Final CHEM8B Reactions

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

1/20

encourage image

There's no tags or description

Looks like no tags are added yet.

Last updated 7:57 AM on 7/29/26
Name
Mastery
Learn
Test
Matching
Spaced
Call with Kai
Chat

No analytics yet

Send a link to your students to track their progress

21 Terms

1
New cards

Reaction: Alcohol Dehydration

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Alcohol

H₂SO₄, heat

Water leaves and H is removed

Forms the more stable alkene

Alkene

Elimination reaction (E1/E2 depending on substrate)

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alcohol</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>H₂SO₄, heat</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Water leaves and H is removed</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Forms the more stable alkene</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alkene</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Elimination reaction (E1/E2 depending on substrate)</strong></span></p></td></tr></tbody></table><p></p>
2
New cards

Reaction: Williamson Ether Synthesis

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Alkoxide + Methyl/1° Alkyl Halide

R–X

Alkoxide attacks carbon by SN2

Alkoxide is a strong nucleophile; methyl/1° carbons allow SN2

Ether

Best way to make ethers

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alkoxide + Methyl/1° Alkyl Halide</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>R–X</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alkoxide attacks carbon by SN2</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alkoxide is a strong nucleophile; methyl/1° carbons allow SN2</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Ether</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Best way to make ethers</strong></span></p></td></tr></tbody></table><p></p>
3
New cards

Reaction: Alkoxymercuration

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Alkene

Hg(OAc)₂, ROH; NaBH₄

Alcohol adds across the double bond

Avoids carbocation rearrangements

Ether

Markovnikov addition without rearrangement

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alkene</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Hg(OAc)₂, ROH; NaBH₄</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alcohol adds across the double bond</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Avoids carbocation rearrangements</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Ether</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Markovnikov addition without rearrangement</strong></span></p></td></tr></tbody></table><p></p>
4
New cards

Reaction:

Ether Cleavage

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Ether

HI or HBr

Protonate O, then C–O bond breaks

Protonation makes oxygen a good leaving group

Alcohol + Alkyl Halide

Breaks ethers apart

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Ether</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>HI or HBr</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Protonate O, then C–O bond breaks</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Protonation makes oxygen a good leaving group</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alcohol + Alkyl Halide</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Breaks ethers apart</strong></span></p></td></tr></tbody></table><p></p>
5
New cards

Reaction: Epoxidation

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Alkene

mCPBA

Oxygen adds across double bond

Weak O–O bond transfers oxygen

Epoxide

Alkene → Epoxide

6
New cards

Reaction: Halohydrin Cyclization

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Halohydrin

NaOH

Alkoxide attacks neighboring carbon

Intramolecular SN2 closes the ring

Epoxide

Forms an epoxide ring

7
New cards

Reaction: Acidic Epoxide Opening

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Epoxide

H₃O⁺

Ring opens; nucleophile attacks more substituted carbon

Protonated epoxide has more positive character on the more substituted carbon

Alcohol

Acid → More substituted attack

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Epoxide</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>H₃O⁺</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Ring opens; nucleophile attacks more substituted carbon</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Protonated epoxide has more positive character on the more substituted carbon</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alcohol</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Acid → More substituted attack</strong></span></p></td></tr></tbody></table><p></p>
8
New cards

Reaction: Basic Epoxide Opening

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Epoxide

OH⁻, RO⁻, CN⁻

Ring opens by SN2

Strong nucleophile attacks least hindered carbon

Alcohol

Base → Less substituted attack

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Epoxide</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>OH⁻, RO⁻, CN⁻</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Ring opens by SN2</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Strong nucleophile attacks least hindered carbon</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alcohol</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Base → Less substituted attack</strong></span></p></td></tr></tbody></table><p></p>
9
New cards

Reaction: NaBH₄ Reduction

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Aldehyde or Ketone

NaBH₄

Hydride attacks carbonyl carbon

Carbonyl carbon is electrophilic

Alcohol

Adds H⁻

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Aldehyde or Ketone</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>NaBH₄</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Hydride attacks carbonyl carbon</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Carbonyl carbon is electrophilic</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alcohol</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Adds H⁻</strong></span></p></td></tr></tbody></table><p></p>
10
New cards

Reaction: LiAlH₄ Reduction

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Aldehyde, Ketone (also esters, acids, etc.)

LiAlH₄ then H₃O⁺

Hydride attacks carbonyl carbon

Strong reducing agent

Alcohol

Stronger than NaBH₄

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Aldehyde, Ketone (also esters, acids, etc.)</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>LiAlH₄ then H₃O⁺</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Hydride attacks carbonyl carbon</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Strong reducing agent</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alcohol</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Stronger than NaBH₄</strong></span></p></td></tr></tbody></table><p></p>
11
New cards

Reaction: DIBAL-H Reduction

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Ester or Nitrile

DIBAL-H

Partial reduction

Stops before full reduction under controlled conditions

Aldehyde

Partial reduction

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Ester or Nitrile</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>DIBAL-H</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Partial reduction</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Stops before full reduction under controlled conditions</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Aldehyde</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Partial reduction</strong></span></p></td></tr></tbody></table><p></p>
12
New cards

Reaction: Grignard Reaction

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Aldehyde or Ketone

RMgBr then H₃O⁺

Carbon nucleophile attacks carbonyl

Carbon attached to Mg behaves like C⁻

Larger Alcohol

Forms a new C–C bond

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Aldehyde or Ketone</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>RMgBr then H₃O⁺</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Carbon nucleophile attacks carbonyl</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Carbon attached to Mg behaves like C⁻</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Larger Alcohol</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Forms a new C–C bond</strong></span></p></td></tr></tbody></table><p></p>
13
New cards

Reaction: Oxime Formation

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Aldehyde or Ketone

NH₂OH or 2,4 DNP

Nitrogen attacks carbonyl; water leaves

Stable C=N bond forms

Oxime

NH₂OH → Oxime

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Aldehyde or Ketone</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>NH₂OH or 2,4 DNP</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Nitrogen attacks carbonyl; water leaves</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Stable C=N bond forms</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Oxime</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>NH₂OH → Oxime</strong></span></p></td></tr></tbody></table><p></p>
14
New cards

Reaction: Imine Formation

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Aldehyde or Ketone

RNH₂, H⁺

Primary amine attacks carbonyl; water leaves

Forms stable C=N bond

Imine

1° amine → Imine

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Aldehyde or Ketone</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>RNH₂, H⁺</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Primary amine attacks carbonyl; water leaves</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Forms stable C=N bond</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Imine</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>1° amine → Imine</strong></span></p></td></tr></tbody></table><p></p>
15
New cards

Reaction: Acetal Formation

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Aldehyde

ROH, H⁺

Two OR groups replace carbonyl oxygen

Protects aldehyde from further reactions

Acetal

Protecting group

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Aldehyde</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>ROH, H⁺</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Two OR groups replace carbonyl oxygen</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Protects aldehyde from further reactions</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Acetal</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Protecting group</strong></span></p></td></tr></tbody></table><p></p>
16
New cards

Reaction: Ketal Formation

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Ketone

ROH, H⁺

Two OR groups replace carbonyl oxygen

Protects ketone

Ketal

Protecting group

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Ketone</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>ROH, H⁺</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Two OR groups replace carbonyl oxygen</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Protects ketone</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Ketal</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Protecting group</strong></span></p></td></tr></tbody></table><p></p>
17
New cards

Reaction: Acetal/Ketal Hydrolysis

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Acetal or Ketal

H₃O⁺

Removes protecting group

Acid reverses acetal formation

Aldehyde or Ketone

Deprotection

18
New cards

Reaction: Wittig Reaction

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Aldehyde or Ketone

Ph₃P=CHR

Ylide replaces oxygen with carbon

Strong P=O bond drives reaction

Alkene

Carbonyl → Alkene

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Aldehyde or Ketone</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Ph₃P=CHR</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Ylide replaces oxygen with carbon</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Strong P=O bond drives reaction</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alkene</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Carbonyl → Alkene</strong></span></p></td></tr></tbody></table><p></p>
19
New cards

Reaction: Cannizzaro Reaction

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Aldehyde (no α-H)

OH⁻

One aldehyde oxidized, another reduced

Hydride transfer between aldehydes

Alcohol + Carboxylate

Requires NO α-hydrogens

<table style="min-width: 150px;"><colgroup><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"><col style="min-width: 25px;"></colgroup><tbody><tr><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Aldehyde (no α-H)</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>OH⁻</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>One aldehyde oxidized, another reduced</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Hydride transfer between aldehydes</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Alcohol + Carboxylate</strong></span></p></td><td colspan="1" rowspan="1" style="vertical-align: top; padding: 5pt; overflow: hidden; overflow-wrap: break-word;"><p><span style="background-color: transparent;"><strong>Requires NO α-hydrogens</strong></span></p></td></tr></tbody></table><p></p>
20
New cards

Reaction: Radical Halogenation

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Alkane

Cl₂ or Br₂, hν

H replaced by halogen

UV light forms radicals

Alkyl Halide

Initiation → Propagation → Termination

21
New cards

Reaction: Radical HBr Addition

Starting Material

Reagent(s)

What Happens?

Why Does It Happen?

Product

Key Idea ⭐

Alkene

HBr, ROOR

Br adds across double bond

Radical mechanism favors more stable radical intermediate

Alkyl Bromide

Anti-Markovnikov addition