Nomenclature & Conformations of Alkanes & Cycloalkanes
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1 Chapter 4 Nomenclature & Conformations of Alkanes & Cycloalkanes Ch. 4-1
2 1. Introduction to Alkanes & Cycloalkanes Alkanes and cycloalkanes are hydrocarbons in which all the carboncarbon (C C) bonds are single bonds ydrocarbons that contain C C: Alkenes ydrocarbons that contain C C: Alkynes Ch. 4-2
3 Alkanes: C n 2n+2 e.g hexane (C 6 14 ) Cycloalkanes: C n 2n e.g. cyclohexane (C 6 12 ) Ch. 4-3
4 1A. Sources of Alkanes: Petroleum Petroleum is the primary source of alkanes. It is a complex mixture of mostly alkanes and aromatic hydrocarbons with small amounts of oxygen-, nitrogen-, and sulfurcontaining compounds Ch. 4-4
5 Petroleum refining Distillation is the first step in refining petroleum. Its components are separated based on different volatility More than 500 different compounds are contained in petroleum distillates boiling below 200 o C Ch. 4-5
6 Petroleum refining (Cont d) The fractions taken contain a mixture of alkanes of similar boiling points Mixture of alkanes can be used as fuels, solvents, and lubricants Ch. 4-6
7 Gasoline The demand of gasoline is much greater than that supplied by the gasoline fraction of petroleum Converting hydrocarbons from other fractions of petroleum into gasoline by catalytic cracking mixture of alkanes (C 12 and higher) catalysts ~ 500 o C highly branched hydrocarbons (C 5 - C 10 ) Ch. 4-7
8 Gasoline (Cont d) C 3 C 3 C 3 C C 2 C C 3 C 3 2,2,4-Trimethylpentane (isooctane) (C ) Isooctane burns very smoothly (without knocking) in internal combustion engines and is used as one of the standards by which the octane rating of gasoline is established Ch. 4-8
9 Gasoline (Cont d) isooctane heptane "octane rating" e.g. a gasoline of a mixture: 87% isooctane and 13% heptane Rated as 87-octane gasoline Ch. 4-9
10 Typical Fractions Obtained by Distillation of Petroleum Boiling Range of Fraction ( o C) # of Carbon Atoms per Molecule Use Below 20 C 1 C 4 Natural gas, bottled gas, petrochemicals C 5 C 6 Petroleum ether, solvents C 6 C 7 Ligroin, solvents C 5 C 10 Gasoline (straightrun gasoline) C 12 C 18 Kerosene and jet fuel Ch. 4-10
11 Typical Fractions Obtained by Distillation of Petroleum (Cont d) Boiling Range of Fraction ( o C) # of Carbon Atoms per Molecule Use C 12 and higher Gas oil, fuel oil, and diesel oil Nonvolatile liquids C 20 and higher Refined mineral oil, lubricating oil, and grease Nonvolatile solids C 20 and higher Paraffin wax, asphalt, and tar Ch. 4-11
12 2. Shapes of Alkanes All carbon atoms in alkanes and cycloalkanes are sp 3 hybridized, and they all have a tetrahedral geometry Even straight-chain alkanes are not straight. They have a zigzag geometry Ch. 4-12
13 Straight-chain (unbranched) alkanes Butane Pentane C 3 C 2 C 2 C 3 C 3 C 2 C 2 C 2 C 3 Ch. 4-13
14 Branched-chain alkanes Isobutane Neopentane C 3 C 3 C 3 C 3 C C 3 C C 3 C 3 Ch. 4-14
15 Butane and isobutane have the same molecular formula (C 4 10 ) but different bond connectivities. Such compounds are called constitutional isomers Butane Isobutane Ch. 4-15
16 C 4 and higher alkanes exist as constitutional isomers. The number of constitutional isomers increases rapidly with the carbon number Molecular Formula # of Possible Const. Isomers Molecular Formula # of Possible Const. Isomers C C C C C C ,319 C C ,481,801,147,341 C Ch. 4-16
17 Constitutional isomers usually have different physical properties exane Isomers (C 6 14 ) Formula M.P. ( o C) B.P. ( o C) Density (g/ml) Refractive Index Ch. 4-17
18 3. IUPAC Nomenclature of Alkanes, Alkyl alides, & Alcohols One of the most commonly used nomenclature systems that we use today is based on the system and rules developed by the International Union of Pure and Applied Chemistry (IUPAC) Fundamental Principle: Each different compound shall have a unique name Ch. 4-18
19 Although the IUPAC naming system is now widely accepted among chemists, common names (trivial names) of some compounds are still widely used by chemists and in commerce. Thus, learning some of the common names of frequently used chemicals and compounds is still important Ch. 4-19
20 The ending for all the names of alkanes is ane The names of most alkanes stem from Greek and Latin one two three four five meth- eth- prop- but- pent- Ch. 4-20
21 Unbranched alkanes Name Structure Name Structure Methane C 4 exane C 3 (C 2 ) 4 C 3 Ethane C 3 C 3 eptane C 3 (C 2 ) 5 C 3 Propane C 3 C 2 C 3 Octane C 3 (C 2 ) 6 C 3 Butane C 3 C 2 C 2 C 3 Nonane C 3 (C 2 ) 7 C 3 Pentane C 3 (C 2 ) 3 C 3 Decane C 3 (C 2 ) 8 C 3 Ch. 4-21
22 3A. Nomenclature of Unbranched Alkyl Groups Alkyl group Removal of one hydrogen atom from an alkane Ch. 4-22
23 Alkyl group (Cont d) For an unbranched alkane, the hydrogen atom that is removed is a terminal hydrogen atom C 3 C 3 C 2 C 3 C 2 C 2 Methane Ethane Propane C 3 C 3 C 2 C 3 C 2 C 2 Methyl Ethyl Propyl (Me) (Et) (Pr) Ch. 4-23
24 3B. Nomenclature of Branched-Chain Alkanes Rule 1. Use the longest continuous carbon chain as parent name C 3 C 2 C 2 C 2 CC 3 1C 3 (3-Methylheptane) 2 C C 3 C 2 C 2 C 2 CC 3 NOT C 2 C 3 (2-Ethylhexane) Ch. 4-24
25 Rule (Cont d) 2. Use the lowest number of the substituent 3. Use the number obtained by Rule 2 to designate the location of the substituent C 3 C 2 C 2 C 2 CC 3 1C 3 (3-Methylheptane) 2 C C 3 C 2 C 2 C 2 CC 3 NOT 7C 3 (5-Methylheptane) 6 C 2 Ch. 4-25
26 Rule (Cont d) 4. For two or more substituents, use the lowest possible individual numbers of the parent chain The substitutents should be listed alphabetically. In deciding alphabetical order, disregard multiplying prefix, such as di, tri etc. Ch. 4-26
27 Rule (Cont d) (6-Ethyl-2-methyloctane) NOT NOT (3-Ethyl-7-methyloctane) (2-Methyl-6-ethyloctane) Ch. 4-27
28 Rule (Cont d) 5. When two substituents are present on the same carbon, use that number twice (4-Ethyl-4-methyloctane) Ch. 4-28
29 Rule (Cont d) 6. For identical substituents, use prefixes di-, tri-, tetra- and so on (2,4-Dimethylhexane) NOT (2,4,5-Trimethylheptane) NOT (3,5-Dimethylhexane) (3,4,6-Trimethylheptane) Ch. 4-29
30 Rule (Cont d) 7. When two chains of equal length compete for selection as parent chain, choose the chain with the greater number of substituents NOT 6 (2,3,5-Trimethyl- 4-propylheptane) 7 (only three substituents) Ch. 4-30
31 Rule (Cont d) 8. When branching first occurs at an equal distance from either end of the longest chain, choose the name that gives the lower number at the first point of difference NOT (2,3,5-Trimethylhexane) (2,4,5-Trimethylhexane) Ch. 4-31
32 Example 1 Find the longest chain as parent or Ch. 4-32
33 Example 1 (Cont d) Use the lowest numbering for substituents instead of Substituents: two methyl groups dimethyl Ch. 4-33
34 Example 1 (Cont d) Complete name (3,4-Dimethylheptane) Ch. 4-34
35 Example 2 Ch. 4-35
36 Example 2 (Cont d) Find the longest chain as parent 6-carbon chain 8-carbon chain 8-carbon chain Ch. 4-36
37 Example 2 (Cont d) Find the longest chain as parent 9-carbon chain (correct!) Nonane as parent Ch. 4-37
38 Example 2 (Cont d) Use the lowest numbering for substituents instead of (3,4,7) (3,6,7) Ch. 4-38
39 Example 2 (Cont d) Substituents 3,7-dimethyl 4-ethyl Ch. 4-39
40 Example 2 (Cont d) Substituents in alphabetical order Ethyl before dimethyl (recall Rule 4 disregard di ) Complete name (4-Ethyl-3,7-dimethylnonane) Ch. 4-40
41 3C. Nomenclature of Branched Alkyl Groups For alkanes with more than two carbon atoms, more than one derived alkyl group is possible Three-carbon groups Propyl Isopropyl (or 1-methylethyl) Ch. 4-41
42 Four-carbon groups Butyl Isobutyl sec-butyl (1-methylpropyl) tert-butyl (or 1,1-dimethylethyl) Ch. 4-42
43 A neopentyl group neopentyl (2,2,-dimethylpropyl) Ch. 4-43
44 Example 1 Ch. 4-44
45 Example 1 (Cont d) Find the longest chain as parent (a) (b) 6-carbon chain 7-carbon chain (c) (d) 8-carbon chain 9-carbon chain Ch. 4-45
46 Example 1 (Cont d) Find the longest chain as parent (d) Nonane as parent or Ch. 4-46
47 Example 1 (Cont d) Use the lowest numbering for substituents or ,6 4,5 (lower numbering) Use 4,5 Ch. 4-47
48 Example 1 (Cont d) Substituents Isopropyl tert-butyl isopropyl and 5-tert-butyl Ch. 4-48
49 Example 1 (Cont d) Alphabetical order of substituents tert-butyl before isopropyl Complete name tert-Butyl-4-isopropylnonane Ch. 4-49
50 Example 2 Ch. 4-50
51 Example 2 (Cont d) (a) Find the longest chain as parent (b) 8-carbon chain 9-carbon chain (c) Octane as parent 10-carbon chain Ch. 4-51
52 Example 2 (Cont d) or Ch. 4-52
53 Example 2 (Cont d) Use the lowest numbering for substituents 5, or 5,6 Determined using the next Rules Ch. 4-53
54 Example 2 (Cont d) Substituents sec-butyl Neopentyl But is it 5-sec-butyl and 6-neopentyl or 5-neopentyl and 6-sec-butyl? Ch. 4-54
55 Example 2 (Cont d) Since sec-butyl takes precedence over neopentyl 5-sec-butyl and 6-neopentyl Complete name sec-Butyl-6-neopentyldecane Ch. 4-55
56 3D. Classification of ydrogen Atoms 1 o hydrogen atoms C 3 C 3 C C 2 C 3 3 o hydrogen atoms 2 o hydrogen atoms Ch. 4-56
57 3E. Nomenclature of Alkyl alides Rules alogens are treated as substituents (as prefix) F: fluoro Br: bromo Cl: chloro I: iodo Similar rules as alkyl substituents Ch. 4-57
58 Examples Cl Br 2-Bromo-1-chlorobutane Cl Cl C 3 1,4-Dichloro-3-methylhexane Ch. 4-58
59 3F. Nomenclature of Alcohols IUPAC substitutive nomenclature: a name may have as many as four features Locants, prefixes, parent compound, and suffixes O Methyl-1-hexanol Ch. 4-59
60 Rules Select the longest continuous carbon chain to which the hydroxyl is directly attached. Change the name of the alkane corresponding to this chain by dropping the final e and adding the suffix ol Number the longest continuous carbon chain so as to give the carbon atom bearing the hydroxyl group the lower number. Indicate the position of the hydroxyl group by using this number as a locant Ch. 4-60
61 Examples O Propanol (isopropyl alcohol) 4 O O O 1,2,3-Butanetriol O 4-Methyl-1-pentanol (or 4-Methylpentan-1-ol) (NOT 2-Methyl-5-pentanol) Ch. 4-61
62 Example 4 O Ch. 4-62
63 Example 4 (Cont d) Find the longest chain as parent O or O Longest chain but does not contain the O group 7-carbon chain containing the O group eptane as parent Ch. 4-63
64 Example 4 (Cont d) Use the lowest numbering for the carbon bearing the O group or O 2,3 (lower numbering) O 5,6 Use 2,3 Ch. 4-64
65 Example 4 (Cont d) Parent and suffix 2-eptanol Substituents Propyl O Complete name 3-Propyl-2-heptanol Ch. 4-65
66 4. ow to Name Cycloalkanes 4A. Monocyclic Compounds Cycloalkanes with only one ring Attach the prefix cyclo- 2 C C 2 C 2 = Cyclopropane 2 C C 2 = 2 C C 2 C2 Cyclopentane Ch. 4-66
67 Substituted cycloalkanes Isopropylcyclopropane Methylcyclopropane tert-butylcyclopentane Ch. 4-67
68 Example Ethyl-3-methylcyclopentane NOT NOT Ethyl-4-methylcyclopentane 3-Ethyl-1-methylcyclopentane Ch. 4-68
69 Example 2 Br Bromo-2-ethyl-1-methyl cyclohexane NOT Br Bromo-3-ethyl-4-methyl cyclohexane (lowest numbers of substituents are 1,2,4 not 1,3,4) Ch. 4-69
70 Example O 4-Ethyl-3-methyl cyclohexanol NOT O 1-Ethyl-2-methyl cyclohexan-4-ol (the carbon bearing the O should have the lowest numbering, even though 1,2,4 is lower than 1,3,4) Ch. 4-70
71 Cycloalkylalkanes When a single ring system is attached to a single chain with a greater number of carbon atoms 1-Cyclobutylpentane When more than one ring system is attached to a single chain 1,3-Dicyclohexylpropane Ch. 4-71
72 4B. Bicyclic Compounds Bicycloalkanes Alkanes containing two fused or bridged rings Total # of carbons = 7 Bicycloheptane Bridgehead Ch. 4-72
73 Example (Cont d) Between the two bridgeheads Two-carbon bridge on the left Two-carbon bridge on the right One-carbon bridge in the middle Complete name Bicyclo[2.2.1]heptane Ch. 4-73
74 Other examples Methylbicyclo[4.3.0]nonane Isopropylbicyclo[2.2.2]octane Ch. 4-74
75 5. Nomenclature of Alkenes & Cycloalkenes Rule 1. Select the longest chain that contains C=C as the parent name and change the name ending of the alkane of identical length from ane to ene Ch. 4-75
76 Rule 2. Number the chain so as to include both carbon atoms of C=C, and begin numbering at the end of the chain nearer C=C. Assign the location of C=C by using the number of the first atom of C=C as the prefix. The locant for the alkene suffix may precede the parent name or be placed immediately before the suffix Ch. 4-76
77 Examples C 2 CC 2 C 3 1-Butene (not 3-Butene) C 3 C CC 2 C 2 C 3 2-exene (not 4-exene) Ch. 4-77
78 Rule 3. Indicate the locations of the substituent groups by the numbers of the carbon atoms to which they are attached Examples Methyl-2-butene (not 3-Methyl-2-butene) 3 4 Ch. 4-78
79 Examples (Cont d) ,5-Dimethyl-2-hexene NOT ,5-Dimethyl-4-hexene Ch. 4-79
80 Rule 4. Number substituted cycloalkenes in the way that gives the carbon atoms of C=C the 1 and 2 positions and that also gives the substituent groups the lower numbers at the first point of difference Ch. 4-80
81 Example ,5-Dimethylcyclohexene 3 NOT ,6-Dimethylcyclohexene 6 Ch. 4-81
82 Rule 5. Name compounds containing a C=C and an alcohol group as alkenols (or cycloalkenols) and give the alcohol carbon the lower number Examples O 4 2-Methyl-2-cyclohexen-1-ol (or 2-Methylcyclohex-2-en-1-ol) 3 Ch. 4-82
83 Examples (Cont d) O 4-Methyl-3-penten-2-ol (or 4-Methylpent-3-en-2-ol) 2 1 Ch. 4-83
84 Rule 6. Vinyl group & allyl group Vinyl group Allyl group ethenyl prop-2-en-1-yl O Ethenylcyclopropane (or Vinylcyclopropane) (Prop-2-en-1-yl) cyclohexan-1-ol (or 3-Allylcyclohexanol) Ch. 4-84
85 Rule 7. Cis vs. Trans Cis: two identical or substantial groups on the same side of C=C Trans: two identical or substantial groups on the opposite side of C=C Cl Cl Cl Cl cis-1,2-dichloroethene trans-1,2-dichloroethene Ch. 4-85
86 Example Ch. 4-86
87 Example (Cont d) (a) (b) 1 (c) (d) Ch. 4-87
88 Example (Cont d) Complete name tert-Butyl-2-methyl-1-heptene Ch. 4-88
89 6. Nomenclature of Alkynes Alkynes are named in much the same way as alkenes, but ending name with yne instead of ene Examples Br 2-eptyne 4-Bromo-1-butyne Ch. 4-89
90 Examples (Cont d) I Br Bromo-7-iodo-6-isopropyl-8-methyl-3-decyne Ch. 4-90
91 O group has priority over C C O 3-Butyn-1-ol NOT O O Methyl-5-octyn-2-ol O NOT Ch. 4-91
92 7. Physical Properties of Alkanes & Cycloalkanes Boiling points & melting points Ch. 4-92
93 C 6 14 Isomer Boiling Point ( o C) Ch. 4-93
94 Physical Constants of Cycloalkanes # of C Refractive Atoms Name bp ( o C) mp ( o C) Density Index 3 Cyclopropane Cyclobutane Cyclopentane Cyclohexane Cycloheptane Cyclooctane Ch. 4-94
95 8. Sigma Bonds & Bond Rotation Two groups bonded by a single bond can undergo rotation about that bond with respect to each other Conformations temporary molecular shapes result from a rotation about a single bond Conformer each possible structure of conformation Conformational analysis analysis of energy changes occur as a molecule undergoes rotations about single bonds Ch. 4-95
96 8A. Newman Projections Me Sawhorse formula Look from this direction Cl Et O Me Cl Et O front carbon back carbon combine Me Cl Et O Newman Projection Ch. 4-96
97 8B. ow to Do a Conformational Analysis Look from this direction φ 2 = 180 o a c b φ 1 = 60 o staggered confirmation of ethane Ch. 4-97
98 180 o C 3 60 o C 3 C 3 0 o C 3 C 3 C 3 anti gauche eclipsed Ch. 4-98
99 Look from this direction φ = 0 o eclipsed confirmation of ethane Ch. 4-99
100 Ch
101 9. Conformational Analysis of Butane Me Me Me Sawhorse formula Me New Projection formula Ch
102 C 3 C 3 C 3 C 3 C 3 anti conformer (I) (lowest energy) C 3 eclipsed conformer (II) gauche conformer (III) = C 3 on front carbon rotates 60 o clockwise C 3 C 3 C 3 C 3 3 C C 3 eclipsed conformer (VI) gauche conformer (V) eclipsed conformer (IV) (highest energy) Ch
103 Ch
104 10. The Relative Stabilities of Cycloalkanes: Ring Strain Cycloalkanes do not have the same relative stability due to ring strain Ring strain comprises: Angle strain result of deviation from ideal bond angles caused by inherent structural constraints Torsional strain result of dispersion forces that cannot be relieved due to restricted conformational mobility Ch
105 10A. Cyclopropane θ sp 3 hybridized carbon (normal tetrahedral bond angle is o ) Internal bond angle (θ) ~60 o (~49.5 o deviated from the ideal tetrahedral angle) Ch
106 Ch
107 10B. Cyclobutane θ Internal bond angle (θ) ~88 o (~21 o deviated from the normal o tetrahedral angle) Ch
108 Cyclobutane ring is not planar but is slightly folded. If cyclobutane ring were planar, the angle strain would be somewhat less (the internal angles would be 90 o instead of 88 o ), but torsional strain would be considerably larger because all eight C bonds would be eclipsed Ch
109 10C. Cyclopentane If cyclopentane were planar, θ ~108 o, very close to the normal tetrahedral angle of o owever, planarity would introduce considerable torsional strain (i.e. 10 C bonds eclipsed) Therefore cyclopentane has a slightly bent conformation Ch
110 11. Conformations of Cyclohexane: The Chair & the Boat 3D (chair form) (boat form) (more stable) (less stable) Ch
111 The boat conformer of cyclohexane is less stable (higher energy) than the chair form due to Eclipsed conformation 1,4-flagpole interactions 1 4 (eclipsed) Ch
112 (twist boat) The twist boat conformation has a lower energy than the pure boat conformation, but is not as stable as the chair conformation Ch
113 Energy diagram Ch
114 12. Substituted Cyclohexanes: Axial & Equatorial ydrogen Atoms Equatorial hydrogen atoms in chair form Axial hydrogen atoms in chair form Ch
115 Substituted cyclohexane Two different chair forms G G G (equatorial G) (more stable) (axial G) (less stable) G Ch
116 The chair conformation with axial G is less stable due to 1,3-diaxial interaction 1,3-diaxial interaction 3 G 1 The larger the G group, the more severe the 1,3-diaxial interaction and shifting the equilibrium from the axial- G chair form to the equatorial-g chair form Ch
117 G (equatorial) (axial) G At 25 o C G % of Equatorial % of Axial F C i Pr 97 3 t Bu > < 0.01 Ch
118 13. Disubstituted Cycloalkanes Cis-Trans Isomerism C 3 C 3 C 3 cis-1,2-dimethyl cyclopropane C 3 trans-1,2-dimethyl cyclopropane Cl Cl Cl cis-1,2-dichloro cyclobutane Cl trans-1,2-dichloro cyclobutane Ch
119 13A.Cis-Trans Isomerism & Conformation Structures of Cyclohexanes Trans-1,4-Disubstituted Cyclohexanes C 3 C 3 ring flip 3 C C 3 trans-diaxial trans-diequatorial Ch
120 Upper bond 3 C C 3 trans-dimethyl cyclohexane Lower bond Upper-lower bonds means the groups are trans Ch
121 Cis-1,4-Disubstituted Cyclohexanes 3 C C 3 chair-chair C 3 ring flip C 3 Equatorial-axial Axial-equatorial Ch
122 Cis-1-tert-Butyl-4-methylcyclohexane 3 C 3 C C 3 C 3 ring flip 3 C 3 C C3 C 3 (more stable because large group is equatorial) (less stable because large group is axial) Ch
123 Trans-1,3-Disubstituted Cyclohexanes (ax) (eq) 3 C C 3 (ax) ring flip C 3 C 3 (eq) trans-1,3-dimethylcyclohexane Ch
124 Trans-1-tert-Butyl-3-methylcyclohexane 3 C 3 C C 3 C 3 ring flip 3 C 3 C C3 C 3 (more stable because large group is equatorial) (less stable because large group is axial) Ch
125 Cis-1,3-Disubstituted Cyclohexanes C 3 ring flip C 3 C 3 C 3 (more stable) (less stable) Ch
126 Trans-1,2-Disubstituted Cyclohexanes (eq) C 3 C 3 (eq) diequatorial (much more stable) ring flip (ax) C 3 (ax) C 3 diaxial (much less stable) trans-1,2-dimethylcyclohexane Ch
127 Cis-1,2-Disubstituted Cyclohexane (ax) C 3 C 3 (eq) (equatorial-axial) ring flip (ax) C 3 C 3 (eq) (axial-equatorial) cis-1,2-dimethylcyclohexane (equal energy and equally populated conformations) Ch
128 14. Bicyclic & Polycyclic Alkanes Decalin (Bicyclo[4.4.0]decane) cis-decalin trans-decalin Ch
129 Adamantane Cubane Prismane C 60 (Buckminsterfullerene) Ch
130 16. Synthesis of Alkanes and Cycloalkanes 16A.ydrogenation of Alkenes & Alkynes 2 Pt, Pd or Ni solvent heat and pressure C C 2 2 Pt, Pd or Ni solvent heat and pressure C C Ch
131 Examples Ni + 2 EtO 25 o C, 50 atm. Pd + 2 EtO 25 o C, 1 atm. Pd EtOAc o 2 C, 1 atm. Ch
132 17. ow to Gain Structural Information from Molecular Formulas & Index of ydrogen Deficiency Index of hydrogen deficiency (ID) The difference in the number of pairs of hydrogen atoms between the compound under study and an acyclic alkane having the same number of carbons Also known as degree of unsaturation or double-bond equivalence (DBE) Ch
133 Index of hydrogen deficiency (Cont d) Saturated acyclic alkanes: C n 2n+2 Each double bond on ring: 2 hydrogens less Each double bond on ring provides one unit of hydrogen deficiency Ch
134 e.g. exane: C 6 14 and C exene Cycloheane Index of hydrogen deficiency (ID) = C 6 14 C = one pair of 2 = 1 Ch
135 Examples ID = 2 ID = 3 ID = 2 ID = 4 Ch
136 16A.Compounds Containing alogen, Oxygen, or Nitrogen For compounds containing alogen count halogen atoms as though they were hydrogen atoms Oxygen ignore oxygen atoms and calculate ID from the remainder of the formula Nitrogen subtract one hydrogen for each nitrogen atom and ignore nitrogen atoms Ch
137 Example 1: ID of C 4 6 Cl 2 Count Cl as C 4 6 Cl 2 C 4 8 A C 4 acyclic alkane: C 4 2(4)+2 = C 4 10 C 4 10 C ID of C 4 6 Cl 2 = one pair of 2 = 1 Cl Possible structures Cl Cl or Cl... etc. or Cl Cl Ch
138 Example 2: ID of C 5 8 O Ignore oxygen C 5 8 O C 5 8 A C 5 acyclic alkane: C 5 2(5)+2 = C 5 12 C 5 12 C ID of C 4 6 Cl 2 = two pair of 2 = 2 Possible structures O or O or... etc. O Ch
139 Example 3: ID of C 5 7 N Subtract 1 for each N C 5 7 N C 5 6 A C 5 acyclic alkane: C 5 2(5)+2 = C 5 12 C 5 12 C ID of C 4 6 Cl 2 = three pair of 2 = 3 Possible structures N C 3 or C N... etc. Ch
140 END OF CAPTER 4 Ch
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