Below is the final step in a synthesis of a widely used anxiolytic (anti-anxiety) drug. Give the product of this reaction, and the full, step-by-step mechanism for its formation. (You don't have to draw the whole molecule in every step, just the parts that are actually changing). Y N CI cat acid (HOTS) NH2 remove Ho O Ph
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- Mechanism: A reaction mechanism for the following reaction is shown below. H+ CEN CEN: N-H || -C-OH H₂O, H* Step 1 wand woled mot ozsm E Step 3 N-H C-OH C=N-H Step2 C=N-H H-O-H H₂O motno vgiene fesrigid onlt to smotnos -C=N-H a) The overall reaction is an example of b) Step 1 is c) Step 3 is d) Draw in the curved arrows for each step. e) Identify the nucleophiles and electrophiles where appropriate. f) Fill in the reaction energy diagram. H₂O: rate determining step to noipojovo hamwell sit 5(emise erit voittons 10) vanas mi sdgin al rainW di of E^ reaction progress →How many acid-base steps occur in this mechanism? :OH fö OH ₂ H CI: -H₂O (C5H12O) (CsH3O*) :CI: :CI:- yox (C5H1*) (C5H₁1CI)4. Outline a detailed mechanism for the reaction below. Identify the abbreviation for the reaction mechanism. НО H3PO4
- OH OH ∞∞ BF3 Et₂O This reaction takes place via a pinacol rerrangement. Please, draw curved arrows to show the movement of electrons in this SPECIFIC step of the reaction mechanism. +BF3 HO: :OH OH (BF3OH)Consider the following overall reaction, which will be discussed in Chapter 20. H,C-CEN NH3 HOO H,C Below is a proposed mechanism for this reaction. Use the rules we learned in this chapter to evaluate whether each step in the proposed mechanism is reasonable. For each step that is not reasonable, explain why. :ÖH () H,C-CEN: H3C OH OH (i) + H,C H3C OH OH (ii) H,C H,C OH (iv) + H,O: H,C H,C OH (v) H3C H3C OH H. (vi) :NH, NH. H,C H,CA set of three nucleophilic displacement reactions is shown below: - Br -Br -Br "CHз Hзс CHз C В A NaCN CH-он SN2 reaction Which reaction (A, B, or C) proceeds the fastest? Which reaction (A, B, or C) proceeds the slowest?
- 3. The following three SNAR transformations follow different mechanisms. Draw an intermediate or transition state for each reaction that relates the correct mechanism. Write a short sentence as to why that is the correct intermediate for the reaction. Reaction 1: Reaction 2: NO2 NO2 NO₂ + NaOMe NO2 + NaOH2 1. aq NaHCO3. 100 C 2. H₂O+ OMe NO2 NO₂ OH ŇO₂ NO2 Reaction 3: CFa Br CF3 8--2 + NaNH2 NH3 NH₂ Intermediate/transition state Intermediate/transition state Intermediate/transition stateThe accepted mechanism for a rearrangement reaction is shown below. "Q Ph (1) (ii) Ph Ph HO™ fast Ph Ph HO O™ slow Ph aufae .Ar² LOH HO™ fast Draw a curly arrow mechanism for this transformation. Sketch an energy profile for this reaction, showing approximate relative energies for the reactants, intermediates, transition states, and products. HQ Ph (iii) When DO™ was used as the reagent, the rate of product formation was same as for HO™. Explain why this result shows that the third step is fast and cannot be rate-determining. Ph (iv) Write the predicted rate equation for this mechanism, and show how it was derived. (v) The starting diketone may have two different aryl groups, as shown below. Propose a ¹³℃ labelling experiment that would allow you to distinguish which of the two aryl groups had migrated in this situation. OH AR²0- Ar¹ C CIdentify the most likely intermediate in the mechanism leading to the product. НО НО НО. НО OH OH OH OH eTextbook and Media НО НО. Но OH OH _ОН НО. OH
- Describe the mechanism of the following reaction. 1) H2N NH2 (excess) SH SH `CO2H AcO 2) КОН 3) H +Minoxidil is a molecule that causes hair growth in some people. It was originally synthesized as a vasodilator for the treatment of hypertension (high blood pressure). Most of the patients taking the drug for hypertension were seen to grow body hair. Due to other side effects, its oral use was stopped, but it became popular as a topical cream to promote hair growth. NH2 N-OH NH Minoxidil The first key reaction in one synthesis of minoxidil follows. Draw the product of this reaction. NH NC.In the following reactions, for each letter below. (1) predict whether the reaction will undergo (SN1, SN2, E1, E2 or no reaction) (2) predict the major product after the reaction (write the name of the product: Do not draw) Br Eto (a) EIOH, 50 °C Br (b) t-BUOK t-BuOH, 50 °C (c) (d) (e) Br Br t-Bu. MeO MeOH, 50 °C t-BUOK t-BuOH, 50 °C r acetone, 50 "C