New User Special Price Expires in

Let's log you in.

Sign in with Facebook


Don't have a StudySoup account? Create one here!


Create a StudySoup account

Be part of our community, it's free to join!

Sign up with Facebook


Create your account
By creating an account you agree to StudySoup's terms and conditions and privacy policy

Already have a StudySoup account? Login here

Exam 1 Study Guide Part 1

by: Udoka Oji

Exam 1 Study Guide Part 1 CHEM231

Marketplace > Brown University > Chemistry > CHEM231 > Exam 1 Study Guide Part 1
Udoka Oji
Brown U

Preview These Notes for FREE

Get a free preview of these Notes, just enter your email below.

Unlock Preview
Unlock Preview

Preview these materials now for free

Why put in your email? Get access to more of this material and other relevant free materials for your school

View Preview

About this Document

These notes cover the first part of the material for Exam 1
Organic Chemistry I
Dr. Bonnie Dixon
Study Guide
50 ?




Popular in Organic Chemistry I

Popular in Chemistry

This 9 page Study Guide was uploaded by Udoka Oji on Sunday June 5, 2016. The Study Guide belongs to CHEM231 at Brown University taught by Dr. Bonnie Dixon in Summer 2016. Since its upload, it has received 86 views. For similar materials see Organic Chemistry I in Chemistry at Brown University.

Similar to CHEM231 at Brown U

Popular in Chemistry


Reviews for Exam 1 Study Guide Part 1


Report this Material


What is Karma?


Karma is the currency of StudySoup.

You can buy or earn more Karma at anytime and redeem it for class notes, study guides, flashcards, and more!

Date Created: 06/05/16
General Chemistry Review, Structure Sunday, June 5, 2016 6:35 PM Key Ideas: • Lewis Dot Structures ○ See class notes for how to steps for drawing • Bond-line drawings provide a simplified representationfor analyzing complexorganic molecules and the reactions they undergo ○ Each apex of the bond line structure represents a carbon atom  Don't forget: the ends of the lines represent carbon atoms as well ○ Assume the octetaround carbon atoms is filled by hydrogen atoms • Resonance Useful Tips from Organic Chemistryas a Second Language: • Bond-line drawings ○ Double bonds are shown with two lines, triple bonds are show with three lines  Draw triple bonds in a straight line rather than a zig-zag, because these are typically rigid bonds  When drawing double bonds try to draw the other bonds as far away from the double bond as possible ○ When drawing zigzags it does not matter in which direction you start drawing  However,once again, try to draw the bonds as far apart as possible Screen clipping taken: 6/5/2016 6:55 PM ○ Hydrogen atomsconnected to atoms other than carbon must be drawn ○ All second-rowelements must have full octets ○ Either show all of the C's and the H's connected to them, or do not show either at all • Formal charge is a charge associated with an atom that does not exhibit the expected number of valence electrons ○ Why is it important?  Understanding structure stability  Understanding charged molecules  Understanding bonds: If carbon has a formal charge, don't assume that it has a formal charge don't assume that it has four bonds ○ Conventionis to always show formal charges and to leave out the lone pairs • Resonance is a method of drawing multiple structures for a single molecule because electrons movearound resulting in different configurations for one molecule ○ Concept: no single drawing adequately describes the nature of a the electron density spread out over the molecule out over the molecule ○ However,at the same time, you cannot simply say the molecule is flipping back and forth between different resonance structures ○ Rules  Never break a single bond  Do not exceed an octet for a second row element □ More specifically do not move electrons to atoms with sp3 hydridization □ But could have fewer ○ 3 Rules of significant resonance structures  Minimize charges  Electronegativeatoms can have positivecharges if they have an octet  Avoid drawing a resonance structure in which two carbon atoms bear opposite charges Resources • Dr. Dixon's Resonance Hand Out • Khan AcademyVideos ○ Bond-Line Structures ( chem-review/bond-line-structures/v/condensed-structures) ○ Resonance Structures ( structures/formal-charge-resonance/v/resonance-intro-jay) Acid-Base Chemistry Sunday, June 5, 2016 6:35 PM Key ideas: Acid Base Arrhenius Produce hydrogen ions Produce hydroxide ions • Bronsted - Lowry Proton Donor Proton Acceptor Lewis Electron pair acceptor Electron pair donor (Electrophile) (Nucleophile) • Amphoteric:A substance that can either serve as an acid or a base ○ Example: water • Equilibrium position is determined by stability of products vs stability of reactants Useful Tips from Organic Chemistryas a Second Language • Factors determining strength (in order of importance) ○ Electronegativityand Size  Same Row Example: Negative charge on Oxygen is morestable than a negative charge on Carbon, thus acid with Oxygen is stronger  Same Column Example: Negative charge on large Iodine is more stable than a negative charge on smaller Fluorine, thus acid with Iodine is stronger ○ Resonance  Delocalized charge is more stable than localize charge, thus acids producing resonance structures are stronger ○ Induction  Acids with electronegativeatoms on one end are stronger than acids with Carbon atoms on one end because resulting atom can more easily spread the negative charge ○ Orbitals  Negative charge on an sp hybridized Carbon is more stable than a negative charge on 3 2 an sp or sp hybridized Carbon because it is smaller and closer to nucleus, thus can more tightly hold negative charge • Predicting the Positionof Equilibrium ○ If two moleculesare competing for the proton, the direction of equilibrium will be a depicted by a larger arrow pointing in the direction of the competing moleculethat is more stable without the proton  When drawing these arrows take into consideration the fact that the top arrow represents the forward reaction and the bottom arrow represents the reverse reaction Resources • Khan AcademyVideos ○ Organic Acid-Base Chemistry ( chemistry/organic-structures/acid-base-review/v/acid-base-lewis-bronsted-lowry) • My Quizlet Flashcards ○ pKa values ( Thermodynamics; Reaction Coordinate Diagrams; Radical Reactions Thursday, June 2, 2016 8:35 PM Key Ideas: • Rate determining step has the largest ∆G (a ) (Transition state) and is the slowest step • With halogenation, Bromination is the mostsynthetically useful form of halogenation ○ Overall Exothermic ○ Largest ∆G, thus most selective • Hammond's Postulate(Reactivity - SelectivityPostulate): The slower reaction is the most selective in it's products • See class notes for how to draw Reaction Coordinate Diagrams Related Textbook Readings: • To develop an understanding of reaction mechanisms,chemists propose several sets of steps, or mechanisms,and test each proposal by carrying out experimentsthat provide experimental observationsthat will allow them to exclude mechanisms that are not consistent with facts • Reasons for doing this ○ Mechanisms provide a frameworkwithin which to organize a great deal of descriptive chemistry ○ The intellectual satisfaction derived from constructing models that accurately reflect the behavior of chemical systems ○ A mechanismis a tool to be used in the search for new informationand new understanding IR, Functional Groups, Nomenclature Sunday, June 5, 2016 6:35 PM Key Ideas: • Constitutional isomer: same formula, different backbones • Absorbance ~ % Transmittance x 100% A = ɛbc A α c ○ If the frequency of light matches the frequency of motion of the molecules,some of the light will be absorbed • In % Transmittance vs. Wavenumbergraphs, dips indicate absorption ○ Particular Functional Groups show particular characteristicsin these graphs  See class notes • Degrees of Saturation are measured with the Index of Hydrogen Deficiency(IHD) C: Carbon H: Hydrogen X: Halogen N: Nitrogen • The parent chain of a moleculehas: ○ Longest C-C ○ Chain reunited ○ End-to-end connection Prefix Infex Suffix Useful Tips from Organic Chemistryas a Second Language: • Five parts to every name: ○ Stereoismerism:indicates whether double bonds are cistrans, and indicates stereocenters (R, S), which we will cover in the chapter on configuration ○ Substituents are groups coming off the main chain ○ Parent is the main chain ○ Unsaturation identifies if there are any double or triple bonds ○ Functional group: this is the group after which the compound is named • Functional group refers to specific arrangements of atoms that have certain characteristicsfor reactivity ○ When naming compoundswith two functional groups, one will go in the suffix and the other will be a prefix in the substituent part  The listing above shows the hierarchy of how you choose as the suffix • Unsaturation (presence of double or triple bond) is indicated with an "en" for a double bond, and "yn" for a triple bond ○ For multiple double and triple bonds, use: ○ Double bonds always get listed before triple bonds • The Parent chain will be named by the number of carbons in it Screen clipping taken: 6/5/2016 11:04 PM ○ If carbon atom is a ring, we add the term cyclo  Example: ring of six carbons is called cyclohex- ○ Parent chain should be as long as possible and include the following groups (in order of importance)  Functional group (Highest ranking)  Double bond  Triple bond ○ Thus if there are no functional groups, no double bonds, and no triple bonds, then we simply choosethe longest chain possible simply choosethe longest chain possible • Everything else connected to the parent chain is called a substituent ○ Alkyl substituents follow same terminologyused for parent chains, but add "yl" to the end ○ Branched substituents have their own prefixes  Important to be familiar with tert-butyl (4 carbons) □ Three methyl groups connected to one carbon which itself is attached to the parent chain ○ Functional groups that are called substituents  OH - hydroxy  NH - amino 2  Ketone - keto  Aldehyde - aldo ○ Halogens as substituents  F - fluoro  Cl - chloro  Br - Bromo  I - iodo ○ Multiple substituents use the same prefixes used to classify the number of double and triple bonds • Stereoisomerismis the first part of every name ○ Identifies the configuration of any double bond or sterocenters ○ Two ways to arrange double bond atomsin space: cis and trans  Can only be used if we have two identical groups ○ When all four groups around double bond are different, have to use different method for naming double bonds  To be seen later in stereochemistry  Superior method • To number the parent chain properly, we begin with the same hierarchy that we used when choosing the parent in the first place: ○ If there is a functional group, number the chain so the functional group gets the lowest possible number ○ If there is no functional group, number the chain so the double bond gets the lowest possible number ○ If there is no double bond or functional group, number the chain so that the triple bond gets the lowest possible number ○ If there is no functional group, double bond, or triple bond, number so that the substituent gets the lowest possible number  If there is more than one substituent, number so the substituents get the lowest average number • Once we know the numbers we typically place them in front of each part of the moleculename to indicate which carbon each part is attached to ○ Unless the part appears on the number 1, then no need to place the number ○ For functional groups, it is ok to place the number at the beginning of the parent  2-hexanol is the same as hexan-2-ol ○ For unsaturation, use the lower number in the bond  Double bond between C2 and C3, use C2 ○ If there are multiple substituents, then every substituent must be number  Example, 2,3-dicholohexane  Example, 2,3-dicholohexane ○ If there are multiple substituents of different types, alphabetize them ○ Two numbers are always separated by commas • If a photon of light possesses exactly the amount of energy between energy levels determined by the nature of a bond, the bond can absorb the photon to promote a vibrational excitation • Bonds can stretch or bend to store vibrational energy • Different types of bonds will absorb characteristicfrequencies allowing us to determine which types of bonds are present in a compound • The frequency related unit is called the wavenumber Screen clipping taken: 6/5/2016 11:39 PM -1 -1 ○ Range from 400 cm to 4000cm ○ Higher wavenumbermeans higher energy • Signals in an IR spectrum have the following three characteristics ○ Wavenumber ○ Intensity (Strong vs. weak) ○ Shape (Broad vs. narrow) • Wavenumberis dependent on two factors ○ Bond strength: increases with bond strength ○ Atomic mass: Decreaseswith atomic mass Screen clipping taken: 6/5/2016 11:43 PM • Two regions of IR spectra ○ Diagnostic region: fewer peaks and provides the most information ○ Fingerprint region: Mostly bending vibrations, as well as stretching of single bonds. More difficult to analyze  Each compound has a unique pattern of signals in this region • Intensity of signal depends on the dipole momenton the bond ○ Larger dipole momentshave larger signals • Carbonyl groups often produce the strongest signals, while C=C often produce fairly weak signals • Intensity of signal derives from number of bonds contributing to the signal as well • Shape of signal depends on the uniformity in strength of bonds contributing to the signal ○ Characteristic bonds with a large distribution of bond strength will have a broad signal • Symmetricstretching and asymmetricstretching also contribute signal shape Resources: • Dr. Dixon's NomenclatureBasics Handout • Dr. Dixon's Functional Groups Handout • Khan AcademyVideos: ○ Naming Alkanes ( structures-alkanes-cycloalkanes/naming-alkanes/v/representing-structures-of-organic- molecules) ○ Naming Alkanes, Cycloalkanes,and bicyclic compounds ( cycloalkanes/naming-alkanes-cycloalkanes-bicyclic/v/alkane-and-cycloalkane-nomenclature- i) • My Quizlet Cards ○ Carbon Parent Chain Names


Buy Material

Are you sure you want to buy this material for

50 Karma

Buy Material

BOOM! Enjoy Your Free Notes!

We've added these Notes to your profile, click here to view them now.


You're already Subscribed!

Looks like you've already subscribed to StudySoup, you won't need to purchase another subscription to get this material. To access this material simply click 'View Full Document'

Why people love StudySoup

Steve Martinelli UC Los Angeles

"There's no way I would have passed my Organic Chemistry class this semester without the notes and study guides I got from StudySoup."

Allison Fischer University of Alabama

"I signed up to be an Elite Notetaker with 2 of my sorority sisters this semester. We just posted our notes weekly and were each making over $600 per month. I LOVE StudySoup!"

Bentley McCaw University of Florida

"I was shooting for a perfect 4.0 GPA this semester. Having StudySoup as a study aid was critical to helping me achieve my goal...and I nailed it!"

Parker Thompson 500 Startups

"It's a great way for students to improve their educational experience and it seemed like a product that everybody wants, so all the people participating are winning."

Become an Elite Notetaker and start selling your notes online!

Refund Policy


All subscriptions to StudySoup are paid in full at the time of subscribing. To change your credit card information or to cancel your subscription, go to "Edit Settings". All credit card information will be available there. If you should decide to cancel your subscription, it will continue to be valid until the next payment period, as all payments for the current period were made in advance. For special circumstances, please email


StudySoup has more than 1 million course-specific study resources to help students study smarter. If you’re having trouble finding what you’re looking for, our customer support team can help you find what you need! Feel free to contact them here:

Recurring Subscriptions: If you have canceled your recurring subscription on the day of renewal and have not downloaded any documents, you may request a refund by submitting an email to

Satisfaction Guarantee: If you’re not satisfied with your subscription, you can contact us for further help. Contact must be made within 3 business days of your subscription purchase and your refund request will be subject for review.

Please Note: Refunds can never be provided more than 30 days after the initial purchase date regardless of your activity on the site.