CHEM 2021 — Final Exam

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Last updated 4:58 AM on 8/12/26

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19 Terms

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What are the different reactions that only produce aldehydes?

Oxidation reaction w/ DMP
DIBAL-H reaction

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) of the oxidation reaction of 1° alcohols with DMP?

Starting Material: 1° alcohol

Reagents: DMP/Dess-Martin Periodinane (oxidizing agent), CH₂Cl₂ (solvent)

Product: Aldehyde

<p><span style="color: red;"><strong>Starting Material:</strong></span> 1° alcohol </p><p><span style="color: blue;"><strong>Reagents:</strong></span> DMP/Dess-Martin Periodinane (oxidizing agent), CH<sub>2</sub>Cl<sub>2</sub> (solvent)</p><p><span style="color: purple;"><strong>Product:</strong></span> Aldehyde</p>

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) of the reductive reaction with DIBAL-H?

Starting Material: Ester

Reagents:

DIBAL-H (reducing agent), Toluene (solvent)
H₃O⁺ (acid-workup step)

Conditions: -78°C (dry-ice temperature)

Product: Aldehyde

<p><span style="color: red;"><strong>Starting Material:</strong></span> Ester</p><p><span style="color: blue;"><strong>Reagents:</strong></span> </p><ol><li><p>DIBAL-H (reducing agent), Toluene (solvent)</p></li><li><p>H<sub>3</sub>O<sup>+</sup> (acid-workup step)</p></li></ol><p><span style="color: green;"><strong>Conditions:</strong></span> -78°C (dry-ice temperature)</p><p><span style="color: purple;"><strong>Product:</strong></span> Aldehyde</p>

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What are the different reactions that only produce ketones?

Oxidation reaction of 2° alcohols w/ DMP
Oxidation reaction of 2° alcohols w/ KMnO₄
Oxidation reaction of 2° alcohols w/ CrO₃
Oxidation reaction of 2° alcohols w/ Na₂Cr₂O₇
Friedel-Crafts Acylation
Hydration of Alkynes w/ HgSO₄
Acid chloride and Gilman Reagent Reaction
Grignard Addition to a Nitrile

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) of the oxidation reaction of 2° alcohols w/ DMP?

Starting Material: 2° alcohol

Reagents: DMP/Dess-Martin Periodinane (oxidizing agent), CH₂Cl₂ (solvent)

Product: Ketone

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) of the oxidation reaction of 2° alcohols w/ KMnO₄?

Starting Material: 2° alcohol

Reagents: KMnO₄ (oxidizing agent), H₂O, NaOH (base)

Product: Ketone

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) of the oxidation reaction of 2° alcohols w/ CrO₃?

Starting Material: 2° alcohol

Reagents: CrO₃ (oxidizing agent), H₂SO₄ (acid), H₂O

Product: Ketone

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) of the oxidation reaction of 2° alcohols w/ Na₂Cr₂O₇?

Starting Material: 2° alcohol

Reagents: Na₂Cr₂O₇ (oxidizing agent), H₂SO₄ (acid), H₂O

Product: Ketone

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) of Friedel-Crafts Acylation?

Starting Material: Aromatic ring, Acid chloride

Reagents: AlCl₃ (Lewis acid catalyst)

Conditions: Heat

Product: Ketone

<p><span style="color: red;"><strong>Starting Material:</strong></span> Aromatic ring, Acid <strong>chloride</strong></p><p><span style="color: blue;"><strong>Reagents:</strong></span><span> AlCl<sub>3</sub> (Lewis acid catalyst)</span></p><p><span style="color: green;"><strong>Conditions:</strong></span><span> Heat</span></p><p><span style="color: purple;"><strong>Product:</strong></span><span> Ketone</span></p>

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) for hydration of alkynes w/ HgSO₄?

Starting Material: Alkyne (terminal or internal alkyne)

Reagents: H₂O, H₂SO₄ (acid), HgSO₄

Product:

If starting material is terminal alkyne: methyl ketone is produced
If starting material is non-symmetrical, internal alkyne: a mixture of regioisomeric ketones
are produced
If starting material is symmetrical, internal alkyne: a single ketone product is produced

<p><span style="color: red;"><strong>Starting Material:</strong></span> Alkyne (terminal or internal alkyne)</p><p><span style="color: blue;"><strong>Reagents:</strong></span> H<sub>2</sub>O, H<sub>2</sub>SO<sub>4</sub> (acid), HgSO<sub>4</sub></p><p><span style="color: purple;"><strong>Product:</strong></span> </p><ul><li><p>If starting material is <em>terminal alkyne</em>: <strong>methyl ketone</strong> is produced</p></li><li><p>If starting material is <em>non-symmetrical, internal alkyne</em>: a <strong>mixture of regioisomeric ketones</strong></p><p> are produced</p></li><li><p>If starting material is <em>symmetrical, internal alkyne</em>: a <strong>single ketone</strong> product is produced</p></li></ul><p></p>

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) for hydroboration-oxidation of alkynes w/ BH₃?

Starting Material: alkyne (terminal or internal)

Reagents:

BH₃, THF (solvent)
H₂O₂ (oxidizing agent), H₂O, NaOH (base)

Product:

If terminal alkyne: aldehyde is produced
If internal alkyne: ketone is produced

<p><span style="color: red;"><strong>Starting Material:</strong></span> alkyne (terminal or internal)</p><p><span style="color: blue;"><strong>Reagents: </strong></span></p><ol><li><p>BH<sub>3</sub>, THF (solvent)</p></li><li><p>H<sub>2</sub>O<sub>2</sub> (oxidizing agent), H<sub>2</sub>O, NaOH (base)</p></li></ol><p>Product:</p><ul><li><p>If <em>terminal alkyne</em>: <strong>aldehyde</strong> is produced</p></li><li><p>If <em>internal alkyne</em>: <strong>ketone</strong> is produced</p></li></ul><p></p>

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) for the reaction between an acid chloride and Gilman reagent?

Starting Material: acid chloride

Reagents: R₂’CuLi (Gilman reagent), Ether (solvent)

Product: Ketone

Note: Onlyonealkyl group is donated to the acid chloride

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) for the Grignard addition of nitriles?

Starting Material: nitrile compound

Reagents:

RMgX (Grignard reagent), ether (solvent)
H₂O (acid-workup step)

Product: Ketone

By-Product: NH₃

<p><span style="color: red;"><strong>Starting Material:</strong></span> nitrile compound</p><p><span style="color: blue;"><strong>Reagents:</strong></span> </p><ol><li><p>RMgX (Grignard reagent), ether (solvent)</p></li><li><p>H<sub>2</sub>O (acid-workup step)</p></li></ol><p><span style="color: purple;"><strong>Product: </strong></span><span>Ketone</span></p><p><span style="color: yellow;"><strong>By-Product:</strong></span><span> NH<sub>3</sub></span></p>

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What are the different reactions that can make both aldehydes and/or ketones?

Ozonolysis of alkenes
Hydroboration-oxidation of alkynes w/ BH₃

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) for the ozonolysis of alkenes?

Starting Material: alkene

Reagents:

O₃
Zn/H₃O⁺ (reducing agent)

Products:

Can be the following set of products:

2 aldehydes
1 ketone, 1 aldehyde
2 ketones
- Depends on how substituted the alkene functional group is!

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What are the different ways to make a nitrile compound?

S_N2 substitution w/ cyanide
Dehydration of 1° amides

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) for the S_N2 substitution w/ cyanide?

Starting Material: aldehyde or unhindered ketone

Reagents: HCN, base

Product: cyanohydrin (a type of nitrile)

Note: limited to steric hindrance due to S_N2 mechanism

<p><span style="color: red;"><strong>Starting Material:</strong></span> aldehyde or <em>unhindered</em> ketone</p><p><span style="color: blue;"><strong>Reagents:</strong></span> HCN, base</p><p><span style="color: purple;"><strong>Product:</strong></span> cyanohydrin (a type of nitrile)</p><ul><li><p>Note: limited to <em>steric hindrance</em> due to S<sub>N</sub>2 mechanism</p></li></ul><p></p>

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What are the starting materials, reagents, conditions (if application), products and by-products (if applicable) for the dehydration of 1° amides?

Starting Material: 1° amide

Reagents:

SOCl₂, benzene
Base

Conditions: 80°C

Product: nitrile compound

By-Products: SO₂

Note: not limited to steric hindrance (unlike S_N2 substitution of CN)

<p><span style="color: red;"><strong>Starting Material:</strong></span> 1° amide</p><p><span style="color: blue;"><strong>Reagents:</strong></span> </p><ol><li><p>SOCl<sub>2</sub>, benzene</p></li><li><p>Base</p></li></ol><p><span style="color: green;"><strong>Conditions:</strong></span> 80°C</p><p><span style="color: purple;"><strong>Product:</strong></span> nitrile compound</p><p><span style="color: yellow;"><strong>By-Products:</strong></span> SO<sub>2</sub></p><ul><li><p>Note: <em>not</em> limited to steric hindrance (unlike S<sub>N</sub>2 substitution of CN)</p></li></ul><p></p>

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