{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

SCAN0006 - Practice 8 — Alkane Stereochemistry 1 3(a CH3...

Info icon This preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Practice 8 — Alkane Stereochemistry 1) 3) (a ) CH3 t—Bu Me , . H3C Cl (0') CN (8) OH 002H HO (Z7 \CN Et : % / , Et For the molecules below: a) Provide a 3 dimensional structure at the indicated carbons. b) Draw the Newman projection for your structure indicating the direction of sight with an arrow. 0) Draw the Newman projection for the most stable conformation. Draw a 3D structure for your Newman structure indicating the direction of sight with an arrow. d) Draw the Newman projection for the least stable conformation. Draw a 3D structure for your Newman structure indicating the direction of sight with an arrow. e) For (i) and (ii), calculate the energy difference between the most and least stable conformations. For (iii), calculate the strain caused by a C—CH3 bond eclipsed with C—OH since the barrier to rotation is 17 kJ/mol. For (iv), calculate the strain in the least stable conformation. a) Draw chair cyclohexane 20 times. Compare to text. Cross out incorrect ones. b) Draw chair cyclohexane 20 more times and put in all the axial bonds on each. Compare to text. c) Draw chair cyclohexane 20 more times and put in all the equatorial bonds on each. Compare'to text d) Draw a 1,2,3-tribromocyclohexane where all bromines are in equatorial positions. 9) Draw a 1,2,3-tribromocyclohexane where all bromines are in an axial positions. Draw both possible chair conformations for the indicated cyclohexane: ‘ ’ a) b) C) d) trans—1-chloro—2-methylcyclohexane. e) trans-1-chloro-4-methylcyclohexane. sis—1—chloro—2—methylcyclohexane. f) cis-1-chIoro-4-methylcyclohexane. trans-1—chloro—3‘methylcyclohexane. g) a cyclohexane with 2 methyl groups, both axial. cis-i-chloro-B-methylcyclohexane. h) a cyclohexane with 2 methyl groups, both equatorial. For the following pairs: a) Circle the more stable cyclohexane. b) Calculate the energy difference between the two structures, if possible. C) Indicate whether the structures are conformers (conformational isomers), constitutional isomers or stereoisomers. CH3 (b) (C) NC Et CO2H (f) CI mt—Bu f—Bu Cl Me Me 5) For every structure above, sfl the axial substituents and bfl the equatorial substituents. 6) For every structure below, draw both chair conformations. Circle the more stable conformation. Cl CH3 0 0,3. O’OH PU ,ON‘CHS CH3 ‘ - ”"0H (2/ "'F HC ‘ CN éHgCHg gr (3) (b) (C) (d) (e) (f) (9) Text Practice: 3.1-3.3, 3.5-3.7, 3.9, 3.10, 3.17-3.19, 3.25, 3.26, 3.30 ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern