CH 220 1st EditionLecture 22- Recognize and be able to explain the difference between ionic and covalent bonds. - Be able to draw Lewis structures for compounds containing C, N, O, H, F, Cl, Br, and I.- Be able to explain the concept of hybridization, and recognize the type of hybridization in a given carbon center and the number of hybrid orbitals in a given structure.- Be able to explain what a polar covalent bond is, and be able to determine the direction of expected polarity for a given molecule. - Be able to identify constitutional (or structural isomers).- Be able to draw extended, condensed, and bond-line structures of alkanes and cycloalkanes.- Be able to recognize basic functional groups (all the functional groups in the worksheet I sentyou).- Using IUPAC rules, be able to name alkanes, haloalkanes, and cycloalkanes.- Be able to recognize and draw cis- and trans- isomers in disubstituted small ring systems(cycloalkane with two substituents).- Be able to draw and identify axial and equatorial substituents in cyclohexane and recognize thelower energy conformers in systems with more than one substituent.- Recognize alkenes and cycloalkenes and be able to name them using IUPAC nomenclature. - Recognize primary, secondary, and tertiary carbons.- Be able to name alkenes using the E/Z systemo Draw a line down the double bond and assess which of the bonds has the element with the highest atomic weight attachedo Both on “zee zame zide” - Be able to name alkyneso Any organic compound with a C-C triple bondo Same naming conventions as alkenes, but using a ‘-yne’ suffix- Be able to apply Markovnikov’s rule to the reactions of alkeneso Hydrohalogenation and Hydration use follow Markovnikov’s rule – the Hydrogen will always bond to the carbon with the most Hydrogen neighbors- Understand and be able to explain electrophilic addition reactions involving alkenes: o Addition of HX (hydrohalogenation) with mechanism Goes through a carbocation phase Markovnikov’s ruleo Addition of water to make alcohols (as a reversible reaction) Needs heat (250C) and a catalyst (H3PO4 or H2SO4) Vapor reactiono Addition of halogens (Cl-Cl and Br-Br) with mechanism Cannot use F (too explosive) or I (not reactive enough) Has a triangular intermediate – the Br or Cl gains the chargeo Addition of H2 Requires Pt, Pd, Ni or PtO2 and a solvent  Reaction doesn’t happen in a solution, but rather on the face of the catalyst Always results in a Cis configurationo Oxidation reactions (in acid as well as base, skip the epoxidation reaction). Hydroxylation- Adding of 2 x OH groups- Has a Syn mechanism, resulting in a Cis configuration- Needs a catalyst – KmnO4- Needs a base – NaOH- Needs a solvent – H2O- Results in a Vicinal Diol (neighboring OH) Oxidative cleavage - Breaks a molecule into two pieces (or in the case of a cyclohexane, will break the ring and create a straight chain molecule)- Needs a catalyst – KmnO4- Needs an acid- Needs a solvent - H2O - Understand and be able to explain the following reactions involving alkynes:o Triple bond must be in the parent chain and get the lowest numbero Has a linear structure, not cis or trans- Addition of HX (Hydrohalogenation)o Addition of HCl or other hydrohalogeno Goes through 2 reactions 1st equivalent – goes to a double bond (1:1 ratio of alkyne and hydrohalogen) 2nd equivalent – goes to a single bond (1:2 ratio of alkyne and hydrohalogentation) How far you take the reaction depends on what the required end product is- Halogenationo Addition of Br2 or Cl2o 1st equivalent (1:1) results in a double bond with a trans configurationo 2nd equivalent (1:2) results in a single bond- Hydrogenation o Initially goes to a double bond (Cis configuration)o Then goes to a single bondo For hydrohalogenation and halogenation, you are able to measure out the reactants in order to get a 1:1 or 1:2 reaction, but with hydrogenation, because there is a huge amount of H2 that is required to be pumped into the chamber, it is impossible to measure the reactants. Instead, a catalyst can be used in order to stop the reaction at the double bond, which has huge commercial value. This catalyst is Lindler Pd and it is a proprietary compound catalyst that stops the reaction at the double bond so that it doesn’t go any further.- Recognize aromatic compounds and be able to name them using current IUPAC nomenclature. o Monosubstituents – put name of substituent in front of Benzeneo Common names (make sure these are on the worksheet – can use in exam) These common names can be used as parent names in larger compounds: 2-bromotoluene- Understand and be able to predict the products of the following Electrophilic Aromatic Substitution reactions:The halogen can be Br2 or Cl2Needs a catalyst – FeBr3 or FeCl3Needs a catalyst – H2SO4Needs heatResults in benzenesulfonic acid and H2OUses an alkyl group attached to a Cl (has to be a Cl, no other halogen)The alkyl group could be any alkyl groupRequires a catalyst – AlCl3 (Friedel Craft Catalyst)Requires heatIt allows you to make a bond between two carbons, which has high commercial valueCarbonyl group reacts with benzene ring using AlCl3 (Friedel Craft Catalyst)Requires heat of at least 80 CThe carbonyl group is very reactive and so ‘opens the door’ for the reaction to happenKnown as functionalization – attaching a functional group in order to extendThe carbonyl group can be attached to any alkyl group - small or large- Understand and be able to explain which groups are ortho/para directors and which groups are meta directorso When asked to name IUPAC, use #s for substituents, for common use o-, m-, p-- Be able to synthesize simple benzene compounds, including substituted benzoic acid derivatives- Be able to explain the concept of chirality and recognize chiral centers (asymmetriccarbons, stereocenters) in a given compound.- Be able to recognize and differentiate enantiomers (stereoisomers that have the sameformula, the same connectivity, but different orientation in space, R/S).Uses priority system, like EZ1. Rank 4 different substituents by atomic number and build with model kit2. Hold the lowest priority substituent facing away from you and look at the remaining 3 groups on a plane3. If the priorities 1,2,3 are clockwise then it is designated R (right)4. If the priorities 1,2,3 are counter-clockwise then it is