Show how you would synthesize each compound from benzene, toluene, or phenol using the following reactions:Reactions1. Halogenation2. Nitration3. Sulfonation4. Friedel-Crafts acylation5. Friedel-Crafts alkylation6. Oxidation of methyl group7. Reduction of nitro group• Choose the starting material from the drop-down list• Enter the number(s) of the desired reactions in the order that you wish to use them without commas between• If a reaction is used more than once, enter its number each time you wish to use itCompound 1: 5-chloro-2-methylbenzenesulfonic acidStarting material: tolueneReaction(s): 31Compound 2: m-bromobenzoic acidStarting material: [benzeneReaction(s):Submit AnswerTry Another Version1 item attempt remaining

Step 1: 1. Sulfonation (Reaction 3): Toluene can be sulfonated to form toluenesulfonic acid by…

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Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 7E: When toluene is treated with sulfuric and nitric acids under special conditions, three nitro (NO2)...

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When toluene is treated with sulfuric and nitric acids under special conditions, three nitro (NO2) groups are substituted for hydrogens at the 2, 4 and 6 positions on the ring (the next section discusses why the 2, 4, and 6 positions are substituted). The product is a highly explosive substance called 2,4,6-trinitrotoluene. This subastance is commonly known by a three letter name. What is it?
Several diamines are building blocks for the synthesis of pharmaceuticals and agro-chemicals. Show how both 1,3-propanediamine and 1,4-butanediamine can be prepared from acrylonitrile.
Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.
Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).
Draw the structure of the organic product formed when the given compounds undergo the three-step reaction sequence indicated. Select Draw Rings More Erase C Br 1. NaOC,H5. C,H5OH 2. NaOH, H2O 3. H3O*, heat
Acetals are formed from the reaction of two alcohols with a carbonyl under acidic conditions. Acetal formation is faster with 1,2-ethanediol than with two methanol molecules. Choose the factor that explains the difference in reaction rates. A) The reaction with 1,2-ethanediol has a lower AH (enthalpy) of reaction. B) The reaction with 1,2-ethanediol has a higher AH (enthalpy) of reaction. C) The reaction with 1,2-ethanediol has a more favorable entropy of reaction.
4. Synthesize the following compound. You may use benzene, acetylene, ethanol and any inorganic reagents. O₂N
7. Provide the major organic product of the following reaction sequence. 1. Mg 2. CO2 3. H,0*, A -Br
#16b. Provide the missing reactants, reagents, or products for the following reaction sequences below.
Starting with cyclohexanone, show how to prepare these compounds. In addition to the given starting material, use any other organic or inorganic reagents as necessary. a. Cyclohexanol b. Cyclohexene c. cis-1,2-Cyclohexanediol d. 1-Methylcyclohexanol e. 1-Methylcyclohexene f. 1-Phenylcyclohexanol g. 1-Phenylcyclohexene h. Cyclohexene oxide i. trans-1,2-Cyclohexanediol
Draw a structure for the major organic product you would expect from reaction of 3-methyl-3-pentanol with NaH.
e) sec-butyl bromide • Question 2: Identify the nucleophile and leaving group and draw the products of each reaction. a. b. Br + + OCH₂CH3 NaOH d. Br + N3 + NaCN

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