82,799 students have used Clutch for Orgo
97% got a better grade
3,804 minutes of Organic Chemistry videos

393 Video Solutions

(b) Rewrite the reaction sequence, showing all nonbonding electron pairs and using curved arrows to show electron pair movements.

Watch Solution

(a) Given the above sequence of reactions, draw structures for A through E.

Watch Solution

The compound at right has (for obvious reasons) been given the trivial name squaric acid. Squaric acid is a diprotic acid, with both protons being more acidic than acetic acid. In the dianion obtained after the loss of both protons, all of the carbon–carbon bonds are the same length as well as all of the carbon–oxygen bonds. Provide a resonance explanation for these observations.

Watch Solution

At 25°C the enthalpy change ΔH°, for the ionization of trichloroacetic acid is +6.3 kJ mol-1 and the entropy change ΔS°, is +0.0084 kJ mol-1 K-1. What is the pKa of trichloroacetic acid?

Watch Solution

The free-energy change, ΔG°, for the ionization of acid HA is 21 kJ mol-1 ; for acid HB it is -21 kJ mol-1 . Which is the stronger acid?

 

Watch Solution

Malonic acid, HO2CCH2CO2H, is a diprotic acid. The pKa for the loss of the first proton is 2.83; the pKa for the loss of the second proton is 5.69.

(a) Explain why malonic acid is a stronger acid than acetic acid (pKa = 4.75).

Watch Solution

Glycine is an amino acid that can be obtained from most proteins. In solution, glycine exists in equilibrium between two forms:

(a) Consult Table 3.1 and state which form is favored at equilibrium

 

Watch Solution

Supply the curved arrows necessary for the following reactions:

Watch Solution

Supply the curved arrows necessary for the following reactions:

Watch Solution

Supply the curved arrows necessary for the following reactions:

Watch Solution

Supply the curved arrows necessary for the following reactions:

Watch Solution

Supply the curved arrows necessary for the following reactions:

Watch Solution

Whereas H3PO4 is a triprotic acid, H3PO3 is a diprotic acid. Draw structures for these two acids that account for this difference in behavior.

Watch Solution

Arrange the following in order of increasing basicity:

(c) CH3CH=CH-, CH3CH2CH2-, CH3≡C-

Watch Solution

Arrange the following in order of increasing basicity:

(b) CH3O-, CH3NH-, CH3CH2-

Watch Solution

Arrange the following in order of increasing basicity:

(a) CH3NH2, CH3NH3+, CH3NH-

 

Watch Solution

Arrange the following compounds in order of decreasing acidity:

 

Watch Solution

Arrange the following compounds in order of decreasing acidity:

(b) CH3CH2CH2OH, CH3CH2CO2H, CH3CHClCO2H

Watch Solution

Arrange the following compounds in order of decreasing acidity:

(a) CH3CH=CH2, CH3CH2CH3, CH3C≡CH

Watch Solution

(b) Arrange the conjugate bases of the acids given in part

Watch Solution

(a) Arrange the following compounds in order of decreasing acidity and explain your answer: CH3CH2NH2, CH3CH2OH, and CH3CH2CH3.

Watch Solution

Starting with appropriate unlabeled organic compounds, show syntheses of each of the following:

Watch Solution

Starting with appropriate unlabeled organic compounds, show syntheses of each of the following:

Watch Solution

Starting with appropriate unlabeled organic compounds, show syntheses of each of the following:

Watch Solution

Acid HA has pKa = 20; acid HB has pKa = 10.

(a) Which is the stronger acid?

Watch Solution