Organic Chemistry Synthesis Reactions and Reagents

0.0(0)
Studied by 0 people
call kaiCall Kai
learnLearn
examPractice Test
spaced repetitionSpaced Repetition
heart puzzleMatch
flashcardsFlashcards
GameKnowt Play
Card Sorting

1/17

encourage image

There's no tags or description

Looks like no tags are added yet.

Last updated 1:36 AM on 10/7/26
Name
Mastery
Learn
Test
Matching
Spaced
Call with Kai
Chat

No analytics yet

Send a link to your students to track their progress

18 Terms

1
New cards

Williamson Ether Synthesis

1) NaH

2) RX

Synthesizes an ether from an alcohol.

<p>1) NaH</p><p>2) RX</p><p>Synthesizes an <strong>ether </strong>from an <strong>alcohol.</strong></p>
2
New cards

Alkoxymercuration-demercuration

1) Mg(OAc)2, ROH

2) NaBH4

Synthesizes an ether from an alkene.

<p>1) Mg(OAc)<sub>2</sub>, ROH</p><p>2) NaBH4</p><p>Synthesizes an <strong>ether</strong> from an <strong>alkene.</strong> </p>
3
New cards

Acid-promoted Cleavage of Ethers

1) Excess HX, heat

Produces an alcohol and alkyl halide from an ether.

Carbons must be sp3 hybridized.

<p>1) Excess HX, heat</p><p>Produces an <strong>alcohol</strong> and <strong>alkyl halide</strong> from an<strong> ether.</strong></p><p>Carbons must be sp<sup>3</sup> hybridized.</p>
4
New cards

Epoxidation of Alkenes

1) RCO3 or MCPBA

Synthesizes an epoxide from an alkene.

  • Stereospecific. Will form a cis epoxide from a cis alkene and a trans epoxide from a trans alkene.


<p>1) RCO<sub>3</sub> or MCPBA</p><p>Synthesizes an <strong>epoxide</strong> from an alkene.</p><ul><li><p><strong>Stereospecific.</strong> Will form a cis epoxide from a cis alkene and a trans epoxide from a trans alkene.</p></li></ul><p></p>
5
New cards

Epoxidation of Halohydrins

1) NaOH

Produces an epoxide from a halohydrin.

<p>1) NaOH</p><p>Produces an <strong>epoxide </strong>from a <strong>halohydrin.</strong></p>
6
New cards

Ring-Opening Reactions of Epoxides

1) A strong nucleophile (NaOR, NaCN, NaSR, RMgBr, LiAlH4)

2) H3O+

Opens the ring of an epoxide, forming an alcohol and attaching the nucleophilic molecule to the less-substituted carbon.

  • Under acidic conditions (H2SO4), if a tertiary carbon is present, the nucleophilic molecule will attach to that carbon instead.


<p>1) A strong nucleophile (NaOR, NaCN, NaSR, RMgBr, LiAlH4)</p><p>2) H3O<sup>+</sup></p><p>Opens the ring of an <strong>epoxide,</strong> forming an <strong>alcohol</strong> and attaching the <strong>nucleophilic</strong> <strong>molecule</strong> to the <strong>less-substituted carbon.</strong></p><ul><li><p>Under <strong>acidic conditions (</strong>H<sub>2</sub>SO<sub>4</sub>), if a <strong>tertiary carbon</strong> is present, the nucleophilic molecule will attach to that carbon instead.</p></li></ul><p></p>
7
New cards

Oxidation of Thiols

1) Br2, NaOH, H2O

Forms a disulfide from two thiols.

<p>1) Br<sub>2</sub>, NaOH, H<sub>2</sub>O</p><p>Forms a <strong>disulfide</strong> from two <strong>thiols.</strong></p>
8
New cards

Reduction of Disulfides

1) HCl, Zn

Forms two thiols from a disulfide. (The inverse of oxidation of thiols)

<p>1) HCl, Zn</p><p>Forms <strong>two thiols</strong> from a <strong>disulfide. </strong>(The inverse of oxidation of thiols)</p>
9
New cards

Sulfoxidation

1) NaIO4

Forms a sulfoxide from a sulfide.

<p>1) NaIO<sub>4</sub></p><p>Forms a <strong>sulfoxide</strong> from a <strong>sulfide.</strong></p>
10
New cards

Sulfonation

1) 2H2O2

Forms a sulfone from a sulfide.

<p>1) 2H<sub>2</sub>O<sub>2</sub></p><p>Forms a <strong>sulfone </strong>from a <strong>sulfide.</strong></p>
11
New cards

Halogenation (EAS)

1) FeBr3 or AlBr3 or AlCl3

An aromatic proton is replaced by a halogen

12
New cards

Sulfonation (EAS)

1) Concentrated fuming H2SO4

An aromatic proton is replaced by SO3

13
New cards

Nitration (EAS)

1) HNO3 with H2SO4

An aromatic proton replaced by NO2

14
New cards

Friedel-Crafts Alkylation

1) Alkyl Halide with AlCl3

An aromatic proton is replaced with an alkyl group.

15
New cards

Friedel-Crafts Acylation

1) Acyl Halide with AlCl3

An aromatic proton is replaced with an acyl group.

16
New cards

Clemmensen Reduction

Zn(Hg) with HCl, heat

A carbonyl oxygen is replaced with two hydrogen atoms, reducing a ketone or aldehyde and forming the corresponding alkane.

17
New cards

Nucleophilic Aromatic Substitution

1) Strong NP

2) H3O+

Replaces a leaving group with a strong nucleophile. Requires an EWG and a good leaving group positioned ortho or para to the EWG.

18
New cards

Elimination-Addition via Benzyne

1) Strong NP, 350โ„ƒ

2) H3O+