Question

1. The pKa of salicylic acid is 2.97 whereas the pKa of benzoic acid is 4.19....

1. The pKa of salicylic acid is 2.97 whereas the pKa of benzoic acid is 4.19. Why is salicylic acid a much stronger acid compared to benzoic acid? (It is not enough to say “because the pKa is lower…”)

2. Draw a detailed mechanism for each of the two steps in the preparation of ethyl-3- coumarincarboxylate (2). You may assume that piperidine functions as a base and acetic acid serves as a proton source.

0 0
Add a comment Improve this question Transcribed image text
Answer #1

cooh COOH Salicydia benzoic aeid! oka = 2.97 acid pka = 4.19 intramolecular Coon o auth Hobonding + th Salicyclic acid ( 1 )

Add a comment
Know the answer?
Add Answer to:
1. The pKa of salicylic acid is 2.97 whereas the pKa of benzoic acid is 4.19....
Your Answer:

Post as a guest

Your Name:

What's your source?

Earn Coins

Coins can be redeemed for fabulous gifts.

Not the answer you're looking for? Ask your own homework help question. Our experts will answer your question WITHIN MINUTES for Free.
Similar Homework Help Questions
  • Organic chemistry -Carboxylic acid homework Question: In the general chemistry lab, students synthesize aspirin from salicylic...

    Organic chemistry -Carboxylic acid homework Question: In the general chemistry lab, students synthesize aspirin from salicylic acid and acetic anhydride. In the lab, students use sulfuric acid as a catalyst, but I want to consider an alternate method for synthesizing aspirin using sodium acetate as a catalyst: a. Draw the structure of sodium acetate. Is sodium acetate a stronger or weaker base than sodium hydroxide (NaOH). Explain. (1.5 pts) b. Consider the structure of salicylic acid. It contains two potentially...

  • 1. 2. Write an equation that describes what happens when benzoic acid (a solid) dissolves in...

    1. 2. Write an equation that describes what happens when benzoic acid (a solid) dissolves in water. Now write an equation that describes benzoic acid dissolving in diethyl ether (a liquid). (Hint: replace the (aq) phase symbol with (ether).) Write equations including pKa values that describes the following reactions: a. Acetic acid with aqueous NaOH. b. Ethyl amine with aqueous HCI. c. Phenol with aqueous NaOH. 2,6-dichloroindophenol (see in Part III) has a pKa value of 5.9 and is 10,000...

  • Experiment 12: Synthesis of Benzoic Acid pre-lab (4 pts) 1 (2 pts) Refer to the introduction...

    Experiment 12: Synthesis of Benzoic Acid pre-lab (4 pts) 1 (2 pts) Refer to the introduction on the general process of hydrolysis of nitriles to carboxylic acids. Starting with benzonitrile (shown below), show how it is converted to benzoic acid under basic conditions. N 2) (2 pts) The reaction for the synthesis of benzoic acid via benzonitrile hydrolysis is shown below: 1) NaOH, HO YOH + NaCl 2) HCI, H,0 Benzonitrile Density = 1.0 g/mL MM = 103.04 g/mol Benzoic...

  • can someone help me answer these 5 questions and figire this graph out please? Acid-Base Titration...

    can someone help me answer these 5 questions and figire this graph out please? Acid-Base Titration of a Weak Acid with a Strong Base: Determination of K. Introduction: You will be titrating a solution of a weak acid with 0.100 M NaOH, while monitoring the reaction using a pH meter. Weak acids have characteristic acid-ionization constants, K. The purpose of this lab is to use the titration to determine the value of this constant for the weak acid called “benzoic...

  • Exercise 2 Separation of a Mixture Based on Acid-Base Properties One purpose of this exercise is...

    Exercise 2 Separation of a Mixture Based on Acid-Base Properties One purpose of this exercise is to learn how to use a separatory funnel to extract a single component away from other compounds in solution. To do so, we will apply the principles of solubility and acid-base behavior you’re seeing in class. One of the compounds is neutral in the acid-base sense. It has no ability to either donate or accept a proton from an aqueous solution, and will remain...

  • I added everything thing. this is the lab question you need to solve. First assigned buffer...

    I added everything thing. this is the lab question you need to solve. First assigned buffer pH: 2.031 Second assigned buffer pH: 9.171 Available Buffer Systems (acid/ base) pka of Conjugate Acid 2.847 4.757 malonic acid/ monosodium malonate acetic acid/ sodium acetate ammonium chloride/ ammonia triethylammonium chloride/ triethylamine 9.244 10.715 1) Buffer system details: Given pH Name and volume conjugate acid Name and volume conjugate base 2) Calculations for preparation of high capacity buffer system. Introduction In this experiment, you...

  • 1. What is the definition of an 'equivalence point' in an acid/base titration? (1 point) 2....

    1. What is the definition of an 'equivalence point' in an acid/base titration? (1 point) 2. In part one of the experiment, you will prepare the acid solutions being titrated from a stock solution. Describe how you will accurately prepare 10.00 mL of 0.100 M HCl solution using a 1.00 M HCl stock solution. In your response to this question, be very specific about the quantities of stock solution and deionized water to be used in the dilution and the...

  • Give a detailed mechanism for this reaction and give a separation scheme NUCLEOPHILIC ACYL SUBSTITUTION: Synthesis...

    Give a detailed mechanism for this reaction and give a separation scheme NUCLEOPHILIC ACYL SUBSTITUTION: Synthesis of an Ester Isoamyl acetate (Banana Oil) Purpose This experiment demonstrat and alcohol. The technique of refluxing the reaction mixture is introduced. es the procedure for the synthesis of an ester from a carboxylic acid Esters are an important functional group in organic chemistry, and esters are found widely distributed in nature. Many lower molecular weight esters are associated with natural fuit flavors and...

  • Grignard reagent THE GRIGNARD REAGENT-PREPARATION AND REACTION In this experiment, you will prepa...

    i need help with the postlab questions please Grignard reagent THE GRIGNARD REAGENT-PREPARATION AND REACTION In this experiment, you will prepare a Grignard reagent, phenyl magnesium bromide, from bromobenzene and magnesium metal. The Grignard reagent will then react with methyl benzoate to form triphenylmethanol. Introduction Grignard reagents, such as organomagnesium halides, were discovered in 1910 by French chemist Victor Grignard. The Grignard reaction is one of the most general methods for carbon- carbon bond formation in all of organic chemistry....

  • 1. According to the paper, what does lactate dehydrogenase (LDH) do and what does it allow...

    1. According to the paper, what does lactate dehydrogenase (LDH) do and what does it allow to happen within the myofiber? (5 points) 2. According to the paper, what is the major disadvantage of relying on glycolysis during high-intensity exercise? (5 points) 3. Using Figure 1 in the paper, briefly describe the different sources of ATP production at 50% versus 90% AND explain whether you believe this depiction of ATP production applies to a Type IIX myofiber in a human....

ADVERTISEMENT
Free Homework Help App
Download From Google Play
Scan Your Homework
to Get Instant Free Answers
Need Online Homework Help?
Ask a Question
Get Answers For Free
Most questions answered within 3 hours.
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT