1. (20 points) Design two syntheses of the compound below using the Grignard reagent and a carbonyl compound. Show all reagents and intermediates. Of the two, which is the better synthesis. Explain your reasoning.

2. (a) Mark the alpha carbons with "a" and draw out the alpha hydrogens (if any are present). (b) If enolizable, draw a mechanism and the enolate product below. Use B: as a generic base. H₂N

2.1) Draw the structure of "major organic final product" of the following Addition of H₂O to alkyne reaction. The chemical structure must have the correct number of carbon atoms and functional group(s) to earn points. H3C-C=CH 1. (Sia)₂BH.THF 2. OH, H₂O2 Problem viewing the image. Click Here 2.2) Draw the structure of the "enol intermediate". 2.3) Draw the step-by-step curved arrow pushing mechanism of Tautomerization from "the enol intermediate to the major organic final product" under Base-Catalyzed condition. Your answer must include all related resonance contributors, and all lone pair electrons must be included in your drawing.

Fill in the appropriate reagents to achieve the synthetic transformation shown below. Note: If one or more reagents are incorrectly placed, a single red X will appear on the top left. 1. он 2. 3. 4. 5. PCC, DCM Br(CH2)2CH3 benzylamine CH3(CH2)2MGB NABH3CN, cat. H*, cyclohexylamine acetone H3O* NaOH NazCr207, H20, H2SO4 cyclohexylbromide

4. Design a synthetic scheme using any reagents and reactions that have been discussed in CHEM2402. Only reactions and reagents from CHEM2402 will be considered. a) i) ii) E iv) i) ii) Br Br = b) Design a synthetic scheme using the reagents given for the following two reactions. All reagents are used for each reaction scheme and in each case, a reagent can be used more than once. Take the necessary time to complete this question. 2 eq. Br 2 eq. Br Хо OCH3 H₂/Lindlar's catalyst Br₂/CH₂Cl₂ so NaH H3O+/H₂O H₂/ Lindlar's catalyst PCC/CH₂Cl₂ NaH H3O+/H₂O CH₂Br

A. Using acetylene as your only source of carbon atoms, design a synthesis of pentanal, shown below (Note: pentanal has an odd number of carbon atoms, while acetylene has an even number of carbon atoms): i The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B C 1) O3; 2) DMS 1) R₂BH; 2) H₂O₂, NaOH NaNH, D E F H₂, Lindlar's cat. 1-bromopentane H₂. Pt G H 1-bromobutane H2SO4, H₂O. HgSO4 EtBr D. Proposa Propose an efficient synthesis for the following transformation. The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just…

Please help with step-by-step mechanism for fundemental claisen

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5. Propose a synthesis of each of the following compounds using the indicated starting material. You may use any organic compounds, inorganic compounds, organometallic compounds, or solvents of your choice. Do not show any reactive intermediates, mechanisms, or transition states, but be sure to show each isolable compound along your synthetic route. a. b. C. Ph + PPh3 Cl mylom Ph. CH3 steps steps steps H3C. H3C Ph CH3 CH3 Ph OH ÕH Ph (racemic) 4

Answer as a string of capital letters