Organic Chemistry Study Guide Test 1
Organic Chemistry Study Guide Test 1 CH 186 - 01
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This 8 page Study Guide was uploaded by Jessica Niswonger on Friday January 8, 2016. The Study Guide belongs to CH 186 - 01 at Southeast Missouri State University taught by Philip W Crawford (P) in Fall 2015. Since its upload, it has received 108 views. For similar materials see Found of Inorganic Chemistry in Chemistry at Southeast Missouri State University.
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Date Created: 01/08/16
- How are lewis structures used in organic chemistry?To represent covalent bonding - What is ionic bonding? Electrostatic interaction between ions - When representing ionic bonding how do you draw the atoms? With no lines between them. - What is the formal charge? Valence electron contribution from an atom in a molecule - What is the formula for fc? Valence e – ½(bonding e) – any lone e - Do you count double and triple bonds in bonding e? yes - What do you do to make a charge stand out circle it - What are the steps in writing lewis structures? o 1 add up all valence e for all atoms. 2 draw skeletal structure. 3 draw single bonds between atoms and subtract e used from. 4 fill ocets. - How can formal charges be used when drawing lewis structures? o To determine whether the octet should be filled with a lone pair or an extra bond. - Can you break the octet rule when making resonance structures? o Only for carbon - What two types of electrons can move in resonance structures? o Lone pair e and e in double and triple bonds - What kind of bond can you not break when creating resonance? o Sigma bonds - How do you determine if you have enough steps before moving on to the resonance structure? o If the overall charge has remained the same as the initial form - What is defined as a major resonance contributor? o The structure with the lowest energy, least extra fc’s on atom. - What is vespr used for? o How shapes of molecules affect reactivity, to determine geometry around the atom. - What is the definition for electron geometry o General category - What is the definition of molecular geometry? o A specific shape - What is the electron geometry for 2 groups around the central atom o Linear - What is the electron geometry for 3 groups around the central atom o Trigonal planar - What is the electron geometry for 4 groups around the central atom? o Tetrahedral - What is the molecular shape, angle, hybrid. for 2 bonds and 0 lone pairs? o Linear, 180, sp - What is the molecular shape, angle, hybrid. For 3 bonds and 0 lone pairs? o Trigonal planar, 120, sp2 - What is the molecular shape, angle, hybrid. For 2 bonds and 1 lone pair? o Bent less than 120, sp2 - What is the molecular shape, angle, hybrid for 4 bonds and 0 lone pairs? o Tetrahedral, 109.5, sp3 - What is the molecular shape, angle, hybrid for 3 bonds and 1 lone pair? o Trigonal pyramidal, less than 109.5, sp3 - What is the molecular shape, angle, hybrid, for 2 bonds 2 lone pairs? o Bent, less than 109.5, sp3 - What is the definition of an Arrhenius base and acid? o Earliest definition describing classic strong base and acid - What are common strong Arrhenius acids? o H(halide) except for F, HNO3, HClO4, H2SO4 - What are common strong Arrhenius bases? o NaOH, KOH, LiOH - What are common weak Arrhenius acids? o Ch3COOH, HF, HNO2, H3PO4 - What are common weak Arrhenius bases? o Ba(OH)2, Ca(OH)2 - What is the definition of a bronsted base, bronsted acid? o Base accepts H+, acid donates H+ - What is the definition of a lewis acid and base? o An acid is a e acceptor, base is an electron donor. - What factors can indicate a lewis acid o Usually a cation or species with a 6 electron octet - What factors can indicate a lewis base o Has a lone pair, can be anion or neutral - What are common lewis acids? o H+, Zn+, CH3+, BF3, AlCl3 - What are common lewis bases? o NH2-, H-, OH-, CN- (these have an extra lone pair) - What does resonance provide to a molecule and how? o Stability, because they are low in energy - How can we evaluate the acidity quantitatively? o Pka - What is the definition and equation of pka? o –log ka, the desire to give up a protein - If the pka is less than 0 what is the acidity? Pka large? Pka small? o Strong, not acidic, acidic - What is the strength on an acid determined by? o The stability of its conjugate base - How does the size of an atom effect stability? o Larger atoms increases acidity - Why are larger atoms affected by size? o More stable as anions due to polarizability - What is polarizability? o The ability to spread charge across a space - How does the size of an atom affect bond strength o Larger the atom the weaker a bond it makes with H - How does electronegativity affect acidity? o Electronegativity increases acidity - Which has more of an effect on acidity, size or electronegativity? o Size - Does the presence of an electronegative atom affect another atoms acidity? o Presence of electronegative atoms near acidic h increases acidity - How does electronegative groups pull on e? o Inductively - What does inductively mean? o Charges transmittance through bonds without resonance - How does inductive effect act on stability? o Provides stability to conjugate base by spreading the charge - How does resonance effect acidity? How? o Increases acidity. Anion in resonance is stabilized. - What does equilibrium favor? o Formation of the weaker acid - How do you determine which acid is stronger? Which one does the big arrow go towards? o Compare pka of acid and conjugate acid. Arrow goes away from stronger acid. - How do you determine if something is effective at deprotonation? o Compare difference in pka between acid and conj. Acid. Pka> 2, effective. - What does a pka difference between acid and conj. Acid of 10 mean? o Irreversible deprotonation - What are the 3 steps in writing a condensed formula? o Work from left to right, find longest chain, list central atom, its h’s, then other groups in alphabetical order - What are parenthesis used for in writing condensed structure? o Branches go in parenthesis, and for repeated subunit with same type of c, and for symmetry (same group at the end of a chain) - How can you determine which chain is the main chain in bond line? o longest chain will be the main chain. - Where do substituents never go? o Inside the peak - What isn’t given parenthesis like (OH) in bond line? o Halogens - What are atomic orbitals? o 3D spaces where electrons are likely to be found, probability areas - What does a 1s orbital look like o Sphere - What does a 2s orbital look like? o Bigger sphere - What does a px orbital look like? How do you show different phases? o A dumbbell along the x axis, shade one side - What does a pz orbital look like? o Same as px, but along z orbital - What does py orbital look likes? o Same as px but along x orbital - What kind of bond is a covalent bond? o Sigma bond - What kind of bond is a formed from a single bond? How is it formed? o Sigma, formed by head on overlap of orbitals - What is stronger, sigma or pi? o Sigma - What happens to the phases in a sigma bond? o Two same phases combine to make new orbital, form a molecular orbital - If there is 4 bonding groups what is the hybridization? o Sp3 - How many pi and sigma bonds are in a double bone o 1 and 1 - S orbitals participate in what kind of bond? o Sigma bonds - P orbitals participate in what kind of bond? o Pi bonds - What kind of overlap does a sigma bond have/ o Head to head - What kind of overlap does a pi bond have/ o Side to side - Why are pi bonds weaker? o Side to side overlap is less of an overlap than head to head, therefore weaker - How many sigma and pi bonds are in a triple bond? o 1 sigma and 2 pi - What is a sp hybridized bond angle? o 180 - What is a sp2 hybridized bond angle? o 120 - What is a hydrocarbon? o Molecule made of h’s and c’s - What is the simplest and least reactive class of molecules we discuss? o Alkanes - What kind of hybridization do alkanes have/ o Sp3 - What kind of acid and base are alkanes? o Poor acid and poor base - How do you make a reaction occur in alkanes? o Have high temperature or high pressure - Alkanes are unsaturated/saturated? o Saturated - What does saturated mean? o Has maximum number of bonded h’s, no multiple bonds - What is the molecular formula for alkanes? o CnH2n+2 - List the names of alkanes 1-12 o Methane, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane - What are structural or constitutional iosmers? o Compounds with the same formula but the arrangement of the atoms is different. - What does an n-chain mean? o Straight chain, normal - What is the first step in IUPAC for branched alkanes o Find the main chain and give the number of carbons - What do you do if you have two carbon chains the same length when determining the main chain? o Use the one that has the most branches - What is the second step in IUPAC for branched alkanes? o Number the chain to give the lowest number to all substituents - What do you do if the numbers are the same for the substituents when determining the direction to number the main chain? o Lower number goes to the substituent that is first alphabetically. - What is the third step in IUPAC naming for branched alkanes? o Name the subs and give them their number. Turn alkane into a substituent by removing an H and replace ane with yl - What is the fourth step in IUPAC naming for branched alkanes? o List the substituents in alphabetical order followed by the main chain name - What is thie complex branch? o Isopropyl - What it this complex branch? o Tert-butyl - What is this complex branch? o Sec-butyl - What is this complex branch? o Isobutyl - What is the definition of conformations of alkanes? o Different arrangements formed about a single bond - What is a specific conformation called? o Conformer - What is a newman projection? o A perspective drawing looking down a single bond - What is a newman projection used for? o Conformational analysis - What is conformational analysis o Analyze differences in energy for different conformations - What is the general boiling point of alkanes? o Low compared to polar molecules of the same size - Which is stronger, dipole dipole or vanderwaals? o Dipole dipole - Which has a higher boiling point? Polar or nonpolar molecules? o Polar - How does surface area effect boiling point? o More c’s results in a higher b p due . - How does branching effect boiling point? o Branching decreases bp due to decreased surface area - How does melting point increase with imf strength? o Increases with increasing imf strength - How does surface area effect melting point? o Increases with increasing carbons - How does branching effect melting point? o Branches stack better, lead to crystalline structure, require more energy to melt, higher mp/ - What are cyclo alkanes? o Cyclic alkanes - What is the molecular formula for cyclo alkanes? o CnH(2n) - How do you name cyclo alkanes? o Cyclo+alkane name - What shape is cyclopropane? o Triangle - What shape is cyclobutane? o Square - What shape is cyclopentane? o Pentagon - When naming cycloalkanes what is the main chain? o The ring - How do you number cycloalkanes with one sub? o C1 is c with sub - How do you number cycloalkanes with two subs? o First sub that comes alphabetically is c1 - How do you number cycloalkanes with three subs? o Number so that subs have the lowest number possible. - How do you know if the cycloalkane is cis or trans/ o Cis has sub on same side, trans has opposite side subs - What is the ideal tetrahedral bond angle? o 109.5 - What kind of strain do cycloalkanes experience? o Ring strain - What is ring strain? o Strain associated with abnormal bond angles, torsional strain and steric strain - What is steric strain? o Crowding - Why is the strain on cyclopropane so high? o The H’s are eclipsed - Why is the strain of cyclobutane so high? o The H’s are almost eclipsed - Why does cyclopentane have a low strain? o It is not planar, assumes envelope formation - Why does cyclohexane have no strain? o The bond angle is perfect 109.5. assumes chain conformation. - What are the four classes of hydrocarbons? o Alkane, alkene, alkyne, arene (aromatic) - What is the general structure of alkane, alkene, alkyne, and arene? o Alkane has 1 bond between carbon, alkene has 2 bonds between the carbon, alkyne has 3 bonds between the carbons. Arene are in a ring. Can have o or n in ring. - What is the pka ranges for alkane, alkene, and alkyne? o 50-60, 42-49, 23-25 - What are the four characteristics of alkanes? o All c’s and H’s, all single bonds, unreactive, generally abbreviated as R - What are the 3 characteristics of alkenes? o All c’s and h’s contains at least one C-c double bond. Undergo electrophilic addition reactions - What are the 3 characteristics of alkyne? o All c’s and h’s. Contains at least one C-c triple bond. Undergo electrophilic addition reactions - What are the 2 characteristics of arene? o C and h’s sometimes n, o or s. undergo electrophilic and nucleophilic substitution - What are the 5 heteroatom’s? o Haloalkane, alcohol, ether, amine, ammonium ion. - Describe the general structures of the heteroatoms. o Haloalkane: r-x. Alochol: R-OH Ether: R-O-R. Amine R-Nh2. Ammonium ion: NH3+ - What are the pka’s of the heteroatoms? o Haloalkane, n/a. alcohol, 12-18. Ether, n/a. amine, 35-40. Ammonium ion 9-12. - What are the 3 characteristics of haloalkane? o Contain f, cl, br, or I. halogen abbreviated as X, undergo substitution and elimination reactions - What are the 3 characteristics of alcohols? o Undergo substitution and elimination, acid/base, and redox reactions. Reasonable nucleophile. Poor leaving group. - What are the two characteristics of ether? o Fairly unreactive except for under strongly acidic conditions. R’s don’t have to be the same. - What are the three characteristics of amine? o Good bases and nucleophiles, poor leaving groups, protonated amines are poor nucleophiles o - What are the two characteristics of ammonium ion? o Weak acids, not nucleophilic - What are the 5 carbonyls? o Ketone, aldehyde, carboxylic acid, ester, amide - What are the structures of keytone o Keytone is a c bonded to two r groups and double bonded to an o - What is the structure of aldehyde o An r and an H bonded to a c, o double bonded to the c - What is the structure of carboxylic acid? o Carbond bonded to an R, OH, and double bonded to O - What is the structure of ester? o Carbon bonded to an r and O, the O also Is bound to another R group. The carbon is double bonded to an O - What is the structure of amide? o Carbon bonded to an r, n and double bonded to an O. Coming off the N is either an H and R group or two R groups. - What is the pka of the carbonyls? o Ketone, n/a. aldehyde, n/a. carboxylic acid 3-5. Ester, n/a. amide, 15- 18. - What are the 2 characteristics of ketone? o C and O double bonded with two alkyl groups (r’s do not have to be the same), undergoes nucleophilic addition and reduction - What are the two characteristics of aldehyde? o C and o double bonded with an H on the C. undergoes nucleophilic addition and redox. - What are the three characteristics of ester? o C and o double bonded with an OH on the carbon. Moderate resonance observed. Nucleophilic and reduction reactions, r’s do not have to be the same - What are the three characteristics of amide? o C and o double bonded with an amine on the carbon (lots of resonance) nucleophilic and reduction reactions. R’s do not have to be the same. - What is the pka of HCl? o -8.0 - What is the pka of HBr? o -9.0 - What is the pka of H3o+ o -1.7 - What is the pka of NH4+? o 9.2 - What is the pka of H2O? 15.7
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