, chemica shifts are cited as 8, or parts per million(ppm), from the hy drogens or carbons, respectively, of tetramethylsilane HO-C-NR, Chiral(Section 7. 1): Term describing an object that is not su- perposable on its mirror image. Carbinolamines are formed by nucleophilic addition of an Chiral carbon atom ( Section 7. 2): a carbon that is bonded to amine to a carbonyl group and are intermediates in the for- four groups, all of which are different from one another. mation of imines and enamines Also called an asymmetric carbon atom. A more modern term Is stereogenIc center Carbocation (Section 4.9): Positive ion in which the charge re- Chiral center(Section 7.2): See stereogenic center sides on carbon. An example is tert-butyl cation, (CH3)C Carbocations are unstable species that, though they cannot Chlorohydrin(Section 6.17): A halohydrin in which the halo- normally be isolated, are believed to be intermediates in gen is chlorine(see halohydrin certain reactions Forward Main Menu TOC Study Guide Toc Student OLCMHHE WebsiteG-5 GLOSSARY Bond-line formula (Section 1.7): Formula in which connec￾tions between carbons are shown but individual carbons and hydrogens are not. The bond-line formula represents the compound (CH3)2CHCH2CH3. Boundary surface (Section 1.1): The surface that encloses the region where the probability of finding an electron is high (90—95%). Branched-chain carbohydrate (Section 25.12): Carbohydrate in which the main carbon chain bears a carbon substituent in place of a hydrogen or hydroxyl group. Bromohydrin (Section 6.17): A halohydrin in which the halo￾gen is bromine (see halohydrin). Bromonium ion (Section 6.16): A halonium ion in which the halogen is bromine (see halonium ion). Brønsted acid See acid. Brønsted base See base. Buckminsterfullerene (Chapter 11, box, “Carbon Clusters, Fullerenes, and Nanotubes”): Name given to the C60 cluster with structure resembling the geodesic domes of R. Buck￾minster Fuller; see front cover. n-Butane (Section 2.5): Common name for butane CH3CH2CH2CH3. n-Butyl group (Section 2.10): The group CH3CH2CH2CH2±. sec-Butyl group (Section 2.10): The group tert-Butyl group (Section 2.10): The group (CH3)3C±. Cahn—Ingold—Prelog notation (Section 7.6): System for spec￾ifying absolute configuration as R or S on the basis of the order in which atoms or groups are attached to a stereogenic center. Groups are ranked in order of precedence according to rules based on atomic number. Carbamate (Section 20.17): An ester of carbamic acid (H2NCO2H); a compound of the type H2NCO2R. Carbanion (Section 9.5): Anion in which the negative charge is borne by carbon. An example is acetylide ion. Carbene (Section 14.13): A neutral species in which one of the carbon atoms is associated with six valence electrons. Carbinolamine (Section 17.10): Compound of the type Carbinolamines are formed by nucleophilic addition of an amine to a carbonyl group and are intermediates in the for￾mation of imines and enamines. Carbocation (Section 4.9): Positive ion in which the charge re￾sides on carbon. An example is tert-butyl cation, (CH3)3C. Carbocations are unstable species that, though they cannot normally be isolated, are believed to be intermediates in certain reactions. W W HO±C±NR2 CH3CH2CHCH3 W Carboxylate ion (Section 19.5): The conjugate base of a car￾boxylic acid, an ion of the type RCO2 . Carboxylation (Section 19.11): In the preparation of a car￾boxylic acid, the reaction of a carbanion with carbon diox￾ide. Typically, the carbanion source is a Grignard reagent. Carboxylic acid (Sections 2.3 and 19.1): Compound of the type , also written as RCO2H. Carboxylic acid derivative (Section 20.1): Compound that yields a carboxylic acid on hydrolysis. Carboxylic acid de￾rivatives include acyl chlorides, anhydrides, esters, and amides. Carotenoids (Section 26.16): Naturally occurring tetrater￾penoid plant pigments. Cation (Section 1.2): Positively charged ion. Cellobiose (Section 25.14): A disaccharide in which two glu￾cose units are joined by a (1,4) linkage. Cellobiose is ob￾tained by the hydrolysis of cellulose. Cellulose (Section 25.15): A polysaccharide in which thou￾sands of glucose units are joined by (1,4) linkages. Center of symmetry (Section 7.3): A point in the center of a structure located so that a line drawn from it to any element of the structure, when extended an equal distance in the op￾posite direction, encounters an identical element. Benzene, for example, has a center of symmetry. Chain reaction (Section 4.18): Reaction mechanism in which a sequence of individual steps repeats itself many times, usu￾ally because a reactive intermediate consumed in one step is regenerated in a subsequent step. The halogenation of alkanes is a chain reaction proceeding via free-radical intermediates. Chair conformation (Section 3.5): The most stable conforma￾tion of cyclohexane: Chemical shift (Section 13.4): A measure of how shielded the nucleus of a particular atom is. Nuclei of different atoms have different chemical shifts, and nuclei of the same atom have chemical shifts that are sensitive to their molecular environment. In proton and carbon-13 NMR, chemical shifts are cited as , or parts per million (ppm), from the hy￾drogens or carbons, respectively, of tetramethylsilane. Chiral (Section 7.1): Term describing an object that is not su￾perposable on its mirror image. Chiral carbon atom (Section 7.2): A carbon that is bonded to four groups, all of which are different from one another. Also called an asymmetric carbon atom. A more modern term is stereogenic center. Chiral center (Section 7.2): See stereogenic center. Chlorohydrin (Section 6.17): A halohydrin in which the halo￾gen is chlorine (see halohydrin). RCOH O X RMgX RCO2H 1. CO2 2. H3O