The reaction between propionyl chloride and acetate ion is outlined below. a) Complete the mechanism of the forward reaction by placing curved arrows to show the electron movements in the reactants and intermediate product. i: :0: b) Draw the structures of the final product and leaving group, including any charges. (Electrons may be omitted.) 1L
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- Question 5. (20 points) Consider the following reaction. + PhLi (2 eq.) then water a) Propose a structure for the final product. b) Give a complete mechanism for the transformation. c) Draw an energy diagram of the transformation and briefly comment on the relative energies of the starting material, final product, and any intermediate(s), and about the rate determining step.5. Each of the following may participate in an elimination reaction, under the proper conditions. (a) Circle the alpha (a) carbon. (b) Circle the beta (B) carbon(s). (c) Draw the alkene product(s) that may form, with the new double bond between the a and B positions. (d) If more than one alkene product is possible, circle the most stable (Zaitsev) product. X tx + 33) Use the reaction shown below and the associated reaction energy diagram to answer the following questions. E A Но- + Br HO. Br- reaction coordinate a) In the space above, use curved arrows to show the mechanism of the reaction. b) Classify the reaction as either addition, elimination or substitution. c) In this reaction is hydroxide (HO-) acting as a nucleophile or as a base? c) Based on the reaction energy diagram, is the reaction endergonic or exergonic? d) Based on the reaction energy diagram, and assuming the reaction is reversible, would the equilibrium lie to the left or to the right? e) Which position on the reaction energy diagram (A, B or C) corresponds to the transition state?
- Q3. For the substitution reactions below, draw out the reactions as shown and answer the following questions for each example: (i) Draw the structure of the unknown product(s) of the reaction. (ii) Identify the nucleophile, electrophile and the leaving group for each step. (iii) Identify each mechanism as Sn1 or SN2. (iv) Insert curly arrows to represent the reaction mechanism. с. Na Product EThank you for your help on this (a-c)a) Draw the structure of alkene and proposed reagent(s) used to prepare the product in Reaction A. Draw the reaction mechanism for first image b) Predict the molecular structure of the major product(s) of Reaction B and C with second image c) Rank the following compounds from the lowest to highest boiling point. Explain your answer briefly. A: 1-Butanoic acid; B: 1- Butanol; C: 1-Butane d) Draw any three alcohol isomers with molecular formula of C4H10O. e) Based on isomer structures you drawn in part (d), draw the final oxidation product(s) (by KMnO4/H+) of any two isomer, respectively.
- 4. The rearrangement reaction shown below was discovered in 1860. (a) Draw a mechanism for this transformation. Draw in lone pairs, use curved arrows to show movement of electrons, and indicate the formal charge on all charged atoms. (b) Explain why this rearrangement occurs. (Hint: What type of intermediate forms?) но он H2SO4 (conc.) Heat (c) The same type of reaction was used to accomplish the transformation below. Draw the mechanism for this transformation as well. OH H2SO4, heat ноQuestion 1. But-1-ene can be converted to but-2-ene in two steps (reactions A and B), or it may be reacted with bromine in diethyl ether (reaction C): Conc. HCI A в Bra Etg0 ? (a) Draw a curly arrow mechanism for reaction A. Identify the nucleophile and electrophile in each step. (b) Draw a diagram showing relative energy against reaction progress for your mechanism in part (i), indicating the positions of all organic species observed in the mechanism. (c) What type of reaction is reaction B? (d) Propose a reagent that could be used to convert but-1-ene to but-2-ene in a single synthetic step, and give a curly arrow mechanism for the reaction. (e) Predict the product(s) and give a mechanism for reaction C. Explain the stereochemical outcome of the reaction.QUESTION 6 6) Select a FALSE statement about the SN2 & E2 mechanisms for the reaction between an Alkyl Halide (RX) reactant and an anionic reagent that could act as Nucleophile (Nu") or Bronsted Base (B): A) There is NO involvement of reactive intermediates in either mechanism. B) E2 mechanism involves simultaneous loss of the halide and loss of a B-proton in one step C) SN2 mechanism involves stereospecific attack of nucleophile from the opposite side of the leaving group D) Both mechanisms have the SAME type of rate equation rate = k [RX] 4 O A OB ос OD 2 pa 2
- For esch of the following two reactions draw the major product. Br,, hv KMNO, heat4) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors, the regiochemistry that results in each case. ỌMe Na, MeOH ? NH3 CHO Na, MeOH ? NH34. Explain in terms of bonding why ethene mostly undergoes electrophilic addition reactions. Draw the mechanism for the reaction of but-1-ene and hydrogen bromide. Show, via the mechanisms that are two different possible isomers - explain which one is formed preferentially and why this occurs. Mechanism 1 Mechanism 2 Equation (reactants and products) – reaction 1 Equation (reactants and products) – reaction 2 Major product Minor product