Devise the most efficient synthesis for the carboxylic acid below using a starting material and reagents from the tables. Give your route by specifying the number of the startingmaterial followed by the letters of the reagents you would use beginning with the first step.The answer 4fh means treat t-butanol(4) with conc. HCl(f) then treat the product with KOH in alcohol(h).Starting materialsReagentsOHBrBrOHH₁CLOHBriHO+a Mg / dry ethere Aqueous H2SO4 at refluxi KMnO4/H3O+b 1. CO₂ 2. acidic workupf Conc. HCI or HCI (gas)j Na₂ CrO4 / aqueous H2SO4c NaCN/THF or DMFg PBr3k 1. BH/THF 2. H₂O₂/aq. NaOHd NaCN/dil. aqueous H2SO4h KOH / alcoholThe most efficient synthetic route isSubmit AnswerRetry Entire Group2 more group attempts remaining

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Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Propose a strategy for the given synthesis.
Starting with benzene and using any other reagents of your choice, design a synthesis for the following compound: COOH NO₂ COOH The target molecule above can be prepared by treating benzene with some reagent or combination of the reagents listed below. Give the necessary reagents 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 Mel, AlCl3 B KMnO4, NaOH, heat (followed by H3O+ workup) C HCI, Zn D E F (CH3)2CHCI, AICI 3 HNO3, H2SO4 Fuming H2SO4
From the table of available reagents select the one(s) you would use to convert butanoic acid to each of the following products: (Use the minimum number of steps; from one to six are required. List reagents by letter in the order that they are used; example: fa. NOTE: Assume that a normal aqueous (or mild acid) workup follows each reaction; you do not need to add reagents for the workup.) Reagents Available a. benzene/AlCl3 d. H₂O, H₂SO4 b. (CH3)2CuLi e. H₂, Pd/C c. CH3NH₂ f. K* -OC(CH3)3 1-bromobutane butanenitrile g. LiAlH4 h. NaCN i. NH3 j. PBr3 k. Dess-Martin periodinane I. SOCI₂
organolithium reagents are strong bases. Because of this, they cannot be prepared from compounds that contain acidic groups (-OH, -NH:, -NHR, -SH, -C=CH, RCO:H) or compounds that have carbonyl groups. Which of the given syntheses of a Grignard reagent below would fail to form as written? Circle the answer and explain your choice Br Mg, ether MgBr 1) Mg, ether Mgl 2) Br Mg. ether MgBr 3) но но 2. Predict the major products for the following reactions with the correct stereochemistry were necessary. SOCI, LOH OH OH SOCI NBS ight NBS G light Me (CH, Cel Br MgBr
Draw compound A and B and identify reagents 1,2 and 3
Design two syntheses of the compound below using the Wittig reagent and a carbonyl compound. Show all reagents and intermediates . Of the two , which is the better synthesis . Explain your reasoning
2. Propose a reasonable mechanism for the following reactions. Label each reagent's role in the reaction. Assume aqueous work up to obtain neutral products. b. Ar- HO OH Ar ZnCl₂ Ar Hint: ZnCl₂ is a Lewis Acid.
12. Provide a pathway to make the given carboxylic acid from the given starting material. Give all the reagents and write out the reactions. Show mechanism. OH & Br OH COOH
4. Synthesis Using the carbon-containing starting material(s), propose a synthesis by drawing structures for all intermediates. The carbon atoms in the product must originate from the starting material(s) (or a carbene/carbenoid or CO2), but you may use as many equivalents of each starting material as you would like, and any reagent/reaction you know. (note: no mechanisms are required). OH
Make a systematic process for the synthesis of the benzene derivative from benzene. Present all the needed reagent and reaction conditions and products. (Note the electron-donating or electron- withdrawing) NH2
Starting from acetylene, propose a synthesis for the following compound. Use any other organic or inorganic reagents as needed. HO.
H₂C OEt H₂C OEt 1. NaOEt, EtOH 2. H₂O* H₂C EtOH OEt Esters, like aldehydes and ketones, are weakly acidic. Treatment of an ester with 1 equivalent of a strong base, such as sodium ethoxide, causes a reversible carbonyl condensation to occur that forms a ẞ-ketoester. This reaction is known as the Claisen condensation. The tetrahedral intermediate thus formed expels an alkoxide leaving group to give an acyl substitution product, a ẞ-ketoester. The steps leading up to this point are all reversible. The best yields for the Claisen condensation are obtained when the starting ester has more than one acidic a-hydrogen. In these cases, a second deprotonation of the a-carbon drives the reaction equilibrium toward the product, thus requiring a full equivalent of base instead of a catalytic amount. Subsequent protonation with dilute aqueous acid resultsn a high yield of the final product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing…

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