Introduction to Alkenes and Alkynes
Alkynes and Alkenes and are hydrocarbons which correspondingly have carbon-carbon triple bond and carbon-carbon double bond functional groups. Molecular formulas of these unsaturated hydrocarbons demonstrate the multiple bonding of the functional groups:
Alkane R-CH2-CH2-R CnH2n+2 this is the maximum H/C ratio for a given number of carbon atoms.
Alkene R-CH=CH-R CnH2n Each double bond reduces the number of hydrogen atoms by 2.
Alkyne R-C≡C-R CnH2n-2 Each triple bond reduces the number of hydrogen atoms by 4.
In the Analysis of Molecular Formulas section as we discussed earlier, the hydrocarbon's molecular formula provides information about the possible structural types that it may represent. For an instance, consider compounds having the formula C5H8. The five-carbon alkane pentane's formula is C5H12 so the difference in hydrogen content is 4. This difference suggests such type of compounds may have a triple bond, two double bonds, a ring plus a double bond, or two rings. Some cases are demonstrated here, and there are at least fourteen others!
IUPAC Rules for the Alkene and Cycloalkene Nomenclature
1. The ene suffix (ending) indicates an alkene or cycloalkene.
2. The longest chain that is chosen for the root name must comprise both carbon atoms of the double bond.
3. The root chain must be numbered from the end nearest a double bond carbon atom. In the center of the chain if there is the double bond, the nearest substituent rule is used to determine the end where numbering starts.
4. The smaller of the two numbers designating the carbon atoms of the double bond is used as the double bond locator. If more than one double bond is presented the compound is named like a diene, triene or equivalent prefix indicating the number of double bonds and each double bond is assigned a locator number.
5. In cycloalkenes the double bond carbons are assigned ring locations #1 and #2. Which of the two is #1 may be determined by the nearest substituent rule.
6. Substituent groups containing double bonds are:
H2C=CH- Vinyl group
H2C=CH-CH2- Allyl group
IUPAC Rules for the Alkyne Nomenclature
1. The yne suffix (ending) point out an alkyne or cycloalkyne.
2. The longest chain that is chosen for the root name must include both carbon atoms of the triple bond.
3. The root chain must be numbered from the end nearest a triple bond carbon atom. In the center of the chain if there is the triple bond, the nearest substituent rule is employed to find out the end where numbering starts.
4. The smaller of the two numbers designating the carbon atoms of the triple bond is used as the triple bond locator.
5. Each must be assigned a locator number if several multiple bonds are present. Double bonds precede triple bonds in the IUPAC name, but chain is numbered from the end nearest a multiple bond, in spite of its nature.
6. Because the triple bond is linear, it can only be contained in rings larger than ten carbons. In the simple form of cycloalkynes the triple bond carbons are assigned ring locations #1 and #2. Which of the two is #1 may be determined by the nearest substituent rule.
7. Substituent groups containing triple bonds are:
HC≡C- the Ethynyl group
HC≡CH-CH2- the Propargyl group
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