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

385 Video Solutions

Write a bond-line formula for each of the following compounds: (l) Neopentyl alcohol

 

Watch Solution

Write a bond-line formula for each of the following compounds: (k) 1,4-Dicyclopropylhexane

 

Watch Solution

Write a bond-line formula for each of the following compounds: ( j) trans-4-Isobutylcyclohexanol

 

Watch Solution

Write a bond-line formula for each of the following compounds: (i) 4-Methyl-2-pentanol

 

Watch Solution

Write a bond-line formula for each of the following compounds: (h) trans-1,2-Dimethylcyclopropane

 

Watch Solution

Write a bond-line formula for each of the following compounds: (g) cis-1,2-Dimethylcyclopropane

 

Watch Solution

Formamide (HCONH2) has a pKa of approximately 25. Predict, based on the map of electrostatic potential for formamide shown here, which hydrogen atom(s) has this pKa value. Support your conclusion with arguments having to do with the electronic structure of formamide.

 

Watch Solution

As noted in Table 3.1, the pKa of acetone, CH3COCH3, is 19.2. 

(c) Write an equation for a reaction that could be used to synthesize CH3COCH2D.

Watch Solution

As noted in Table 3.1, the pKa of acetone, CH3COCH3, is 19.2. 

(b) Predict and draw the structure of the conjugate base of acetone and of any other contributing resonance form. 

Watch Solution

 As noted in Table 3.1, the pKa of acetone, CH3COCH3, is 19.2. 

(a) Draw the bond-line formula of acetone and of any other contributing resonance form.

Watch Solution

Dimethylformamide (DMF), HCON(CH3)2, is an example of a polar aprotic solvent, aprotic meaning it has no hydrogen atoms attached to highly electronegative atoms.

(c) DMF, when used as the reaction solvent, greatly enhances the reactivity of nucleophiles (e.g., CN- from sodium cyanide) in reactions like this: 

NaCN + CH3CH2Br → CH3CH2C≡N + NaBr

Suggest an explanation for this effect of DMF on the basis of Lewis acid–base considerations. (Hint: Although water or an alcohol solvates both cations and anions, DMF is only effective in solvating cations.) 

Watch Solution

Dimethylformamide (DMF), HCON(CH3)2, is an example of a polar aprotic solvent, aprotic meaning it has no hydrogen atoms attached to highly electronegative atoms.

(b) Draw what you predict to be its most important resonance forms [one is your answer to part (a)]. 

Watch Solution

Dimethylformamide (DMF), HCON(CH3)2, is an example of a polar aprotic solvent, aprotic meaning it has no hydrogen atoms attached to highly electronegative atoms.

(a) Draw its dash-type structural formula, showing unshared electron pairs.

Watch Solution

First, complete and balance each of the equations below. Then, choosing among ethanol, hexane, and liquid ammonia, state which (there may be more than one) might be suitable solvents for each of these reactions. Disregard the practical limitations that come from consideration of “like dissolves like” and base your answers only on relative acidities.

(b) NaNH2 + CH3C≡CH →

(The conjugate acid of this amine, aniline, has a pKa of 4.63.)

 

Watch Solution

First, complete and balance each of the equations below. Then, choosing among ethanol, hexane, and liquid ammonia, state which (there may be more than one) might be suitable solvents for each of these reactions. Disregard the practical limitations that come from consideration of “like dissolves like” and base your answers only on relative acidities.

(a) CH3(CH2)8OD + CH3(CH2)8Li →

Watch Solution

(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