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

CHEM 220: Organic Chemistry Notes Chapters 2-4

by: Cal Somers

CHEM 220: Organic Chemistry Notes Chapters 2-4 CHEM 220

Marketplace > Kalamazoo Valley Community College > Chemistry > CHEM 220 > CHEM 220 Organic Chemistry Notes Chapters 2 4
Cal Somers
Kalamazoo Valley Community College

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 introduction to functional groups, acid/base chemistry, nomenclature of molecules, Newman Projections, Cyclic alkanes, and Hydrogenation
Organic Chemistry
Mark Lovdhal
Organic Chemistry
75 ?




Popular in Organic Chemistry

Popular in Chemistry

This 10 page Bundle was uploaded by Cal Somers on Monday February 8, 2016. The Bundle belongs to CHEM 220 at Kalamazoo Valley Community College taught by Mark Lovdhal in Winter 2016. Since its upload, it has received 21 views. For similar materials see Organic Chemistry in Chemistry at Kalamazoo Valley Community College.

Similar to CHEM 220 at Kalamazoo Valley Community College


Reviews for CHEM 220: Organic Chemistry Notes Chapters 2-4


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: 02/08/16
CHEM 220: Organic Chemistry  Functional Groups o Familiar structures of atoms that make up more complex molecules o Structures vary from simple hydrocarbon chains to combinations of carbon, oxygen, nitrogen all having a different effect in reactions o Reactions of these complex molecules can be mapped out with reaction schemes o Groups are:  Alkanes: Single bonded chains of hydrocarbons  Alkenes: Hydrocarbons with a double bond  Alkynes: Hydrocarbons with a triple bond  Cyclic Structures: Ring shaped hydrocarbons  Alcohols: Oxygen and hydrogen attached to an alkane  Halogen: Halide group attached to carbon  Ethers: Oxygen two alkanes on either side  Amines: Nitrogen connected to alkane chains  Aldehydes: Oxygen double bonded to the end of a carbon chain  Ketones: Oxygen double bonded with carbon  Carboxylic Acid: Oxygen double bonded to an alkane that’s connected to an alcohol group  Identifying Primary, Secondary, Tertiary (1 , 2 , 3 )o o Each one identified by how many atoms are attached to a substance o Each one follows certain reaction rules o Primary (1 ): One other carbon attached o Secondary (2 ): Two carbon attachments o Tertiary (3 ): Three carbon attachments  Degrees of Unsaturation o Most alkanes follow the general formula C H 2n 2n+2 o Degrees of unsaturation is the of two hydrogen atoms with a ring or π bond o If no hydrogen atoms are missing the molecule is saturated o Alkanes missing hydrogen atoms are unsaturated o The maximum amount of hydrogen atoms follows the general formula o DU helps identify structural features of a molecule o Formula: ( ′ ) ( ′) [ ???????????????????????????? ???????????????????? ???????? ???? ???? − ???????????????????????? ???????????????????????? ???????? ???? ???? ] 2 ½(2C+2+N-H-X) # of rings=1+(# of carbons)-1/2(# of hydrogens)-(# of pi bonds)  Infrared Spectrometry o IR spec is a way to determine what functional groups are in a molecule o Bonds between molecules vibrate at different resonant frequencies in conjunction with frequency of light o Functional groups are identified by different peaks in different regions of graph -1 o Fingerprint region: 400-1400 cm (Used as additional help to diagnostic region)  Identifies most single bonds (C-C, C-N, C-O) o Diagnostic Region: 1400-4000 cm (Main region for identifying functional groups) -1 o Alkanes appear slightly before 3000 cm  C-C double bonds appear around 3200  C-C triple bonds appear at 3300 o Peaks around 3200-3600 cm are alcohol groups  Deep, wide peaks indicate hydrogen bonding (carboxylic acids/alcohol groups)  Thin peaks indicate little to no hydrogen bonding like in ketones or aldehydes o Amines appear at 1000-2000 and 3350-3500 cm 1+  Medium depth, pointy peaks with either one or two larger peaks  One large peak indicates primary amine, two indicates secondary amines o Aldehydes 2750-2850  Shallower, sharp peaks that continue from alkane peaks  Distinct peak around 1750 indicating C-O double bond o Ketones/C-O Double bonds 1650-1800  No peaks near alkane peaks  Super sharp deep peak near 1700-1750 o Benzenes  Lots of double bond/alkane peaks  Medium sized peaks around 1450-1600 o NOTE: Molecules with heavy electron density shifts values down slightly  Bronstead-Lowry Acids and Bases o Involves only the transfer of hydrogen ions (H+)  Bases are proton (H+) acceptors  Acids donate these proton to the bases o Conjugates of each form because of the transfer of protons  Conjugate acids are bases that have accepted protons  Conjugate bases are acids that have given up their proton, usually having a negative charge in the products  So conjugates are just flip-flopped products of the reactants o NOTE: Strong acids form weak conjugate bases and strong bases form weak conjugate acids o Any extra atoms or molecules that do not participate in the reaction are called spectator ions  Lewis Acids/Bases o Involves the transfer of electrons rather than just protons  Acids accept electrons  Bases donate electrons (usually to pick up an atom from the acid) o So, Bronstead acids and bases are also Lewis acids and bases but Lewis acids and bases aren’t always Bronstead acids and bases. o Nucleophiles are usually Lewis bases  Electron rich atoms ready to donate electrons o Electrophiles are usually Lewis acids  Electron poor atoms needing a nucleophile  pKa vs. Acid Strength o Ka and pKa are both measures of the strength of acid strength derived from the point of equilibrium equation  Equilibrium equation is concentration of products over reactants, usually having water as one of the reactants  Since most acid/base reactions are diluted water can act as a constant in the equilibrium equation and be taken out leaving us with the formula for Ka o Ka values can be really large (larger Ka means a stronger acid) so a logarithmic scale is used  The negative log of the Ka value gives something called a pKa value  pKa can usually be used to find the overall pH of a solution o Smaller pKa values means stronger acids  Predicting acid strength o There are 4 important considerations to predicting general acid strength  Electronegativity-An atoms affinity (necessity) to carry electrons very close to its nucleus. Electronegativity increases going right and upwards across the periodic table. Acidity increases the same way. Fluorine is the most electronegative atom; noble gasses are not included because they already have a full octet.  Inductive effects-Distance between atoms in a molecule. Induction is a physics concept where electricity is transferred to materials a certain distance away. More electronegative atoms have greater inductive effect. The number of inductive atoms and the closer an inductive atom is to the acidic side of a molecule the more effect it will have, increasing the pKa value.  Resonance-A molecules ability to move electrons about its structure. The more resonance a molecule has the more stable it is and the less acidic it will be.  Hybridization-Shape of atomic orbitals. Less stable and less clustered molecules will be more acidic. This means molecules with smaller/less substituents an more single bonds will be more acidic. The more s-character a molecule has, the more acidic it will be  Solvent effects o Acids are not as efficient in a dry environment as they are in a solution because there is not an efficient way to transfer acidic molecules to bases o For the most part, acid/base reactions are diluted to create a protective coating around the acid allowing easier interactions of the charged molecules. This is called solvation o Since water is polar it can sometimes have an effect on the overall reaction  Using a non-aqueous solvent (molecule with little chance of donating or accepting electrons) will limit the effect on a molecule o A solvent with no acidic protons or something that will not transfer electrons and will dissolve the starting material should be used  IUPAC Nomenclature o General rules: 1. Identify the longest chain of carbons with the most substituents attached 2. Number the longest chain so that the substituents have the lowest numbers possible 3. Identify and name the substituents 4. Arrange the substituents alphabetically  Make sure to place location number in front of substituents  Use di, tri, tetra, etc. to indicate multiples of the same substituent o NOTE: Functional group substituents have naming priority; the main effect of this is the change in the ending/beginning of the name. I’ll put “has naming priority over…” so you know to use the proper ending/beginning.  So, carboxylic acids would take priority over naming of alcohols, you would use –oic acid ending and have the alcohol as a hydroxy branch rather than naming it after the alcohol. o Naming Branches  Common names for short alkane branches (methyl, ethyl, propyl, etc.)  Tert-butyl is a methyl group with three methyl attachments (looks like a peace sign)  Iso-propyl is a methyl group with two methyl substituents (looks like a line connected to two fingers)  Sec-butyl is like a butyl group attached to a methyl (almost like an uneven iso-propyl group)  Neo pentyl is an ethyl group with three methyl attachments at the end (looks like a stick snowman arm with an elbow) o Alkenes/Alkynes  Select the parent chain with the double bond (for alkenes) or triple bond (for alkynes) having the lowest number.  The rest of the alkene follows General IUPAC rules  When arranging the name, alkenes drop the –e ending and add –ene  Similarly, alkynes drop the –e and add –yne  Ex.) PropanePropene (alkene) Propyne (alkyne)  Lowest in naming priority next to alkanes o Cyclics  Follows General IUPAC naming rules adding cyclo- to the beginning  If one of the attachments to the ring is longer than the ring chain then the ring is an attachment.  If this happens, the ring is named like an alkane branch with cyclo- in front of it  Does not participate in naming priority, if theres a ring, your going to have cyclo- somewhere in the name o Halides  Select the longest chain with the lowest number branches including the halide  Halides follow general IUPAC rules, being named as branches, and having the lowest numbers, not a part of the structure  Name is added with an –o ending (Bromo, Chloro, Iodo, etc.)  Ex.) 2-Bromo-3-methylbutane  No naming priority since their named as branches o Alcohols  Select the longest chain with alcohol attached, giving the lowest possible numbers  Number in front of name, drop the –e and add –ol  Ex) Propane Propanol  Naming priorities over alkenes/alkynes  Keep the –e or –y from the name but add –ol  2-propene2-propenol with an alcohol  When in a molecule with aldehydes, ketones, or carboxylic acids, name as a hydroxy branch. o Amines  Find the longest chain including the amine with the lowest numbered substituents including the substituents  Drop the –e ending and add –amine to it.  Naming can be combined with lower priority groups  Its possible to have something like propanolamine, just make sure to be careful  For higher priority groups (aldehydes, ketones, carboxylic acids) name as an amino- branch  If there are alkane branches connected to the nitrogen group, the location is noted by an N- followed by the branch name o Aldehydes/Ketones  Numbering of the longest chain for aldehydes always starts at the C=O bond  Add –al to the ending  Numbering for ketones is the lowest numbers possible  Add –none to the ending  Follows other general IUPAC rules  Naming priority over everything except carboxylic acids o Carboxylic Acids  Named from the longest chain starting at the C=O bond  Drop the ending, add –oic acid if it’s the whole carboxylic acid  If carboxylic acid is in the ion form (missing the H from hydroxyl group, creating a negative charge on the oxygen) its ending is –oate  Ethane/Butane Conformations o Single bonds allow for rotation of a molecule o Rotation is called dihedral angle, each rotational is around 60 o  This rotation gives a molecule different energy levels depending on the repulsion between electron clouds of individual atoms (torsional strain)  i.e. you can’t put two of the same ends of a magnet together o Lowest energy formation is when atoms are the farthest possible distance apart o Using something called Newman Projections, we can look down the bonds in between carbon atoms and visualize the rotation and see if there are atom interactions o For ethane, CH —C3 , th3re are only two different possibilities for energy levels  Staggered-all atoms attached to the carbon bonds are the farthest possible distance from each other having the lowest energy level  Basically a circle divided into six pieces but with three lines in front of the circle and three lines behind the circle  Eclipsed-atoms from staggered position are rotated to the right 60 (easier to keep the 3 in back in the same spot and only rotate the ones in the front placing the lines next to the ones in back)  This is the highest possible energy formation o Butane has a cycle of rotations, so rotating to the right, when the two methyl groups at either end are closest they can be (fully eclipsed) they are at the highest energy and further rotation is just a mirrored form of the beginning rotations until you get back to the same place. Each following descriptions for butane newman projections are o rotating right 60  Anti- staggered form where the two methyl groups are at opposite ends, farthest they can be away from each other. This is where to start (one methyl at the top, one at the bottom) o  First eclipse- front three are rotated 60 to the right, placing the methyl from the top next to the Hydrogen to the immediate right. This has a higher energy than the staggered forms but lowest eclipsed energy o  Gauche-Staggered form rotated another 60 to the right. Now the two methyl groups are almost next to each other, but not eclipsed. Highest energy of all staggered forms of butane  Fully Eclipsed- Eclipsed form where two methyl groups are directly overlapping each other. Highest energy and least stable formation  If you keep rotating 60 to the right each time, you will go through the same types of formation with the same energy, except the methyl group in the front will be on the left side of the molecule. o The energy diagram for these looks like 3 connected waves, the eclipsed forms, highest in energy, are at the top, with fully eclipsed being the middle wave and all staggered forms are at the bottom, in between the wave peaks  Cyclic Alkanes o The normal bond angle for any sp carbon is 109.5 , this comes from VSPER theory where each sp atom has a tetrahedral geometry and atoms want to be as far as possible from other atoms o When cyclic structures form, this forces the atoms to have smaller bond angles and strain is put on each bond, called ring strain o The less atoms that make up a ring, the smaller the bond angles, and the more stain there is  Cyclopropane (triangle shape) has bond angles around 60 and o a ton of ring strain  Cyclobutane (square) has 88 bond angles, less strain than cyclopropane  Cyclopentane (pentagon shape) has about 108 bond angles and has very little strain on it  Cyclohexane (Hexagon shape) bond angles are really close to o 109.5 that it experiences only a small amount of ring strain o So, overall the size of the ring greatly effects the strain on the bonds between molecules. Cyclohexane has the least amount of ring strain since the bond angles are so close to what they naturally are, 109.5 o  Cyclohexane conformations o Cyclohexane is the most natural ring formation because the bond angles are close to 109.5 o Although rings look flat on paper, to achieve the least amount of torsional strain they take on 3-D arrangements  Cyclohexane actually looks like a crown in 3-D o Like other molecules, cyclohexane can take on many different conformations. Two formations are the most important  Chair Formation  Boat Formation o Chair form (preferred formation) looks like a tri-fold chair you see at beaches  In this form there is the least amount of torsional strain on each atom, and if you draw a Newman projection, you can see that each atom in the molecule is in a staggered formation o Boat formation looks like a boat, where each end of cyclohexane points upwards  A lot of torsional strain on each bond comes from each atom being in an eclipsed formation looking at the Newman projection o Atoms that do not contribute to the overall shape of cyclohexane (attached to the outside of the ring) can have two positions on the ring  Axial position-Points either up or down from the ring  If you draw 2-D cyclohexane on paper (hexagon) the axial positions would be perpendicular to the plane of the paper, either pointing upwards towards the viewer or downwards through the paper  Equatorial position-Points away from the ring  On the same plane as the paper from the example above o Cis/Trans Isomerism can exist on cyclohexane, and there are different clues for each substituent position on the ring. The easiest way to view these is build a molecular model with cyclohexane, attach substituents in the positions posted below, and flatten the ring out.  If the substituents are on the same side of the ring, they are cis. If there’s one on each side of the ring, they are trans.  1,2 position substituents  If both are axial or equatorialtrans  If one axial and one equatorialcis  1,3 position substituents  If both are axial or equatorialcis  If one is axial and one equatorialtrans  1,4 position substituents  Both are axial or equatorialtrans  One axial, one equatorialcis  Hydrogenation o First and easiest reaction in your chemistry tool kit o Reaction eliminates all double or triple bonds in a molecule and reduces them to single bonds o “Ingredients” needed for reaction: These are the things you would write on the reaction arrow pointing from reactants to products  Metal catalyst: Paladium (Pd), Nickel (Ni), or Platinum (Pt)  Source of Hydrogen (H )2  Non-aqueous solvent: Ethanol (EtOH) Ethyl acetate (EtAc) or similar substances o Using Platinum in this reaction can also reduce ketones and aldehydes to alcohols along with the double or triple bond.  To avoid this, only use Paladium or Nickel with an alkene that also has a ketone or aldehyde


Buy Material

Are you sure you want to buy this material for

75 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

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!"

Kyle Maynard Purdue

"When you're taking detailed notes and trying to help everyone else out in the class, it really helps you learn and understand the I made $280 on my first study guide!"

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."


"Their 'Elite Notetakers' are making over $1,200/month in sales by creating high quality content that helps their classmates in a time of need."

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.