Organic Chemistry
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What is the appropriate product of the following oxidation reaction?
Every oxidation involves a reduction. Determine the atom that underwent reduction in the final step of the following Swern oxidation mechanism.
Determine the aromatic product formed by oxidizing the given molecule with an excess of the oxidizing agent PCC.
Why can acyclic trans-diols be cleaved using metaperiodic acid but not cyclic trans-diols?
Draw the compound generated by the Dess-Martin oxidation reaction below.
Draw the product that would form when the following hemiacetal undergoes Dess-Martin oxidation.
The lactone below is produced by oxidation of the phenol derivative. Provide an arrow-pushing mechanism for the reaction.
Explain why tertiary alcohols cannot be oxidized under chromic acid oxidation.
Identify the product of the given oxidation reaction.
Determine the product of the oxidative cleavage given below.
When the following optically active molecule is oxidized using the Swern oxidation, the product is found to be optically inactive. Provide a suitable reason for this observation.
Draw the major product in the reaction given below.
Draw a suitable mechanism for the reaction of propan-2-ol with dimethylchlorosulfonium ion which is produced as an intermediate during the Swern oxidation.
Show the expected products by the reaction of the following compound with the reagents given below.
a. PCC (pyridinium chlorochromate)b. sodium hypochlorite/acetic acidc. chromic acid
Draw the structures of the products when the following compounds react with each of the reagents given below.
Compounds:
a. butan-1-ol
b. butan-2-ol
Reagents:
(1) DMP
(2) Na2Cr2O7/H2SO4
(3) 1 equivalent NaOCl-TEMPO.
(4) PCC
Give the major products expected from the following reactions.a. butan-1-ol + DMSO + oxalyl chlorideb. sodium ethoxide + 3-bromo-3-methylpentane + heatc. 2-cyclohexylpropan-1-ol + DMP reagent
Predict the major products expected from the given reactionCyclopentanone + Tollens reagent
Predict the major products expected from the given reaction.Cyclopentanecarbaldehyde + Tollens reagent
Identify which of the following compounds can give a positive Tollens test.a. CH3COCH3b. CH3CH2CHOc. CH3CH2CH=CHCH=CHOH
What are the expected products when each of the following compounds reacts separately with PCC and chromic acid?
a. Cycloheptanol
b. 1-methylcycloheptanol
c. Cyclohexyl methanol
Tertiary alcohols are resistant to oxidation. Nonetheless, allylic tertiary alcohols can undergo oxidation through an allylic shift, as shown below. The reagent used for this reaction is called a Bobbitt's reagent.
Show the products of the following reactions using Bobbit's reagent.
Many oxidizing agents have multi-valent atoms. This atom goes from a higher oxidation state to a lower oxidation state during oxidizing an alcohol.Show the oxidation states of the given atoms in their oxidized and reduced states using their Lewis structures.a. the Os atom in OsO4b. the Cr atom in PCCc. the ring nitrogen in Bobbitt's reagent
When two unknown compounds A and B with the molecular formula C3H6O, were subjected to different chemical tests, the following results were obtained.Propose the structure for these two compounds.
Show the products formed by the cleavage of the following compounds using periodic acid.
What is the correct product of the oxidation reaction shown below?
Identify the correct product of the oxidation reaction given below.
Give the correct product of the oxidation reaction shown below.
Give the correct mechanism for the oxidation reaction shown below:
Using chromic acid, a chemist attempted to convert a primary alcohol to a carboxylic acid. The shown product was obtained as a major component of the mixture.
Does the following arrow-pushing mechanism account for the formation of the product?
What is the correct mechanism for the oxidation reaction given below?
Provide the missing product in the oxidation reaction shown below:
True or False: When a ketone is in equilibrium with its hydrated form, it can be further oxidized to a carboxylic acid. Justify your answer.
Although NMO is introduced as a solution to a green chemistry problem, it still poses a risk as it creates additional problems. What is the problem, and how might it be solved?
Which alcohol undergoes oxidation to yield the carbonyl compound shown below?
Provide the missing reagent for the oxidation reaction shown below.
Determine the product(s) that would form when the starting organic compound is subjected to the given condition(s). If no reaction occurs, write "NR".
Give the products that will form when the following molecule is allowed to react with (i) PCC, and (ii) H2CrO4, H2O.
Determine the products that will result when the molecule below reacts with the following reagents: (i) HOCl, H2O, and (ii) HIO4. Write "N.R." if no reaction occurs.
Shown below is the arrow-pushing mechanism of the Swern oxidation reaction. Encircle/box/highlight the individual step representing the general mechanism for all alcohol oxidation reactions.
Draw the mechanism of the oxidation reaction given below.
What is the mechanism of the oxidation reaction given below?
Instead of oxidizing 5-methylbenzene-1,3-diol into m-quinone, the following reaction synthesized the three products below. Draw the mechanism for the synthesis of each product.
Determine the product(s) that would form when the starting compound is allowed to react with PCC and H2CrO4, H2O. Write "NR" if there is no reaction.
Provide the mechanism of the oxidation reaction given below.
Determine the product(s) that would result when the starting compound is allowed to react with HOCl/H2O and HIO4. Write "NR" if there is no reaction.
Give the product(s) that would result when the starting molecule is subjected to the given conditions. Write “NR” if there is no reaction.
Draw the product(s) that would form when the starting molecule is subjected to the given conditions. Write “NR” if there is no reaction.
Determine the product of the oxidation of the given alcohol under the following conditions: (a) PCC and (b) H2CrO4, H2O. If there are no reactions, write "NR."
What are the products of the reaction of the given alcohol with (a) HOCl, H2O, and (b) HIO4? If there are no reactions, write "No Reaction."
Draw the product(s) that would form when the starting organic compound is subjected to the given reaction condition(s). If no reaction occurs, write "NR".
Bisphenols can be oxidized to quinones.
For the reaction shown,
(i) Determine the oxidation numbers of C-1 and C-2 from reactant to product.
(ii) Draw the arrow-pushing mechanism.
i) Explain why the molecule below is not oxidized to a meta-quinone.
ii) What is the actual expected product of the oxidation?
Determine the correct product of the following oxidation reaction.
Without water, the aldehyde below cannot be oxidized to a carboxylic acid. True or False?
In the treatment of industrial wastewater, one process involves the addition of isopropanol to mitigate the toxicity of certain heavy metals. How might isopropanol contribute to decreasing the concentration of manganese(VII) in the water?
Which alcohol would undergo oxidation to yield the carbonyl compound shown below?
Determine the alcohol that undergoes oxidation to yield the carbonyl compound below.
Draw the product of the oxidation reaction given below.
Determine the product formed when each of the following alcohols reacts with H2CrO4:
(i) octan-3-ol
(ii) octan-1-ol
(iii) 3-methyloctan-3-ol
Give the products formed when the alcohols listed below undergo Swern oxidation:
(i) 7-methyloctan-3-ol
(ii) 7-methyloctan-1-ol
(iii) 3,7-dimethyloctan-3-ol
Propose the plausible major product that would be synthesized from the given reaction below.
For the following compounds.
Which compound would result in a positive Tollens test? [Keep in mind that mild basic aqueous conditions are necessary for the Tollens test]
What are the product(s) formed from the reaction of HIO4 with the following?
The reaction below has a mechanism that resembles that of pinacol rearrangement. Show its mechanism and explain which part is similar to the pinacol rearrangement.
Draw the products formed from the reaction of 3-hydroxyoctanal with (1) Na2Cr2O7/H2SO4 and (2) PCC
Draw the product formed from the reaction of 4-hydroxyoctanal with (1) DMP and (2) 1 equiv NaOCl-TEMPO
Show the structures that could result from the reactions given below.
(1) cycloheptanol + NaOCl/HOAC
(2) cyclohexylmethanol + CrO3・pyridine・HCl
Draw the major products resulting from the reactions given below. Provide stereochemistry if necessary.
(i) cyclohexylmethanol + Na2Cr2O7/H2SO4
(ii) cyclohexanol + HCl/ZnCl2
(iii) propan-1-ol + HBr
What product will be formed when cyclopentanone reacts with each of the following reagents?
(i) H2CrO4 or NaOCl (excess) with CH3COOH
(ii) PCC or NaOCl (1 equiv.) with TEMPO
What product will be formed when cyclopentane reacts with each of the following reagents?
What product will be formed when 1-phenylethan-1-ol reacts with each of the following reagents?
What is/are the product/s of the reaction of 1-cyclopentylcyclohexane-1,4-diol with
(1) 1 equiv NaOCl-TEMPO and (2) DMP?
What is/are the product/s that could form from the reaction of 1-ethylcyclohexane-1,4-diol with (1) Na2Cr2O7/H2SO4 and (2) PCC?
Tertiary alcohols are resistant to oxidation. Nonetheless, allylic tertiary alcohols can undergo oxidation through allylic shift, as shown below. The reagent used for this reaction is called a Bobbitt's reagent.
Show the products expected to form when the following compounds are oxidized using Bobbitt's reagent.
Draw the major product formed in the reaction given below.
What is/are the product/s of the oxidation of the starting material below using the following reagents (in excess)?
(i) DMP (periodinane) reagent
(ii) DMSO and oxalyl chloride
Ethanol is given as an antidote for methanol poisoning because it acts as a competitive inhibitor of methanol to ADH enzyme. A chronic alcoholic typically needs a higher dose of ethanol compared to a nonalcoholic. Explain why this increased dosage of the competitive inhibitor is necessary for someone with a history of heavy alcohol consumption.
Show how you would convert 2-methylcyclohexan-1-ol to the following compounds (ignore stereochemistry).
(a) 1-methylcyclohex-1-ene
(b) 2-methylcyclohexyl 4-methylbenzenesulfonate
(c) 2-methylcyclohexan-1-one
Show how you would synthesize each of the following compounds starting with an appropriate alcohol.
Draw the structures of (1) through (3) in the following scheme. Ignore stereochemistry.
Draw the major product of the reaction shown below:
Give the major product formed from the reaction shown below.
The oxidation of alcohols by chromic acid involves two steps: forming a chromate ester and eliminating H+ and chromium. Which step is likely to be rate-limiting?
Furthermore, kinetic studies have shown that compound I oxidizes much slower than compound II when subjected to chromic acid oxidation. Rationalize the difference in reactivities.
Predict the products of the reactions of (i) propan-1-ol and (ii) propanal with:
(a) chromic acid or excess sodium hypochlorite with propionic acid,
(b) PCC or NaOCl (1 equiv.) with TEMPO.
For each reaction in the sequence below, write the correct reagent:
For each reaction in the following sequence, write the suitable reagent:
Lipoamide is an intermediate of the TCA cycle and is found attached to some proteins.
a. Is lipoamide a weak reducing agent or a weak oxidizing agent? Show the structures of its reduced and oxidized forms.b. Show how lipoamide combines with pyruvic acid (2-oxopropanoic acid) to form acetyl lipoamide.c. Complete the equation given below to show the oxidation of an aldehyde by lipoamide.
Provide the alcohol reactant for the oxidation reaction below.
Provide the reagent for the oxidation reaction below:
Draw the alcohol(s) that would produce the given ketone upon oxidation.
Write the necessary reagents for the following reaction.
Provide the reactant(s) required to complete the synthesis shown below.
Show how the following synthesis can be carried out:
Use any reagents necessary.
Show how the following synthesis can be carried out using the given starting material and any suitable reagents.