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Orgo I Exam 1 Review

by: Heli Patel

Orgo I Exam 1 Review 3331

Heli Patel

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Exam 1 notes + reviews from practice test
Organic Chemistry 1
Mary Bean
Study Guide
orgo, Organic Chemistry, exam1
50 ?




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This 12 page Study Guide was uploaded by Heli Patel on Thursday September 22, 2016. The Study Guide belongs to 3331 at University of Houston taught by Mary Bean in Fall 2016. Since its upload, it has received 67 views. For similar materials see Organic Chemistry 1 in Organic Chemistry at University of Houston.


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Date Created: 09/22/16
Organic I Chemistry  Exam 1 Review   Review Concepts that are on the Bean’s exams with practice test examples !!! Acids and Bases : Curved Arrow Formalism : The Mechanism  1. Curved Arrow are used to indicate bonds breaking and forming in a reaction or  electron “flow”. 2. Direction of electron “flow” is always from the electron rick to the electron poor  or from nucleophile to electrophile, never the reverse.  3. Arrow begins with a covalent bond or a lone pair of electron or a lone electron. 4. Arrow show where the electron flow not where the atoms go. 5. Base are the one with most of the time the negative charge and with the spectator ion. Spectator ion as the reaction proceeds ends up with the conj base Isomers  Question : monochlorination  of compound  Find all the diff environment  5 diff environment  (a,b,c,d,e) Add the Cl to each different  environment  For this question 4th and the 5th environment there  2 geometric isomers each ­ Wedge­dash diagrams. Usually drawn with two bonds in the plane of the page, 1  in front, and one behind to give the molecule perspective ­ 1 dash and 1 wedges are considered two different geometric isomers  Newman Projections Eclipsed ­ least stable because the H are all in the same area  Staggered ­ most stable because the H are divided to be far away from each other Ranking Boiling point : Rules  1. Bond strength ­ stronger the strength higher the BP (IMF) a. H­bonding > Dipole­dipole(Polar) > LD (non­polar) 2. Size ­ bigger the size the larger the BP 3. Branching ­ Larger the surface area hence the higher the BP. 4. More the H­bonding and higher the BP. Ranking Acidity: Rules  1.  ­ gives off H+ 2. More stable conj base  3. Stronger the acid  4. How to determine the conj base strength  a. Resonance ­ delocalize the charge  b. Size­ polarizability  c. EN ­ holds regulating charge or electron better  Nomenclature (IUPAC) 1. Find the longest parent chain with the highest priority functional group  2. Parent hain needs to include as many substituents  as possible  3. Substituent should have the lowest possible numbering  4. Put together the substituents in alphabetical order  5. Functional group : Alcohol, Alkene, Alkene  1. Need to Know how to place them and read them on the line angle diagram  Resonance Structure  1. Resonance structure differ only in the placement of electrons not atoms. Only the  pi bonds and the lone pair “move”. 2. If overall charge of compound is + only 1 arrow is used  3. If overall charge of compound is ­ then 2 arrow are used. 4. Do not repeat structures  Rule to determine major contributors  1. all octet rule  2. EN :  least EN atom holds + more stable, most EN atom holds ­ more stable 3. Less  charge  separation  Hybrid     Line Angle  ­ Condensed chemical formulas show the hydrogen atoms (or other atoms or  groups) right next to the carbon atoms to which they are attached. ­ Line­angle formulas imply a carbon atom at the corners and ends of lines. Each  carbon atom is understood to be attached to enough hydrogen atoms to give each carbon  atom four bonds. ­ Formal Charge  =[# of valence electrons] – [electrons in lone pairs + 1/2 the # of bonding electrons] Or  = [# of valence electrons on atom] – [non­bonded electrons + number of bonds]. Orbitals  ● An orbital is a wave function for an electron defined by the three quantum  numbers, n, ℓ and l. Orbitals define regions in space where you are likely to find  electrons. ● s orbitals (ℓ = 0) are spherical shaped. ● p orbitals (ℓ = 1) are dumb­bell shaped. ● The three possible p orbitals are always perpendicular to each other Electron Configuration  ­ Aufbau principle, the electrons of an atom occupy quantum  levels or orbitals starting from the lowest energy level, and proceeding to the  highest, with each orbital holding a maximum of two paired electrons  ­ Pauli exclusion principle is the quantum mechanical principle  that states that two identical (particles with half­integer spin) cannot occupy  the same quantum state simultaneously ­ Hund's rule states that: 1. Every orbital in a sublevel is singly occupied before any orbital is doubly occupied. 2. All of the electrons in singly occupied orbitals have the same spin (to maximize total spin). 17. Hybridization  ● atomic orbitals fuse to form newly hybridized orbitals, which in turn, influences molecular geometry and bonding  properties ● tch? v=YcSPPKESpwc Lewis Diagram  1.  Determine the total number of valence electrons in a molecule 2. Draw a skeleton  3. Consider the remaining electrons and place them so as to fill the octets of as  many atoms as possible (start with the most electronegative atoms first. 4. If the octet rule is not yet satisfied for the central atom, draw the double or  triple bonds between it and the surrounding atoms using lone pairs.  5. Check that you have the lowest formal charge possible for all the atoms,  without violating the octet rule;   Bonding ­ Hydrogen bonds only form between hydrogen and oxygen (O), nitrogen (N)  or fluorine (F). ­ An ionic bond is formed when one atom accepts or donates one or more of its valence electrons to another atom. ­  A covalent bond is formed when atoms share valence electrons. Practice TEST examples  Conformation examples­chemistry/bond­line­structures­alkanes­ cycloalkanes/conformations/v/drawing­chair­conformations 


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