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Home , Resonance (chemistry)

Organic 1- Review Resource

Hi everyone congrats on making it through the last full week of classes! I hope these resources have been helpful in navigating through this tough class. Here is link to find the resources if you want to go back and review these topics in depth and for practice problems! https://www.baylor.edu/support_programs/index.php?id=967950

Also, don't forget that we have one more group tutoring session this semester, tuesday at 5:30 pm! here is the link to sign up. https://www.baylor.edu/support_programs/index.php?id=40917

Formal Charge: • = (How many electrons does it want) – (how many electrons does it have)

Resonance (week 3 resource): http://leah4sci.com/resonance-structures-organic-chemistry- tutorial-video/ • Golden rules for drawing resonance structures 1. Avoid breaking single bonds 2. Never exceed an octet for a second row element 3. Pay attention to charges in resonance structures- they can move around

• Resonance patterns: https://www.youtube.com/watch?v=9B5FGPDwX_E

Acids and Bases (week 4 resource): • Evaluating acidity quantitatively: using pKa Values o The smaller the pKa value, the more acidic the proton o Evaluating Equilibrium using pKa values: Equilibrium will ALWAYS favor the weaker acid • Evaluating acidity of protons qualitatively: Looking at stability of conjugate o What if we are asked to determine the relative acidity of protons, but we do not know the pKa values?? We have to compare the stability of the conjugate bases! § THE MORE STABLE THE CONJUGATE BASE, THE MORE ACIDIC THE PROTON o How can you determine the stability conjugate bases? o Use the acronym ARIO A: the atomic bearing charge R: Resonance stabilization I: Induction O: Orbital

Nomenclature (week 4): Step 1 for naming alkanes: • Find longest continuous carbon chain- in red (what is left over is called a - in green) Step 2: name the Main chain: use the table above • If carbons are in a ring, root name is cylo+root+ane (cyclooctane) Step 3: • name the • Use the root names in the table but with a suffix of -yl • Halogen substituents are named like chloro, bromo, fluoro etc. Step 4: • number the main chain • Numbering rules: 1. Start numbering at one end 2. Start numbering on the side that gives the substituents the lowest numbers possible 3. if there is a tie with substituents go to next substituent

Stereochemistry (week 5): https://www.khanacademy.org/science/organic- chemistry/stereochemistry-topic/diastereomers-meso-compounds/v/stereoisomers- enantiomers-diastereomers-constitutional--and-meso-compounds • Enantiomer: a compound that is one of a pair of non-superimposable mirror image isomers https://www.khanacademy.org/science/organic-chemistry/stereochemistry- topic/optical-activity/v/rs-system-new?modal=1 o It is a relationship between two • Fischer projections: Drawings show the configurations of chiral centers using a cross instead a wedge and dash drawing. https://www.khanacademy.org/science/organic- chemistry/stereochemistry-topic/optical-activity/v/fischer-projection- introduction?modal=1 o Everything vertical is behind the plane o Everything horizontal is in front of the plane • Symmetry and meso compounds: https://www.khanacademy.org/science/organic- chemistry/stereochemistry-topic/diastereomers-meso-compounds/v/meso- compounds-new-july?modal=1

Nucleophiles (week 6): • Nucleo= nucleus (they have a positive charge), Phile= likes..... so, a nucleophile is something that likes the positive nucleus of atoms. • https://www.khanacademy.org/science/organic-chemistry/substitution-elimination- reactions/sn1-sn2-tutorial/v/nucleophile-electrophile-and-the-schwartz-rules Electrophiles (week 6): • Electro= electron (they have a negative charge), Phile= likes..... so, an electrophile is something that likes negative charges

Substitution Reactions (week8): • SN2 o Kinetics: § Rate=k[substrate][nucleophile]oSterically hindered electrophiles react slower: § Primary substrates are favored for SN2 o Stereospecifity § https://www.youtube.com/watch?v=QxIUeYAQRy0 o Core steps: § Loss of leaving group § Nucleophilic attack

• SN1 o Kinetics: k=[electrophile] § Tertiary substrates are favored o Stereochemistry o https://www.youtube.com/watch?v=jUEzjS0IFxs o Core steps: § Proton transfer § Loss of leaving group § rearrangement § Nucleophilic attack § proton transfer

Elimination Reactions (week 9): • stability: o More substituted is more stable • E2: o Kinetics: § Rate= [substrate][base] § Tertiary substrate favored § Concerted o Regioselectivity https://www.khanacademy.org/science/organic- chemistry/substitution-elimination-reactions/e1-e2-tutorial/v/e2-elimination- regioselectivity § More substituted product is favored o Stereoselctivity https://www.khanacademy.org/science/organic- chemistry/substitution-elimination-reactions/e1-e2-tutorial/v/e2-elimination- stereoselectivity o Stereospecificity https://www.khanacademy.org/science/organic- chemistry/substitution-elimination-reactions/e1-e2-tutorial/v/e2-elimination- stereospecificity • E1: o Kinetics: § Rate= [substrate] § Stepwise § Tertiary substrate preferred o Regioselectivity § More substituted favored o Stereoselectivity: https://www.khanacademy.org/science/organic- chemistry/substitution-elimination-reactions/e1-e2-tutorial/v/e1-mechanism- stereoselectivity § Trans is favored o Carbocation rearrangements § https://www.khanacademy.org/science/organic-chemistry/substitution- elimination-reactions/e1-e2-tutorial/v/-and-rearrangements Substitution v Elimination (week 9): • https://www.khanacademy.org/science/organic-chemistry/substitution-elimination- reactions/sn1-sn2-e1-e2-jay/v/elimination-vs-substitution-reagent

Addition Reactions of • Hydrohalogenation: https://www.khanacademy.org/science/organic- chemistry/alkenes-alkynes/alkene-reactions-tutorial/v/hydrohalogenation?modal=1 • Acid catalyzed hydration: https://www.khanacademy.org/science/organic- chemistry/alkenes-alkynes/alkene-reactions/v/addition-of-water-acid-catalyzed- mechanism • Oxymercuration Demercuration: • Hydroboration Oxidation: https://www.khanacademy.org/science/organic- chemistry/alkenes-alkynes/alkene-reactions-tutorial/v/hydroboration-oxidation- mechanism?modal=1 • Catalytic • Halogenation: https://www.khanacademy.org/science/organic-chemistry/alkenes- alkynes/alkene-reactions-tutorial/v/halogenation?modal=1 • Halohydrin: https://www.khanacademy.org/science/organic-chemistry/alkenes- alkynes/alkene-reactions-tutorial/v/halohydrin-formation?modal=1 • Anti-dihydroxylation • Syn-dihydroxylation: https://www.khanacademy.org/science/organic- chemistry/alkenes-alkynes/alkene-reactions-tutorial/v/syn-dihydroxylation?modal=1 • Oxidative cleavage

Addition reactions of alkynes (week 10): • Catalytic hydrogenation • Reduction with Lindlar’s catalyst • Dissolved metal reaction o https://www.khanacademy.org/science/organic-chemistry/alkenes- alkynes/alkyne-reactions/v/reduction-of-alkynes?modal=1 • Hydrohalogenation of alkynes https://www.khanacademy.org/science/organic- chemistry/alkenes-alkynes/alkyne-reactions/v/hydrohalogenation-of- alkynes?modal=1 • Hydration of Alkynes https://www.khanacademy.org/science/organic- chemistry/alkenes-alkynes/alkyne-reactions/v/hydration-of-alkynes?modal=1 • Hydroboration Oxidation https://www.khanacademy.org/science/organic- chemistry/alkenes-alkynes/alkyne-reactions/v/hydroboration-oxidation-of- alkynes?modal=1 • Halogenation of alkynes • Ozonolysis of alkynes o https://www.khanacademy.org/science/organic-chemistry/alkenes- alkynes/alkyne-reactions/v/halogenation-and-ozonolysis-of-alkynes?modal=1 • of terminal acetylides (adding to another alkyl group