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Exam I Study Guide: Organic Chemistry

by: Audrey Hernandez

Exam I Study Guide: Organic Chemistry CHEM 2410

Marketplace > University of Toledo > Organic Chemistry > CHEM 2410 > Exam I Study Guide Organic Chemistry
Audrey Hernandez
GPA 3.6

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About this Document

This study guide asks the student questions while providing some insight to answers to prepare for exam I of organic chemistry.
Organic Chemistry 1
Joseph Schmidt
Study Guide
Science, Chemistry, organic, Organic Chemistry
50 ?




Popular in Organic Chemistry 1

Popular in Organic Chemistry

This 6 page Study Guide was uploaded by Audrey Hernandez on Saturday September 17, 2016. The Study Guide belongs to CHEM 2410 at University of Toledo taught by Joseph Schmidt in Fall 2016. Since its upload, it has received 47 views. For similar materials see Organic Chemistry 1 in Organic Chemistry at University of Toledo.


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Date Created: 09/17/16
Organic Chemistry I Exam I Study Guide  Dr. Joseph Schmidt   Chapter 1    ❖ Structure and bonding  ➢ What are the types of bonding?  ■ Ionic  ■ Covalent  ● Nonpolar  ● Polar  ➢ Which is the stronger bond?  ■ Covalent, and bond strength increases as the bond length decreases  ● Single bonds are longest and weakest  ● Triple bonds are shortest and strongest  ❖ Electronegativity   ➢ How does this relate to electron affinity?  ■ The stronger the electronegativity the stronger the electron affinity  ➢ How does this relate to ionization energy?  ■ The stronger the electronegativity the more ionization energy is required  to take away its electrons  ❖ Resonance structures  ➢ Easiest way to make these is to count the number of electrons   ■ Electron # has to be the same throughout the structures  ➢ Octet Rule  ■ Atoms will want to have full outer valence electron shells  ➢ Formal Charge  ■ Formal charge = # of valence electrons of the atom ­ (½)(# of bonded  electrons) ­ # of nonbonding electrons  ❖ Shape and functionality  ➢ What does VSEPR stand for?  ■ Valence­Shell Electron Pair Repulsion   ■ It states that electrons will spread out as far as they can from each other to  minimize the repulsions felt  ➢ What kinds of geometrical shapes can form?  ■ Linear  ● Has 2 electron dense regions  ● Bond angle usually about 180 degrees  ■ Bent  ● Has four electron dense regions, two of them being electron lone  pairs  ● Bond angle usually a little less than 109.5 degrees  Organic Chemistry I Exam I Study Guide  Dr. Joseph Schmidt   ■ Trigonal planar  ● Has three electron dense regions  ■ Trigonal pyramidal   ● Has four electron dense regions, one of them being an electron  lone pair  ● Bond angle usually a bit less than 109.5 degrees  ■ Tetrahedral   ● Has four electron dense regions  ● Bond angle usually about 109.5 degrees  ➢ How can a molecule be nonpolar but have polar bonds?  ■ That answer likes in the structure and shape of the molecule  ● If we have CCl​  then we know that the Cl will be more negative  4​ and the C more positive, resulting in polar bonds.  However, it is a tetrahedral shape which makes the polar bonds  cancel out so the overall molecule itself is nonpolar.  ➢ Match the principle names with their concepts    A. States that no more than two   oppositely spinning electrons  can occupy each atomic orbital 1. Aufbau Principle     B. States that an electron will go  into the lowest energy atomic 2. Hund’s Rule  orbital available    C. States that when there a multiple 3. Pauli Exclusion Principle  atomic orbitals of the same energy  level, an electron will occupy an  empty orbital before coupling  with another electron    ❖ Hybridization  ➢ What is the difference between Valence Bond Theory and Molecular Orbital  Theory?  ■ Valence Bond Theory is a model for bonding by showing the overlapping  orbitals of close contact atoms  ■ Molecular Orbital Theory mathematically create combinations of atomic  orbitals    Organic Chemistry I Exam I Study Guide  Dr. Joseph Schmidt   ➢ How do you calculate the bond order?    ➢ Why do some atoms hybridize their atomic orbitals?  ■ To obtain their desired number of valence electrons  ● An example would be carbon hybridizing its orbitals  ■ To make lone pairs the same level of energy   ● An easy example would be oxygen hybridizing its orbitals so its  two electron lone pairs are on the same level of energy  ➢ What are the reactive carbon atom species? How are their atomic orbitals  hybridized?   ■ Carbocations  2 ● Have three regions of electron density → sp​    ● Has an empty p orbital  ■ Carbanions  ● Has four regions of electron density with one of them being a lone  pair → sp​   ■ Radicals  ● Is an exception to the VSEPR rules  ● Has one unpaired electron that resides in the p orbital of a sp​  hybrid    Chapter 2    ❖ Acid and Bases  ➢ What is the difference between a Bronsted­Lowry and a Lewis acid/base?  ■ Think, which one deals with protonation and hydrogen atoms and which  deals with exclusively electron pairs?  +​ ● Bronsted­Lowry deals with protonation and hydrogen ions (H​ )  ● Lewis deals with transference of electron pairs from bases to acids  Organic Chemistry I Exam I Study Guide  Dr. Joseph Schmidt   ➢ What does it mean to be a nucleophile or an electrophile?  ■ These apply to the Lewis acids/bases  ■ A nucleophile is a Lewis base  ● It is electron rich and wants to find a nucleus to donate its electrons  to  ■ An electrophile is a Lewis acid  ● It is electron deficient and wants to accept or take in electrons  ➢ What helps stabilize the conjugate base of an acid?  ■ Electronegativity  ■ Inductive effects  ■ Size of negatively charged atom  ■ % of s orbital in a hybrid orbital  ➢ What is the Henderson­Hasselbach equation?  ■ pK​  = pH + log([HA]/[A​])  ­​ a​   Chapter 3    ❖ Organic Compounds  ➢ What are the different subclasses of hydrocarbons and what are the difference  between them?  ■ Alkanes  ■ Alkenes  ■ Alkynes  ■ Saturated  ■ Unsaturated  ➢ What is the basic formula for an alkane?  ■ C​ H​ n​ 2n+2  ➢ Name the following chemical compounds  ■ CH​ 4  ■ C​ H2​ 6  ■ C​ H3​ 8  ■ C​ H4​ 10  ■ C​ H5​ 12 ➢ What does the suffix “­yl” indicate?  ■ That one of the terminal hydrogens has been removed to connect the  molecule to something else  ❖ Functional groups  ➢ List basic formulas for the following, using R as a placeholder for unimportant  parts of the molecule  Organic Chemistry I Exam I Study Guide  Dr. Joseph Schmidt   ■ Alcohol  ● OH attached to a carbon  ■ Ethers  ● Has an oxygen attached to two carbon atoms  ■ Amines  ● Nitrogen that is attached to only carbon and hydrogen atoms  ➢ Take the following molecule and label the primary, secondary, tertiary, and  quaternary carbons.      ➢ What the difference in how alcohols and amines are labeled in degree?  ■ Alcohols carry label of carbon they are bonded to  ■ Amine’s label depends on the number of carbons bonded to the nitrogen  ➢ What’s the positioning difference of the C=O bond in a aldehyde and a ketone?  ■ C=O in an aldehyde is in between a carbon and hydrogen atom  ■ C=O in a ketone is in between two carbon atoms  ■ Carboxylic acids have their C=O between a carbon atom and an OH group  ■ Esters C=O group is between a carbon and O­R group  ● Remember that “R” is just a placeholder for the rest of a molecule  ■ Amide will have the C=O between a carbon atom and a NR​  group  2​                 Organic Chemistry I Exam I Study Guide  Dr. Joseph Schmidt   ➢ Name the following compound     ➢ Draw the above compounds different resonance structures and name each one 


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