QUESTION 4. (a) Below are two structural isomers. Interestingly, one of these structures is significantly more acidic than the other. Circle the most acidic proton in each. Determine which structure is more acidic and explain why. Use your knowledge of resonance structures and molecular geometry to support raumont

QUESTION 4. (a) Below are two structural isomers. Interestingly, one of these structures is significantly more acidic than the other. Circle the most acidic proton in each. Determine which structure is more acidic and explain why. Use your knowledge of resonance structures and molecular geometry to support raumont

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter5: Resonance

Section: Chapter Questions

Problem 2CTQ: You will not find “hydroxide” in the stockroom, but you will find sodium hydroxide (NaOH)...

See similar textbooks

Similar questions

3. For the following acid - base reaction, (a) predict the products; (b) identify the Bronsted acid, Bronsted base, conjugate acid, and conjugate base; (c) use curved arrows to show the flow of electron pairs in the reaction. CH3 CH2C-OH + NaNHa
Practice q # 4 4. Which nitrogen in this molecule is the most basic? Explain briefly your choice. (3) H₂N. (4) H₂N. (2) O (1) HN
Why is it not possible to predict whether H3PO4 or H2SO3 is the stronger acid? Show how you can use data to decide which is the stronger acid.
4. Given the following: NaOH (c) H₂O The Lewis Acid(s) is(are) (b) NaOH (c) H₂O (d) NH3 & b (f) a &c g Oh a (a) BF3 (b) (d) NH3 Of (g) b & c (a) BF3 (e) a (h) a-c (i) a-d
For each conjugate acid-base pair, identify the first species as an acid or a base and the second species as its conjugate acid or base. In addition, draw Lewis structures for each species, showing all valence electrons and any formal charge. (a) CH3S- CH3SH
Salicylic acid, HOC6H4CO2H, and its derivatives have been used as pain relievers for a long time. Salicylic acid occurs in small amounts in the leaves, bark, and roots of some vegetation (most notably historically in the barkof the willow tree). Extracts of these plants have been used as medications for centuries. The acid was first isolated in the laboratory in 1838.(a) Both functional groups of salicylic acid ionize in water, with Ka = 1.0 × 10−3 for the—CO2H group and 4.2 × 10−13 for the −OH group. What is the pH of a saturated solution of the acid (solubility = 1.8 g/L).(b) Aspirin was discovered as a result of efforts to produce a derivative of salicylic acid that would not be irritating to the stomach lining. Aspirin is acetylsalicylic acid, CH3CO2C6H4CO2H. The −CO2H functional group is stillpresent, but its acidity is reduced, Ka = 3.0 × 10−4. What is the pH of a solution of aspirin with the same concentration as a saturated solution of salicylic acid (See Part a).(c) Under some…
Part 2 of 2 Draw the skeletal structure of the product(s) for the Lewis acid-base reaction. Include lone pairs and formal charges (if applicable) on the structures. The Click and drag to start drawing a structure.
Write the reaction as proton-transfer reactions. Label which reactant is the acid and which is the base, which product is the conjugate base of the original acid, and which is the conjugate acid of the original base. In addition, write Lewis structures for each reactant and product and use curved arrows to show the flow of electrons in each reaction.
(2) 1a. Fix the following structure which is a neutral molecule. You cannot add atoms. H H—C—C—N H (2) 1b. Clearly indicate any lone pair electrons that need to be present. This may be shown on the diagram above. (2) 1c. Clearly indicate the direction of the bond dipole for the C-N bond. This may be shown on the diagram above. (4) 1d. Draw the conjugate base for the structure. (2) 1e. Show how resonance stabilizes the conjugate base. This may be shown on the diagram above. (2) 1f. Draw the conjugate acid.
4. A student has prepared 0.05 M solution of CH3-C=CH and has added to it 0.05 M solution of potassium tert-butoxide (K" O-C(CH3)3). (i) Write the equation for the acid-base reaction that might occur. (ii) With curved arrows track the movements of electron pairs. (iii) Assign Base, Acid, Conjugate acid for the base, Conjugate base for the acid. (iv) Calculate the percentage of deprotonated methyl acetylene taking into account that pKa of the conjugate acid of potassium tert-butoxide equals 18 and pKa of methyl acetylene equals 24.
Compare with explanation the acidity of the following pairs of compounds. (Note: You must draw the appropriate resonance structures to support your answers.) (c) (i) .COOH .COOH H3CO
Consider the molecular models shown here, where X representsa halogen atom. (a) If X is the same atom in bothmolecules, which molecule will be more acidic? (b) Doesthe acidity of each molecule increase or decrease as theelectronegativity of the atom X increases?