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CHEM:341 Organic Chemistry I Week 4 Notes

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CHEM:341 Organic Chemistry I Week 4 Notes CHEM341

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These are the notes for week 4 of Organic Chemistry I. Note that we didn't have class Monday due to the exam Tuesday so there is less material.
Organic Chemistry
Anna Elizabeth Allen
Class Notes
Organic Chemistry
25 ?




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This 4 page Class Notes was uploaded by Raffasarru on Friday September 16, 2016. The Class Notes belongs to CHEM341 at Colorado State University taught by Anna Elizabeth Allen in Fall 2016. Since its upload, it has received 5 views.


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Date Created: 09/16/16
CHEM:341 Organic Chemistry I Week 4  3D Representation of Molecules o Since most molecules are not flat, need ways of representing their three- dimensional space using:   Wedge and Dash   Dash: behind, Wedge: in front, lines: in plane  Sawhorse   Newman Projection   Big circle represents back carbon since it can’t be seen  45° rotation between each one o How to draw a Newman Projection  1) identify three groups on front carbon (front determined by arrow or numbers)  2) identify three groups on back carbon  3) put them together 1  Wedges should end up beside each other, dashes beside each other, in plane opposite each other  Conformation of Alkanes o Definition: Conformations are different arrangements of atoms that are interconverted by a rotation around single bond o Conformers: same molecules in different positions that often have different energies which are related by bond rotation o Butane (these aren’t the only conformations):  o Torsional Strain: an increase in energy caused by eclipsing interactions  Caused by rotation between carbons  Staggered spreads out positive charge of substituents while eclipsed brings them together, which causes torsional strain  Lowest energy to highest energy: ???? < ???? < ???? < ????  Anti-conformation: methyl groups opposite each other, lowest energy  Gauche interaction: when two groups (not two hydrogen) are 60° apart  Generally, staggered is low energy; eclipsed is high energy o Butane angle v. energy graph 2  o Ethane angle v. energy graph  o Summary of Alkane Conformational Energies:  1) Eclipsed conformations are higher in energy than staggered of same molecule  2) Highest energy conformation comes from largest two groups eclipsing  3) Lowest energy conformation comes from largest groups being anti- staggered (opposite each other)  In open chain (non-cyclic) molecules, conformations are usually averaging rapidly at room temperature, molecules assume conformations proportional to energy  More stable means more abundant Chapter 3: Alkenes and Alkynes  Alkenes are hydrocarbon molecules that contain a ???? − ???? double bond (???? = ????) o Hybridization of a carbon in a double bond is ???????? 3 o The double bond consists of one sigma bond (???? − ????????????????) and one pi bond (???? − ????????????????) o The ???????? orbitals are used to make strong ???? − ????????????????????, ???? orbital is used to make a ???? − ????????????????  Bonding and Molecular Orbitals in Alkenes o Reactivity of ???? and ???? bonds: ???? − ???????????????????? are generally more stable and harder to break than ???? − ???????????????????? o However, breaking both bonds is harder than breaking just a sigma bond, don’t get confused  Consequence of ???? − ???????????????? o While most alkanes can rotate around their ???? − ????????????????????, alkenes cannot rotate around ???? = ???? bonds o Pi bond is result of side-on overlap of ????-orbitals, rotation will break the overlap because perpendicular interactions cancel out o Lack of rotation leads to opportunity for isomers  Trans: opposite side  Cis: same side  E (entgegen) (opposite) is Trans in a Newman Projection  Z (Zusammen) (together) is Cis in a Newman Projection   Alkynes: Bonding and Hybridization o Alkynes are hydrocarbon molecules that contain a ???? − ???? triple bond o The triple bond results from overlap of ???? orbitals above and below the original bond o ???????? orbitals are used for strong sigma bonds, ???? orbitals are used for pi bonds o A triple bond consists of 1 ???? − bond and 2 ???? − bonds 4


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