Dihydroxylation Practice Problems

Show suitable reagents to carry out the below-given conversion.

trans-But-2-ene to (d,l)-butane-2,3-diol

Show suitable reagents to carry out the below-given conversion.

cis-but-2-ene to meso-butane-2,3-diol

What is (are) the expected product(s) of the given reaction?  Specify the relative stereochemistry of the outcome. If a racemic mixture is formed, draw both of the enantiomers.

Give the expected product(s) of the given reaction and identify its relative stereochemistry. If a racemic mixture is produced, draw both of the enantiomers.

Give the product(s) formed when the given molecule reacts with  OsO₄, followed by NaHSO₃, H₂O.

Determine the product(s) formed when the given molecule reacts with (1) OsO ₄ and then with (2) NaHSO₃.

What is(are) the reagent(s) needed for the following reaction?

What is(are) the reagent(s) needed for (4R,5S)-1-isopropyl-4,5-dimethylcyclohex-1-ene to form (1S,2S,4R,5S)-1-isopropyl-4,5-dimethylcyclohexane-1,2-diol?

A different number of pericyclic reactions was previously studied. Draw the arrow-pushing mechanism of the following reaction.

Determine which of the given organic compounds would give a positive permanganate test in a cold solution. (Recall that a positive permanganate test turns the KMnO₄ solution from purple to brown.)

Determine the substrate and the reactants needed to form the given alcohol.

Determine the product(s) for the given reaction below.

Indicate the stereochemistry, and draw both enantiomers if the product is a racemic mixture.

What is the product for the given reaction below?

Why, when utilizing a terminal alkene, is it not required to display the relative stereochemical outcome of the product in the reaction below?

Draw the reaction intermediates and major products for the following reactions.
Show the stereochemistry where applicable.

Show the complete reaction for the formation of the given molecule, starting with a suitable cyclic alkene.

Show how you would convert hex-3-enedioic acid to 3,4-dihydroxyhexanedioic acid.

Show the complete reaction for the formation of the given molecule, starting with a suitable cyclic alkene.

What are the major products formed during the reactions given below? Also, provide their stereochemistry where appropriate.

a. cycloheptene + KMnO₄/H₂O (cold, dilute)
b. cycloheptene + peroxyacetic acid in diethyl ether, followed by H₂O/H⁺

(a) Propose a mechanism for epoxidation and acid-catalyzed ring opening of trans-hex-3-ene.

(b) Predict the final product for the reaction of cis-hex-3-ene under the same conditions.

What is the expected product of the following reaction?

What are the major products formed during the reactions given below? Also, provide their stereochemistry where appropriate.

a. cis-hex-3-ene + OsO₄/H₂O₂
b. cis-hex-3-ene + peroxyacetic acid, followed by H⁺, H₂O

Draw the reaction intermediates and major products for the following reactions.
Show the stereochemistry where applicable.

Draw the reaction intermediates and major products for the following reactions. Show the stereochemistry where applicable.

Draw and name the products of the cis-dihydroxylation of the molecules shown below.

Provide the mechanisms that produce the two enantiomers in the following reaction.

Determine which would give a positive permanganate test from the molecules given below. A positive result would turn the potassium permanganate solution from purple to brown.



What is(are) the product(s) of the reaction? Draw both enantiomers if the product is a racemic mixture.

Provide the product(s) formed in the reaction of the alkene with each reagent:

What are the products that will be formed from the following reaction conditions?

Show the products that will form when the following alkene reacts as follows:

Draw the arrows to show the mechanism for parts (i)–(iv) in the given sequence.

Which of the molecules below is expected to give a positive result to the permanganate test?

NMM is discarded as a by-product in the process shown below. Propose a solution to make the catalytic cycle more sustainable while still using NMO as the co-oxidant.