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Ch.23 - Organic and Biological Chemistry
Chapter 23, Problem 6

How many dienes (compounds with two double bonds) are there with the formula C5H8? Draw as many structures as you can.

Verified step by step guidance
1
Step 1: Understand the molecular formula C5H8, which indicates a hydrocarbon with 5 carbon atoms and 8 hydrogen atoms. The presence of two double bonds classifies it as a diene.
Step 2: Calculate the degree of unsaturation using the formula: Degree of Unsaturation = (2C + 2 + N - H - X) / 2, where C is the number of carbons, N is the number of nitrogens, H is the number of hydrogens, and X is the number of halogens. For C5H8, this simplifies to (2*5 + 2 - 8) / 2.
Step 3: Recognize that the degree of unsaturation indicates the number of rings and/or multiple bonds. For C5H8, the degree of unsaturation is 2, which can be satisfied by two double bonds.
Step 4: Begin drawing possible structures by arranging the carbon atoms in a linear or branched chain and adding double bonds. Ensure that each carbon atom forms four bonds in total.
Step 5: Verify each structure by counting the total number of carbon and hydrogen atoms to ensure they match the molecular formula C5H8, and confirm that each structure contains exactly two double bonds.