5. For each of the following molecules, (i) state whether ortho-para or meta substitution will occur during electrophilic aromatic substitution and briefly (ii) justify your answer. a) b) LNO2 c) d) f) H. HS
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- a) The alkene drawn here undergoes an electrophilic addition reaction with HBr. Ś i) Give the IUPAC name of this molecule. ii) Outline the mechanism of this reaction. Your mechanism should show the formation of BOTH possible products and should also name both products. iii) Explain why the Markovnikov rule does not predict a major product in this case. b) The common name of the molecule drawn below is diisopropyl ether. Its structural formula is (CH3)2CHOH(CH3)2. tot It can be synthesized in two steps using the starting materials propan-2-ol, 2-chloropropane and sodium metal. One of these steps is a nucleophilic substitution reaction. i) Using structural formulae, write two balanced chemical equations representing the two steps of this synthesis. No state symbols are required. ii) Outline the mechanism of the nucleophilic substitution step.Two constitutionally distinct products are generated from the reaction of HBr with 1,3-butadiene. a) What type of reaction is indicated here? Utilize arrow pushing to indicate the mechanistic steps for this reaction. b) Draw hybridization orbitals on this molecule around the carbons for proper 3D geometry. Could you recognize any special situation occurring here? + H-Bra) Draw the ring-flip isomer of the molecule from question (b) Show which of the two is favored in the equilibrium between them, and explain why, showing all possible forms of strain in each of the isomers. (c) What is the stereochemical relationship between the two isomers? (d) Draw another stereoisomer of the molecule and show all the strains it contains.(strains is the most important one in this questuon!!!)
- Draw all possible C5H10 alkene isomers having a longest chain of four carbons and a methyl group. (Hint: Adapt the method described in Worked Example 12.12 to arrive at your answers.)Determine the relationship between the following pairs of compounds drawn below.Possible answers are listed in the box and can be used more than once, but each pair of structuresshould only have one answer each.1 and 2 _____3 and 4 _____5 and 6 _____7 and 8 _____A) constitutional (structural) isomersB) enantiomersC) diastereomersD) the same compoundE) unrelatedWhich of the following alkenes have the Z designation? Choose all that apply.
- 3) In the mid-1930s, the German theoretical chemist Erich Hückel developed a rule that dealt with the aromaticity of various compounds, which became known as the Hückel Rule. Which (parts) of the compounds listed below are aromatic? Justify your answer based on Hückel's rule. You can treat the rings separately or together as you wish.10B For the following compound determine the degree of alkyl substitution for the carbons indicated by arrows.ral compounds synthesized by flowers of the genus Chrysanthemum 15.81 Pyrethrins, such as jasmolin II (below), are a group of ne (known as pyrethrum flowers) to act as insecticides. (a) Circle and name the functional groups in jasmolin II. (b) What is the hybridization of the numbered carbons? (c) Which, if any, of the numbered carbons are chiral centers? CH3 CH2=CH-CH, 3. 4 CH-C-O-HC5 C-C-O-CH3 CH3-C H,C-C CH3
- Which of the following is the most accurate depiction of a structure at the point shown on the energy diagram below? (Hint: Consider the Hammond Postulate) Reaction Coordinate (A) (B) (C) (D) A В O D Energy1) a until gII) Reactions - Complete the following reactions by drawing clear structures for the major organic product, reagent, or reactant. Remember stereochemistry (where applicable)! a) b) d) Notes on inputting answers in boxes: If the answer is a single compound, give its structure clearly. If the answer is a racemic mixture, you may give one enantiomer's structure clearly and write "racemic" or (+) under the answer. If the answer is a mixture of diastereomers, you must clearly give the individual structure of each product. . 1. NaH 2. Na, NH3 structure 1) F3C OOH 2) FeCl3, (1 equiv) H₂N. xs H₂, Pd/C 1) (sia)₂BH 2) H₂O2, NaOH H₂O 1. Cy₂BH 2. H₂O2, NaOH, H₂O FeCl3 (1 equiv)