Organic Chemistry Reactions

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Last updated 1:20 AM on 4/15/26
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81 Terms

1
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<p>H-X</p>

H-X

X adds Markovnikov

<p>X adds Markovnikov</p>
2
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<p>H-Br and ROOR</p>

H-Br and ROOR

X adds anti-Markovnikov

<p>X adds anti-Markovnikov</p>
3
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<p>H+ and H2O</p>

H+ and H2O

OH adds Markovnikov

<p>OH adds Markovnikov</p>
4
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<p>H3O+</p>

H3O+

OH adds Markovnikov

<p>OH adds Markovnikov</p>
5
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<p>H2SO4 (dilute)</p>

H2SO4 (dilute)

OH adds Markovnikov

<p>OH adds Markovnikov</p>
6
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<ol><li><p>Hg(OAc)2, H2O</p></li><li><p>NaBH4</p></li></ol><p></p>

  1. Hg(OAc)2, H2O

  2. NaBH4

OH adds Markovnikov, cannot rearrange

<p>OH adds Markovnikov, cannot rearrange</p>
7
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<ol><li><p>BH3</p></li><li><p>H2O2, NaOH</p></li></ol><p></p>

  1. BH3

  2. H2O2, NaOH

OH adds Anti-Markovnikov, groups add syn

<p>OH adds Anti-Markovnikov, groups add syn</p>
8
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<p>H2, Pt</p>

H2, Pt

H’s add syn

<p>H’s add syn</p>
9
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<p>X2</p>

X2

X’s add anti

<p>X’s add anti</p>
10
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<p>X2, H2O</p>

X2, H2O

OH adds Markovnikov, add anti

<p>OH adds Markovnikov, add anti</p>
11
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<ol><li><p>RCO3H</p></li><li><p>H3O+</p></li></ol><p></p>

  1. RCO3H

  2. H3O+

OH’s add anti

<p>OH’s add anti</p>
12
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<ol><li><p>OsO4</p></li><li><p>NaHSO3, H2O</p></li></ol><p></p>

  1. OsO4

  2. NaHSO3, H2O

OH’s add syn

<p>OH’s add syn</p>
13
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<ol><li><p>MCPBA</p></li><li><p>H3O+</p></li></ol><p></p>

  1. MCPBA

  2. H3O+

OH’s add anti

<p>OH’s add anti</p>
14
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<ol><li><p>O3</p></li><li><p>DMS</p></li></ol><p></p>

  1. O3

  2. DMS

cleavage

<p>cleavage</p>
15
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<p>NaNH2</p>

NaNH2

alkyne

<p>alkyne</p>
16
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<p>NaNH2</p>

NaNH2

alkyne

<p>alkyne</p>
17
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<p>HX</p>

HX

X adds Markovnikov

<p>X adds Markovnikov</p>
18
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<p>2HX</p>

2HX

2X adds Markovnikov

<p>2X adds Markovnikov</p>
19
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<p>2X2</p>

2X2

add 2 to each side of pi bonds

<p>add 2 to each side of pi bonds</p>
20
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<p>X2</p>

X2

Xs add anti

<p>Xs add anti</p>
21
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<p>HgSO4, H2SO4, H2O</p>

HgSO4, H2SO4, H2O

OH adds Markovnikov to make enol then tautomerization to ketone

<p>OH adds Markovnikov to make enol then tautomerization to ketone</p>
22
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<ol><li><p>R2BH</p></li><li><p>H2O2, NaOH</p></li></ol><p></p>

  1. R2BH

  2. H2O2, NaOH

OH adds anti Markovnikov to make enol then tautomerization to aldehyde

<p>OH adds anti Markovnikov to make enol then tautomerization to aldehyde</p>
23
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<p>H2, Pt</p>

H2, Pt

cannot stop at alkene, goes all the way to alkane

<p>cannot stop at alkene, goes all the way to alkane</p>
24
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<p>H2, Lindlar</p>

H2, Lindlar

H’s add syn

<p>H’s add syn</p>
25
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<p>Na, NH3</p>

Na, NH3

H’s add anti

<p>H’s add anti</p>
26
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<p>H2, Lindlar</p>

H2, Lindlar

only cis product is made

<p>only cis product is made</p>
27
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<p>Na, NH3</p>

Na, NH3

only trans product is made

<p>only trans product is made</p>
28
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<ol><li><p>O3</p></li><li><p>H2O</p></li></ol><p></p>

  1. O3

  2. H2O

ozonolysis

<p>ozonolysis</p>
29
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<ol><li><p>O3</p></li><li><p>H2O</p></li></ol><p></p>

  1. O3

  2. H2O

ozonolysis

<p>ozonolysis</p>
30
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<ol><li><p>NaNH2</p></li><li><p>low substituted alpha carbon</p></li></ol><p></p>

  1. NaNH2

  2. low substituted alpha carbon

coupling reaction

<p>coupling reaction</p>
31
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<p>Br2 and light (hv)</p>

Br2 and light (hv)

Br adds most substituted

<p>Br adds most substituted</p>
32
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<p>NBS and light (hv)</p>

NBS and light (hv)

Br adds more substituted allylic

<p>Br adds more substituted allylic</p>
33
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<p>H2O</p>

H2O

only works on tertiary alpha C

<p>only works on tertiary alpha C</p>
34
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<p>NaOH</p>

NaOH

only works on primary alpha C

<p>only works on primary alpha C</p>
35
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<p>NaBH4 and ROH</p>

NaBH4 and ROH

mild reduction

<p>mild reduction</p>
36
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<ol><li><p>LAH </p></li><li><p>H2O</p></li></ol><p></p>

  1. LAH

  2. H2O

strong reduction

<p>strong reduction</p>
37
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<ol><li><p>RMgBr</p></li><li><p>H2O</p></li></ol><p></p>

  1. RMgBr

  2. H2O

reduction and coupling

<p>reduction and coupling</p>
38
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<ol><li><p>RMgBr</p></li><li><p>H2O</p></li></ol><p></p>

  1. RMgBr

  2. H2O

reduction and coupling

<p>reduction and coupling</p>
39
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<p>HX</p>

HX

only works on primary or tertiary alpha carbons

<p>only works on primary or tertiary alpha carbons</p>
40
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<p>SOCl2</p>

SOCl2

Cl adds 180 opposite

<p>Cl adds 180 opposite</p>
41
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<p>PBr3</p>

PBr3

Br adds 180 opposite

<p>Br adds 180 opposite</p>
42
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<p>PCC</p>

PCC

mild oxidation

<p>mild oxidation</p>
43
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<p>CrO3</p>

CrO3

strong oxidation

<p>strong oxidation</p>
44
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<p>H2SO4 (cat) + heat</p>

H2SO4 (cat) + heat

makes a symmetrical ether

<p>makes a symmetrical ether</p>
45
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<ol><li><p>NaH</p></li><li><p>R’X (primary substituted)</p></li></ol><p></p>

  1. NaH

  2. R’X (primary substituted)

can create uneven ether

<p>can create uneven ether</p>
46
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<ol><li><p>Hg(OAc)2, ROH</p></li><li><p>NaBH4</p></li></ol><p></p>

  1. Hg(OAc)2, ROH

  2. NaBH4

OR adds more substituted

<p>OR adds more substituted</p>
47
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<p>HX(excess) + heat</p>

HX(excess) + heat

(+H2O) breaks ethers

<p>(+H2O) breaks ethers</p>
48
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<p>TmsCl</p>

TmsCl

protected alcohol (silyl ether)

<p>protected alcohol (silyl ether)</p>
49
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<p>H3O+</p>

H3O+

deprotected alcohol

<p>deprotected alcohol</p>
50
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<p>MCPBA</p>

MCPBA

epoxide preparation

<p>epoxide preparation</p>
51
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<ol><li><p>X2, H2O</p></li><li><p>NaOH</p></li></ol><p></p>

  1. X2, H2O

  2. NaOH

epoxide preparation

<p>epoxide preparation</p>
52
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<ol><li><p>NaOR</p></li><li><p>H2O</p></li></ol><p></p>

  1. NaOR

  2. H2O

basic condition, OR attaches less substituted

<p>basic condition, OR attaches less substituted</p>
53
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<ol><li><p>NaCN</p></li><li><p>H2O</p></li></ol><p></p>

  1. NaCN

  2. H2O

basic condition, CN adds less substituted

<p>basic condition, CN adds less substituted</p>
54
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<ol><li><p>NaSH</p></li><li><p>H2O</p></li></ol><p></p>

  1. NaSH

  2. H2O

basic condition, SH adds less substituted

<p>basic condition, SH adds less substituted</p>
55
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<ol><li><p>RMgBr</p></li><li><p>H2O</p></li></ol><p></p>

  1. RMgBr

  2. H2O

basic condition, R group adds less substituted

<p>basic condition, R group adds less substituted</p>
56
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<ol><li><p>LAH</p></li><li><p>H2O</p></li></ol><p></p>

  1. LAH

  2. H2O

basic condition, H adds less substituted

<p>basic condition, H adds less substituted</p>
57
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<p>HX</p>

HX

acidic condition, x adds 3>1>2

<p>acidic condition, x adds 3&gt;1&gt;2</p>
58
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<p>H3O+</p>

H3O+

acidic condition, OH adds 3>1>2

<p>acidic condition, OH adds 3&gt;1&gt;2</p>
59
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<p>H+ and ROH</p>

H+ and ROH

acidic condition, OR adds 3>1>2

<p>acidic condition, OR adds 3&gt;1&gt;2</p>
60
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<p>NaSH</p>

NaSH

backside attack, alkyl halide to thiol

<p>backside attack, alkyl halide to thiol</p>
61
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<ol><li><p>NaH</p></li><li><p>RX</p></li></ol><p></p>

  1. NaH

  2. RX

thiol to sulfide

<p>thiol to sulfide</p>
62
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<p>t-bOK</p>

t-bOK

conjugated diene preparation

<p>conjugated diene preparation</p>
63
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<p>HX</p>

HX

1,2 and 1,4 addition

<p>1,2 and 1,4 addition</p>
64
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<p>X2</p>

X2

1,2 and 1,4 addition

<p>1,2 and 1,4 addition</p>
65
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<p>heat</p>

heat

diels alder reaction

<p>diels alder reaction</p>
66
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<p>hv</p>

hv

2+2 addition

<p>2+2 addition</p>
67
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<p>hv</p>

hv

4+4 addition

<p>4+4 addition</p>
68
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<p>KMnO4</p>

KMnO4

strong oxidation

<p>strong oxidation</p>
69
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<p>NaCl</p>

NaCl

Cl replacement

<p>Cl replacement</p>
70
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<p>HCl</p>

HCl

Cl replacement

<p>Cl replacement</p>
71
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<p>NBS, hv</p>

NBS, hv

Br adds at benzylic position

<p>Br adds at benzylic position</p>
72
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<p>Br2, FeBr3</p>

Br2, FeBr3

+HBr

<p>+HBr</p>
73
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<p>H2SO4 (conc)</p>

H2SO4 (conc)

+H2O

<p>+H2O</p>
74
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<p>R-Cl, AlCl3</p>

R-Cl, AlCl3

+HCl

<p>+HCl</p>
75
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<p>Cl2, AlCl3</p>

Cl2, AlCl3

+HCl

<p>+HCl</p>
76
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<p>HNO3, H2SO4</p>

HNO3, H2SO4

+H2O

<p>+H2O</p>
77
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<p>Cl-C=O plus R group, AlCl3</p>

Cl-C=O plus R group, AlCl3

+HCl

<p>+HCl</p>
78
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<p>Zn, HCl</p>

Zn, HCl

.

<p>.</p>
79
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<p>H2SO4 (dilute)</p>

H2SO4 (dilute)

.

<p>.</p>
80
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<p>Zn/Hg, HCl</p>

Zn/Hg, HCl

.

<p>.</p>
81
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<p>KMnO4, H3O+</p>

KMnO4, H3O+

.

<p>.</p>