Prefix Root Suffix. Alkanes & Cycloalkanes. Hydrocarbon composed only of. Saturated hydrocarbon contains only
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1 Alkanes & ycloalkanes ydrocarbon composed only of Saturated hydrocarbon contains only Unsaturated hydrocarbon contains at least one Alkene Alkyne Aromatic Alkane saturated hydrocarbon General formula: First 10 straight-chained n- alkanes: Name Molecular ondensed Structure Formula ( 2 ) ( 2 ) ( 2 ) ( 2 ) ( 2 ) ( 2 ) 8 3 Naming: IUPA International Union of Pure and Applied hemistry Prefix Root Suffix hpt. 3 Notes - 1
2 Rules: 1. Find the longest continuous chain of carbons. Alkanes root & suffix *For more than one longest chain 2. Identify all side groups Names of Straight hain Side Groups hain Name hain Name 3-3 ( 2 ) ( 2 ) ( 2 ) ( 2 ) ( 2 ) Branched hain Side Groups Name ondensed Formula Structure ( 3 ) ( 3 )- ( 3 ) ( 3 ) 3 - hpt. 3 Notes - 2
3 alogen and Other Noncarbon Side Groups Name Group Name Group F- I- l- NO 2 - Br- *Side groups ordered *For more than one of a given side group *Number carbons in chain For equivalent number sets *omplex substituents: longest continuous chain rest = #1 is offset by Examples: Br l NO 2 Br Br hpt. 3 Notes - 3
4 Structure from Name: *Parent compound first then prefixes Examples: 2-methylbutane 2,2,4,4-tetraiodopentane 3-ethylhexane 3-ethyl-2-methyl-4-propylheptane Physical properties: Soluble in nonpolar solvents Density Boiling pts. Melting pts. Branched alkanes versus straight chained Boiling pts low in comparison with other types of compounds Only have Ex: methane kerosene paraffin wax hpt. 3 Notes - 4
5 onstitutional Isomers compounds with the same molecular formula but different arrangement of atoms (a.k.a. isomers) Ex: 4 10 Butane bp = -0.4 isobutane bp = Ex: 5 12 three constitutional isomers Pentane bp = 36.1 Isopentane bp = 27.8 Neopentane bp = 9.5 To test if isomers are truly different lassification of arbons: Primary (1 ) bonded to 3 Secondary (2 ) bonded to Tertiary (3 ) bonded to 3 3 Quarternary (4 ) bonded to 2,2,4-trimethylpentane hpt. 3 Notes - 5
6 ycloalkanes saturated hydrocarbons General formula: (x = # of rings) Ex: Or Properties: Nonpolar, relatively inert Bp & mp depends Bp & mp similar to Naming: **If ring is large/more substituted than straight chain, name as cycloalkane: 1. Parent name = cyclo + alkane name 2. If 1 substituent 3. If 2 substituents 4. If >2 substituents 5. As substituent: name of ring e + yl ex: Ex: ( 3 ) 2 3 l Reactions: 1. ombustion Ex: combustion of butane hpt. 3 Notes - 6
7 2. racking Petroleum refining: onformation 3-D arrangement due to Ex: ethane onformations of alkanes & cycloalkanes Newman Projection view along axis Ex: ethane Staggered Eclipsed Skewed Potential energy diagram: hpt. 3 Notes - 7
8 onformations of butane: Totally eclipsed gauche eclipsed anti Intramolecular strain: 1. Nonbonded interaction strain Torsional strain **Larger group 2. Steric hindrance onformations of cycloalkanes: cyclopentanes & cyclohexanes **5 & 6-membered rings most common Why? Ring strain: arbons are hybridized; angles If angle different yclobutane: bond angles compressed from to ydrogens are eclipsed angle strain Ring strain + eat of combustion: energy released during combustion (measure of kcal/mol (typical) ycloalkane Bond Angle Increased heat of combustion yclopropane kcal yclobutane kcal yclopentane kcal yclohexane kcal hpt. 3 Notes - 8
9 yclopentane: conformation is To reduce: & Observed angles: yclohexane: 2 main conformations hair* *angles are * s are Boat Positions of groups bonded to ring: Axial Equatorial onformational changes: hair hair hpt. 3 Notes - 9
10 Interconvert at room temperature Axial equatorial Major form minimal bulky group Ex: Show the two conformations of ethylcyclohexane; which is more stable? is-trans isomers: 1. same molecular formula 2. same order of attachment 3. different arrangement in space due to: is Trans is-1,2-dimethylcyclobutane Trans-1,2-dimethylcyclobutane hpt. 3 Notes - 10
11 Draw the two chair conformations of: cis-1,2-dimethylcyclohexane: Draw the most stable conformer (s) for trans-1-ethyl-4-isopropylcyclohexane: Read & note: Sect. 3-5, 3-16 Suggested problems: 33 (a,c), 34 (evens), 37 (evens), 38, 40, 42, 43 (a,b), 44 (evens) hpt. 3 Notes - 11
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Spectroscopy Beauchamp 1 Basics of Mass Spectroscopy The roots of mass spectroscopy (MS) trace back to the early part of the 20th century. In 1911 J.J. Thomson used a primitive form of MS to prove the