QuestionQuestion

Transcribed TextTranscribed Text

3. The pKa of phenol is 10, whereas that of p-hydroxyacetophenone is 8 (i.ep-hydroxyacetophenone is about 100 times more acidic as phenol). Draw all resonance structures for the two conjugate bases, and briefly explain the difference in pKa's for the two compounds. 4. Draw the reaction of cyclohexanecarboxamide with sodium hydride. Identify the acids on either side of the equation and compare their pKa values. Which side of the equation is favored? 5. Draw the reaction of sodium acetate with phenol. Identify the acids on either side of the equation and compare their pKa values. Which side of the equation is favored? 6. Draw the reaction of ethyl 3-oxobutanoate with sodium ethoxide. Identify the acids on either side of the equation and compare their pKa values. Which side of the equation is favored? 7. Draw the reaction of benzamide with sodium hydroxide. Identify the acids on either side of the equation and compare their pKa values. Which side of the equation is favored? 2 8. Identify the most acidic hydrogen in each molecule. Do this by redrawing the molecules in Kekulé form first (so you see how many there are), then identify the pKa's of all hydrogens. Circle the most acidio hydrogen in your Kekulé structure. O N O H N H NO2 9. Identify the most basic atom in the structures. OH CH3O O NH OCH3 OH H N N N NH N O H 3 12. Draw the products of the reaction of anisole with hydrochloric acid. 13. Draw the products of the reaction of 3-methoxybutan-2-ol with hydrochloric acid. 14. Draw the products of the reaction of acetophenone with hydrochloric acid. 4

Solution PreviewSolution Preview

These solutions may offer step-by-step problem-solving explanations or good writing examples that include modern styles of formatting and construction of bibliographies out of text citations and references. Students may use these solutions for personal skill-building and practice. Unethical use is strictly forbidden.

    By purchasing this solution you'll be able to access the following files:
    Solution.zip.

    $18.00
    for this solution

    or FREE if you
    register a new account!

    PayPal, G Pay, ApplePay, Amazon Pay, and all major credit cards accepted.

    Find A Tutor

    View available Organic Chemistry Tutors

    Get College Homework Help.

    Are you sure you don't want to upload any files?

    Fast tutor response requires as much info as possible.

    Decision:
    Upload a file
    Continue without uploading

    SUBMIT YOUR HOMEWORK
    We couldn't find that subject.
    Please select the best match from the list below.

    We'll send you an email right away. If it's not in your inbox, check your spam folder.

    • 1
    • 2
    • 3
    Live Chats