7. Substitution reaction and mechanism. Please identify the product of the following reaction. Draw the arrow pushing mechanism to explain how the product forms (20 pts) OH Br (Heat) Mechanism: Product(s): OH
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- The following reaction can be described by a THREE step mechanism. A drawing of the energy diagram for this reaction is shown below. OH H, SO4 В A Reaction coordinate (i) Write out the three steps in this mechanism. For each step, draw structures for the reactants and products and curved arrows to show bonds formed and bonds broken. (ii) Indicate which of the drawings in your mechanism corresponds to points A, B and C on the energy diagram. Draw the structure of the MAJOR product in the following reaction and an arrow pushing reaction mechanism to showhow the product is formed. H;O+ Potential energy1. Predict the product and provide the mechanism for the following reversible nucleophilic addition. NaOH in H₂O 2. Predict the product and provide the mechanism for the following reversible nucleophilic addition. H2SO4 (cat) H EtOHAnswer the questions below with reference to the reaction shown here: Meo. `OH 2 Meo AICI3 (a) The reaction involves the initial formation of an "acylium ion" from 2: draw the mechanism for the formation of this ion. (b) Draw the structure of the intermediate formed when the acylium ion reacts with compound 1, and then show by means of curved arrows how this intermediate is transformed to the final product 3. (You do not need to show all the resonance forms of the intermediate.) Explain why the substitution takes place ortho to the OMe (c) substituent and not ortho to the methyl substituent.
- 1. Cl2, H20 2. NaOH Another mechanism for the formation of epoxides is through the formation of a chlorohydrin. Alkenes react with chlorine in the presence of H,0 to give a chlorohydrin via a cyclic chloronium ion intermediate. When the chlorohydrin is treated with strong base, HCl is eliminated and the epoxide is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing InstructionsWhat reaction category/mechanism type does the following reaction fit? O addition substitution (SN1) substitution (SN2) O elimination (E1) O elimination (E2) HCI CI + HOBr CH3OH + Br-Br H3CO The mechanism proceeds through a first cationic intermediate, intermediate 1. Nucleophilic attack leads to intermediate 2, which goes on to form the final product. In cases that involve a negatively charged nucleophile, the attack of the nucleophile leads directly to the product. +Br + CH3OH Br Intermediate 1 Intermediate 2 (product) In a similar fashion, draw intermediate 1 and intermediate 2 (final product) for the following reaction. OH + Br2 + HBr Br racemic mixture • Pay attention to the reactants, they may differ from the examples. In some reactions, one part of the molecule acts as the nucleophile. • You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate intermediate 1 and intermediate 2 using the → symbol from the dropdown menu.
- Determine a stepwise mechanism for the following reaction that illustrates why two substitution products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH) under Syl reaction conditions, even though it is a 1° alkyl halide. 1-bromohex-2-ene Part 1: Br CH₂OH The first step in the reaction proceeds according to which mechanism? CH₂CH₂CH₂CH=CHCH₂ + CH₂OH CH₂CH₂CH₂CH: Part 2: Br CHCH₂ Draw the missing resonance contributor. OCH3 + CH3CH₂CH₂CH=CHCH₂ CH3CH₂CH₂CH=CH-CH₂ + Br Br OCH 3 H₂CH₂CH₂CH=CH₂ view structure + + Br HBr XCan you show the steps to achieve the products and the mechanism? And can you see if the product is wrong?Draw the reactant of the following reaction sequence.
- 5. What is the major product of the following reactions? ( a) b) OH 2° OH Jones reagent H₂O HeatUse curved arrows to illustrate the stepwise mechanism for the following reaction. Show the intermediate after each step. ENSURE THAT YOUR MECHANISM IS KINETICALLY THE FASTESTThree reactions between a Grignard reagent and a carbonyl compound are given. Draw the main organic product for each reaction and indicate if H+ or H¯ is needed to complete each reaction. The starting material structures are provided in the answer fields as a starting point for your drawings. The first reaction involves a ketone. 1. CH₂MgBr 2. H+ or H™? Select Draw / |||||| C Rings O More Erase