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This 13 page Study Guide was uploaded by lhall8 on Thursday December 17, 2015. The Study Guide belongs to Chem. 301 at Radford University taught by Professor Bibeau in Fall 2015. Since its upload, it has received 19 views. For similar materials see Organic Chemistry in Chemistry at Radford University.
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Date Created: 12/17/15
Chapter 1, Review of General Chemistry 1. Describe subatomic particles (relative mass, location, charge) 2. Write and interpret isotope notation 3. Write and interpret electron configurations and orbital diagrams 4. Describe cation and anion formation, including memorizing most common ions based on location on the periodic table (Al , O for example) 5. Differentiate ionic and covalent bonding 6. Draw appropriate Lewis structures, including selecting the best resonance structure. In order of priority: a. More octets (H, B, Al etc. are exceptions) b. More bonds c. Minimize formal charge and charge separation d. Place formal negative charges on more electronegative elements 7. Identify and describe polar bonds 8. Describe “net dipole moment” in a polar molecule, including the fact that a molecule may be nonpolar even if it has polar bonds if its dipoles cancel based on the shape of the molecule 9. Assign formal charges to atoms in molecules and polyatomic ions 10.Describe atomic orbitals, including shape, number and type of s,p,d,f 11.Describe the formation of molecular orbitals: sigma bonding (σ), sigma antibonding (σ *), pi bonding (π, pi antibonding (π ) 12.Describe hybrid orbital formation 2 3 13.Assign sp, sp , and sp hybridization to atoms based on their Lewis structures 14.Identify sigma and pi bonds in Lewis structures 15.Describe bond length and bond strength in Lewis structures 16.Identify the percent s character in an atom based on its hybridization 17.Relate amount of s character to bond strength and length and bond angle Chapter 2, Acids and Bases 1. Arrhenius vs. Bronsted-Lowry definitions 2. Reversibility of reactions at equilibrium 3. Defining acids, bases, conjugate acids, and conjugate bases, including relative strength (stronger parent acid = weaker conjugate base) and “nonbases” 4. Writing equilibrium expressions and K expressions a 5. Acid strength 6. Calculating pH, pOH, [H ], [OH ] - 7. Identifying structures of organic/carboxylic acids, and using resonance structures and delocalization of charge to explain acidity (pK a≅ 4) (tutorial on resonance structures in Chapter 8) 8. Identifying alcohols and describing their protic nature but lack of acidity in water (pK ≅ 16) a 9. Identifying amines and describing protic nature but lack of acidity (pK ≅ 35-a 40) 10.Identifying amines as bases and protonated amines as weak acids (pK ≅ 10) a 11.Identifying protonated alcohols and protonated carboxylic acids as strong acids (pK a -2, -6) about the same as H O 3 + 12.Describe how amines are amphoteric, though much better bases than acids 13.Predict the acid and the base in a pair of compounds, including strong and weak inorganic acids (HCl, HNO , H3SO 2 H 4O e2c.)3 carboxylic acids (RCOOH), protonated amines, (RNH ) water/alcohols (ROH), nonbases, 2 - deprotonated carboxylic acids (RCOO ), amines, (RNH ), dep2otonated alcohols/OH , deprotonated amines, RNH , hydride = H and carbanions 14.Predict the position of equilibrium based on the fact that equilibrium favors production of the weaker acid 15.Describe how electronegativity lowers pK by stabilizing negative charge in the conjugate base (stable bases are weak bases) 2 3 16.Describe how greater s character (sp > sp > sp ) lowers pK by stabalizing negative charge in conjugate base 17.Describe how electron-withdrawing substituents and closer proximity lowers pK aby inductive effects 18.Explain how increased size decreases pK by deaocalizing negative charge 19.Use the Henderson Hasselbalch equation to predict the pH of a buffer solution 20.Predicting charge of a species based on pH of surrounding solution and predicting whether the species will dissolve better in water or an organic solvent like ether (top layer) or dichloromethane (bottom layer) 21.Use the terms and predict compounds that are Lewis acids/electrophiles, Lewis bases/nucleophiles Chapter 3, Introduction to Organic Compounds 1. Identify acyclic alkanes and predict their molecular formula using C nH 2n+2 2. Name branched and straight-chain alkanes using IUPAC rules a. Identify the longest chain b. Number so as to give the lowest number to the first branch point c. Numerals (1,2,3…) show location and total number of numerals must match total number of substituents d. Prefixes (di,tri, tetra, are used when there are two or more of the same substituent) e. commas separate numerals from each other, dashes separate numerals from letters f. list substituents in alphabetical order 3. Identify and predict constitutional isomers 4. Use methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, phenyl, benzyl, vinyl 5. Identify primary, secondary, tertiary, and quaternary carbons 6. Identify cycloalkanes and predict their formula based on one index of unsaturation (2H) for every ring 7. Write and interpret line structures (skeletal structures) 8. Classify, identify, name, and describe the properties of alkyl halides, ethers, alcohols, amines, quaternary ammonium salts a. classify alcohols and alkyl halides as 1 ,2 ,3 o b. classify amines as 1 , 2 , 3o 9. Identify attractive forces (intermolecular forces = Van der waals, dipole- dipole, hydrogen bonds) in molecules and their effect on melting/boiling points and solubility 10.Describe how larger molecular surface area increases boiling point and how when two isomers are compared, the more branched isomer has smaller surface area (tennis ball vs. cigar) 11.Use hydrogen bonding to account for increased solubility in water and higher boiling points 12.Use the “like dissolves like” rule and to predict solubility and explain the molecular basis for this based on solute-solute, solvent-solvent, and solvent- solute interactions 13.Draw and interpret diagrams of solvation of molecules 14. Identify single bonds as capable of rotation but double-bonds as being “locked” 15. Sketch and interpret an energy diagram showing the conformations of ethane, butane, and other compounds with regard to rotation about the double bond 16.Explain and identify angle strain in cyclopropane and cyclobutane 17.Explain and identify torsional strain in cyclopropane and cyclobutane from eclipsing interactions 18.Recall that ring strain is a combination of angle and torsional strain 19.Draw and interpret chair conformations of substituted cyclohexanes, including axial and equatorial positions 20.Interconvert ring-flip conformations 21.Draw and interpret the energy diagram of substituted cyclohexanes 22.Identify and describe 1,3-diaxial interactions 23.Identify, describe, and draw cis and trans disubstituted cyclohexanes 24.Identify cis and trans decalins Chapter 4: Isomers 1. Recognize and define isomers, constitutional isomers (different connections between atoms), stereoisomers (same connections between atoms but different arrangement of atoms in space), enantiomers (mirror-image isomers, typically with asymmetric centers) diastereomers (geometric isomers (cis-trans isomers that result from restricted rotation because of rings or double bonds) 2. Identify cis-trans isomers in rings and across double bonds 3. Distinguish conformations (same molecule, rotation about a single bond) from different configurations (different molecules: stereoisomers of each other, typically) 4. Identify chiral objects 5. Identify asymmetric centers in molecules, including knowing that stereocenters are a broader category including both asymmetric centers and carbons in some double bonds 6. Recognizing enantiomers and their properties 7. Interpreting Fischer projections 8. Naming enantiomers and assigning R and S designations to asymmetric carbons/chiral centers 9. Describing how plane-polarized light is rotated by pure chiral compounds and by mixtures of enantiomers (see enantiomeric excess) 10.Describing racemic mixtures 11.Calculate enantiomeric excess 12.Defining and recognizing diastereomers 13.Recognize and identify meso compounds (contain asymmetric carbons but possess an internal mirror plane) all compounds with an internal mirror plane are achiral 14.Recognizing that the lone pair on a nitrogen can invert Chapter 5: Alkenes 1. Calculating degrees of unsaturation using the C Hn 2n+2rule a. -2H for every ring or pi bond (double bond =-2H, triple bond = -4 H) b. oxygen (and group 16) does not change the number of H’s c. halogens subtract 1 H (the –X is in place of an H) d. nitrogen (and group 15) adds and H to the count 2. Name alkenes, including dienes and cycloalkenes a. (find the longest chain with the double bond, give the start of the double bond the lowest possible number) b. Z vs E (Cahn-Ingold-Prelog priorities) and cis vs. trans (similar groups) 3. Identify vinyl and allyl positions 4. Identifying electrophiles and nucleophiles 5. Using curved arrow formalism to describe reactions a. nucleophiles are electron donors: curved arrow goes from electrons of nucleophile to electrophile + b. in acid-base reactions, arrows from electrons on the base toward H on acid, forming a new bond between the two 6. Interpreting and drawing energy diagrams/reaction coordinate diagrams, including a. endergonic vs. exergonic b. reactants, products, intermediates and transition states c. activation energy and adding a catalyst d. multistep reactions 7. Interpreting the Gibbs free energy equation 8. Calculating enthalpy by the bond energy method 9. Explaining how concentration, temperature, reactant order, and rate constant affect the rate of reaction Chapter 6: Reactions of alkenes 1. Write the mechanism of electrophilic addition reactions 2. Draw an energy diagram for electrophilic addition, showing carbocation formation as the slow step 3. Predict the most stable carbocation based on the order of carbocation stability (3 > 2 > 1 ) and that resonance stabilization increases stability 4. Apply the Hammond postulate to describe whether the structure of the transition state resembles the products or reactants 5. Predict the major product of electrophilic addition to an alkene based on carbocation stability (review from last test) 6. Predict and describe the mechanism of carbocation rearrangements 7. Predict the product of hydroboration/oxidation reactions and use the mechanism to explain why the predicted products are opposite that of traditional electrophilic additions of water 8. Predict the products and mechanism of electrophilic addition of Br 2and Cl 2 to an alkene 9. Predict the formation of halohydrins by adding alkenes to bromine water or chlorine water 10.Predict the product of epoxidation reactions of alkenes with MCPBA 11.Predict the products of ozonolysis of double bonds, including recognizing the structures of ketones and aldehydes 12.Predict the product of catalytic hydrogenation of a double bond 13.Order alkenes based on stability and magnitude of heat of hydrogenation 14.Distinguish stereospecific reactions from stereoselective reactions 15.Predict racemization at a chiral center and how it can lead to racemic mixtures (one chiral center) or 50:50 mixtures of diastereomers (more than one chiral center in the original molecule) 16.Predict products if two new chiral centers are created 17.Distinguish syn additions (catalytic hydrogenation, hydroboration, epoxidation) from anti additions (halohydrin formation, halogenation with Br 2) 18.Recognize that chiral molecules interact differently with each of a pair of enantiomers but achiral molecules interact the same Chapter 7 1. You do not need to memorize the priority of functional groups for this class, but you may have to interpret a name an write an appropriate structure 2. Describe the structure of the pi bonds in alkynes 3. Draw a mechanism for electrophilic addition of HX (X=Cl,Br etc.) to an alkyne, including addition of 2 molecules of HX to give a gem-dihalide and regioselectivity of terminal alkynes 4. Apply the relative stability of carbocations to predict products of electrophilic addition to alkynes. 5. Formation of pi-complexes will not be on the test 6. Write the mechanism and predict the products for acid-catalyzed addition of water to alkynes, including keto-enol tautomerism. Use of HgSO cat4lyst gives the same product as acid-catalyzed addition of water (follows Markovnikov’s rule). Note that terminal alkynes give ketones. 7. Write the mechanism and predict the products for hydroboration-oxidation (anti-Markovnikov) including keto-enol tautomerism. You will have to recognize 9-BBN and (Sia) B2 as borane reagents, but boron stoichiometry will not be tested. Note that terminal alkynes give aldehydes. 8. Recall the use of Lindlar’s catalyst to stop alkyne hydrogenation at the cis- alkene. 9. Recall the use of Li/NH t3 create the trans-alkene from an alkyne. No mechanism. 2 10.Recall the electronegativities and relative acidity of carbon atoms: sp > sp > sp (review from Ch 2) and recall relative but not absolute pKa values 11.Write the mechanism and predict the products of S 2 diNplacement by an alkyne anion on a primary halide 12.Predict the reactant conditions that will produce a given product using retrosynthesis Chapter 8 1. We will skip the history of benzene…please note that several of the slides are showing peoples’ MISTAKEN earlier view of what benzene was like 2. Draw resonance contributors for compounds that exhibit resonance using our guidelines, and interpret the meaning of resonance contributors (review), including identifying major resonance contributors 3. Recognize that more valid resonance structures contribute to greater stability by creating more delocalization of electrons 4. Describe how delocalization of electrons stabilizes compounds by reducing electrostatic repulsion of electrons 5. Apply the criteria for aromaticity to decide if a molecule is aromatic, antiaromatic, or nonaromatic a. planar molecule b. ring of uninterrupted electron density c. 4n + 2 electrons (an odd number of pairs of electrons= 2,6,10 etc. = aromatic) (4n electrons= even number of pairs of electrons, 4,8, 12 etc. = antiaromatic) d. nonaromatic = fails any of the above criteria 6. Recognize aromaticity in heterocycles, especially, pyridine, pyrrole, pyran, and thiophene including rehybridization of lone electron pairs and presence of non-bonding electrons in the nodal plane 7. Identify conjugated, isolated, and cumulated dienes and that only conjugated dienes benefit from delocalization 8. Describe pi systems using molecular orbital theory including 1,3-butadiene and aromatic systems 9. Predict relative heats of hydrogenation to use them to determine the stability of a compound 10.Recognize allyl and benzyl positions, that they benefit from resonance stabilization, and their relative stability compared with other carbocations 11.Use electron delocalization to predict the relative acidity of organic acids vs. alcohols (review) and phenol vs. other alcohols 12.Predict the relative lack of basicity in aniline 13.Describe electron withdrawing groups and electron-donating groups in aromatic systems 14.Predict the kinetic and thermodynamic products of addition of HX to 1,3- butadiene or similar systems 15.Explain the mechanism and how to favor production of either the kinetic or thermodynamic product 16.The proximity effect will not be tested 17.Write the mechanism for and predict the products of the Diels-Alder reaction, including stereochemistry and regiochemistry a. electron-withdrawing group favorable on the dieneophile b. electron-donating group favorable on the diene c. predicting the major product (1,2 or 1,4 not 1,3 on the ring in the product) d. using s-cis conformation Here’s a nice review I found. http://www.freelance-teacher.com/organic_chemistry_sn2_sn1_e2_e1.pdf Here are examples of the four mechanisms you’ll give on Test 4 SN2 mechanism example: Another example. Note inversion by backside attack. SN1mechanism example: http://www.wikipremed.com/03_organicmechanisms.php?mch_code=030204_030 Another example: E2 example: Strong base required. H and leaving group must be antiperiplanar, which is not obvious from the way this mechanism. Use a Newman projection if necessary. E1 example Note that the first step is the same asNS. Chapter 8 18.Write the mechanism for and predict the products of the Diels-Alder reaction, including stereochemistry and regiochemistry a. electron-withdrawing group favorable on the dieneophile b. electron-donating group favorable on the diene c. predicting the major product (1,2 or 1,4 not 1,3 on the ring in the product) d. using s-cis conformation Chapter 9 1. Recall the rate law for an SN2 mechanism and understanding why it implies that the mechanism is bimolecular 2. Give the energy diagram of an S N2 mechanism 3. Explain the relative rates in terms of steric interference to backside attack in S N2 4. Predict the product of S N with inversion of configuration by backside attack and write the mechanism 5. Describe steric interference to SN 2 attack that is remote from the leaving group (methyl > ethyl > neopentyl etc.) 6. Recall that weak bases are better leaving groups than strong bases 7. Explain nucleophilic strength a. The stronger the base, the better the nucleophile unless in protic solvents (though this can cause elimination side reactions) - i. negative charge beats neutral charge (OH better than H O) 2 ii. left on the periodic table beats right (N better than O) b. More polarizable = better nucleophile, so going down the periodic table makes for a better nucleophile (I better than Br ) 8. Polar aprotic solvents are best for SN2 reactions (DMF, DMSO, acetone) 9. Recall the rate law for an SN1 mechanism and why it implies that the reaction is unimolecular 10. Give the energy diagram of an S 1Nmechanism, with a slow first step 11.Predict the product(s) of an S N mechanism, including racemization, and give the mechanism 12.More inversion in S N mechanisms will not be on this test 13.Differentiate vinyl, allyl, phenyl (aryl), and benzyl positions and recall that vinyl and aryl positions CANNOT undergo S 1 oN S 2 rNaction Chapter 10 1. Give the mechanism and predict the product(s) of E2 reaction 2. Give the rate law of an E2 mechanism and explain how this implies this mechanism is bimolecular 3. Draw the energy diagram of an E2 reaction 4. Use alkene stability to predict regioselectivity in both E2 and E1 reactions (Zaitsev’s rule) 5. Explain how use of a bulky base can favor production of the less substituted alkene and predict the product of Hoffman E2 elimination 6. Give the rate law of the E1 mechanism and explain how this implies that this mechanism is unimolecular 7. Draw the energy diagram of an E1 reaction 8. Give the mechanism of an E1 reaction and predict the product by using alkene stability 9. Demonstrate that E2 reactions can only occur when the hydrogen and the leaving group are antiperiplanar to one another a. Convert a “wedge-dash” structure into a Newman projection, b. Next, rotate the Newman projection until the groups are anti- periplanar c. Finally predict whether the product is cis or trans based on this analysis NOTE: the book shows that an example with (2S,3S)-2-bromo-3-phenylbutane and (2S,3R)-2-bromo-3-phenylbutane . This is a good one to review 10.Predict the product of E2 elimination from six-membered rings 11.Predict whether elimination from a six-membered ring will be fast or slow depending on whether it occurs through a more stable or less stable conformer 12. Kinetic isotope effects are not on this test 13.Competition between E2 and S N2 will not be on this test 14.Recall that strong base is required for E2 mechanism to occur 15.Use the Williamson ether synthesis to make ethers from alkyl halides a. Use the S N mechanism to predict which reactions CANNOT occur (ex: t-butyl ethyl ether) 16.Use elimination reactions to form alkenes and alkynes Chapter 11 1. Recognize that strongly basic groups generally cannot act as leaving groups 2. Recall ways to make alkyl halides from alcohols (HX, PBr ,3PCl ,3SOCl 2 and tosylates from tosyl chloride (TsCl) 3. Give the S 2 displacement mechanism for reaction of an alkyl halide or N tosylate with a nucleophile (review from Ch 9 above) 4. Give the mechanism for acid-catalyzed dehydration of an alcohol (review from Ch 10 above) 5. Recall the use of POCl 3o dehydrate alcohols 6. Recall oxidation reactions of alcohols a. H 2rO o4 Na Cr2 in 4cid: primary alcohols to acid, secondary alcohol to ketone, tertiary alcohols cannot be oxidized b. pyridinium chlorochromate (PCC) can stop the oxidation of a primary alcohol at the aldehyde stage c. NaOCl (bleach) in acetic acid: primary alcohol to aldehyde (anhydrous conditions) secondary alcohol to ketone 7. Predict the product and give the mechanism of reaction of an ether with HX 8. Recall the use of peroxyacids like MCPBA and halohydrin formation followed by intramolecular S 2Ndisplacment to give epoxides 9. Predict the product and give the mechanism of epoxide opening (anti mechanism) in acidic and basic conditions, including regioselectivity 10.Explain that ring strain allows for the opening of epoxides in basic conditions despite the highly basic alkoxide leaving group 11.Synthesize trans-diols by epoxide opening and cis-diols by either (1. OsO 2. 4 H 2 2 H 2) or KMnO (co4d, dilute) 12.Recognize amines as common organic bases and give the mechanism for deprotonation by an amine 13.Give mechanisms for amines as nucleophiles (review of S 2/S 1 reactions) N N 14.Give the products of the Hoffman elimination of amines after treatment with methyl iodide and silver oxide 15.Recognize the structure of thiols Chapter 12 Covered in 302 Chapter 13 1. Draw mechanisms for and recognize the following types of reactions/steps in radical chain reactions: a. initiation = two new radicals formed from non radical b. propagation = one new radical formed from one old radical c. termination = two old radicals form a neutral molecule 2. Recall radical stability: tertiary > secondary > primary; allyl and benzyl stabilized by resonance. NOTE: vinyl and phenyl are NOT resonance stabilized! 3. Recognize bromination as more selective than chlorination because of the endothermic nature of the rate-limiting step 4. Recall that addition of HBr to a double bond gives the anti-Markovnikov product in the presence of peroxides 5. Recall that NBS is used for allylic/benzylic bromination 6. Predict the multiple products of allylic bromination by allyl shift Good Luck!
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