MWF_6 - Organic Lecture Series CH 310/318 M Textbook...

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Organic Lecture Series 1 CH 310/318 M LECTURE 6 Textbook Assignment: Chapter 3 Today’s Topics: Cycloalkanes Cycloalkanes -conformers conformers Notice & Announcements: Organic Lecture Series 2 Cyclopentane Cyclopentane – Puckering from planar cyclopentane reduces torsional strain, but increases angle stain. – The conformation of minimum energy is a puckered “envelope” conformation. – Strain energy is about 42 kJ (6.5 kcal)/mol.
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Organic Lecture Series 3 Cyclohexane Cyclohexane • Chair conformation: Chair conformation: The most stable puckered conformation of a cyclohexane ring. – all bond C-C-C bond angles are 110.9°. all bonds on adjacent carbons are staggered. Organic Lecture Series 4 • In a chair conformation, six H are equatorial and six are axial. Cyclohexane Cyclohexane
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Organic Lecture Series 5 • For cyclohexane, there are two equivalent chair conformations. – all C-H bonds equatorial in one chair are axial in the alternative chair and vice versa. Cyclohexane Cyclohexane Organic Lecture Series 6 • Boat conformation: Boat conformation: A puckered conformation of a cyclohexane ring in which carbons 1 and 4 are bent toward each other. – there are four sets of eclipsed C-H interactions and one flagpole interaction (flagpole H green).
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MWF_6 - Organic Lecture Series CH 310/318 M Textbook...

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