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QuestionChemistry

The Diels-Alder reaction is a concerted reaction; this means: a) the reaction is highly endothermic b) the products contain rings c) the reaction folows Markovnikov's rule d) a mixture of endo and exo products are formed e) all bond making and bond breaking occurs simultaneously 2) Which of the following compounds absorbs the longest wavelength of UV-visible light? a) (E)-but- 2 -ene b) (Z)- 1,3 -hexadiene c) (E)- 1,3.5 -hexatriene d) (Z)-but-ene e) hex- 1 -ene
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Step 1:
I'll solve this problem step by step, focusing on the UV-visible light absorption characteristics of these compounds.

Step 2:
: Understand the Factors Affecting UV-Visible Light Absorption

The wavelength of UV-visible light absorption depends on the conjugation and electron delocalization in the molecule. Key factors include: - Number of conjugated double bonds - Geometry of the conjugated system - Electron density in the π system

Step 3:
: Analyze the Conjugation in Each Molecule

e) Hex-1-ene: $$CH_{2}=CH-CH_{2}-CH_{2}-CH_{2}-CH_{3}
- 1 double bond - Limited conjugation - Minimal electron delocalization - 2 conjugated double bonds - Allows more electron delocalization - Potential for longer wavelength absorption - 3 conjugated double bonds - Extensive electron delocalization - Longest potential conjugation - Identical to (E)-but- 2 -ene - 1 double bond - Limited conjugation - 1 isolated double bond - No conjugation - Shortest wavelength absorption

Step 4:
: Determine the Wavelength of Absorption

The more conjugated the system, the longer the wavelength of absorbed light. - Ranking from longest to shortest wavelength:

Step 5:
(E)- 1,3,5 -hexatriene

Step 6:
(Z)- 1,3 -hexadiene

Step 7:
(Z)-but- 2 -ene

Step 8:
(E)-but- 2 -ene

Step 9:

Hex- 1 -ene

Final Answer

c) (E)- 1,3,5 -hexatriene will absorb the longest wavelength of UV-visible light due to its extensive conjugation of three double bonds.