Alcohol UNIT 9 reagants and products

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Last updated 12:48 AM on 7/27/26
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1
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<p>2<sup>o</sup>/3<sup>o </sup>alcohol + HX (1. What mechanism 2. what product)</p>

2o/3o alcohol + HX (1. What mechanism 2. what product)

  1. SN1 (because forms a stable carbocation)

  2. quite literally youre substituting the alcohol for a Br, first got to make OH weak through the acid

  3. which means it would have both configurations (wedge and dash)

<ol><li><p><mark data-color="yellow" style="background-color: yellow; color: inherit;">SN1</mark> (because forms a stable carbocation)</p></li><li><p>quite literally youre substituting the alcohol for a Br, first got to make OH weak through the acid</p></li><li><p>which means it would have both configurations (wedge and dash)</p></li></ol><p></p>
2
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<p>1<sup>o </sup>alcohol + HX (1. What mechanism 2. what product)</p>

1o alcohol + HX (1. What mechanism 2. what product)

  1. SN2 (primary no stable carbocation)

  2. Adopts the OPPOSITE configuration as the alcohol (with on the plane being an exception)

<ol><li><p><mark data-color="yellow" style="background-color: yellow; color: inherit;">SN2 </mark>(primary no stable carbocation)</p></li><li><p>Adopts the <mark data-color="yellow" style="background-color: yellow; color: inherit;">OPPOSITE configuration</mark> as the alcohol (with on the plane being an exception) </p></li></ol><p></p>
3
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<p>2<sup>o</sup>/3<sup>o </sup>alcohol + <mark data-color="yellow" style="background-color: yellow; color: inherit;">H<sub>2</sub>SO<sub>4</sub></mark> / TsOH (1. What mechanism 2. what product)</p>

2o/3o alcohol + H2SO4 / TsOH (1. What mechanism 2. what product)

  1. E1 (again carbocation stability; this also means there could be hydride and methyl shifts)

  2. forms an ALKENE no substitution business

  3. most substituted alkene

<ol><li><p><mark data-color="yellow" style="background-color: yellow; color: inherit;">E1</mark> (again carbocation stability; <mark data-color="yellow" style="background-color: yellow; color: inherit;">this also means there could be hydride and methyl shifts</mark>)</p></li><li><p>forms an <mark data-color="yellow" style="background-color: yellow; color: inherit;">ALKENE</mark> no substitution business</p></li><li><p>most substituted alkene</p></li></ol><p></p>
4
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<p>1<sup>o </sup>alcohol + H<sub>2</sub>SO<sub>4 </sub>/ TsOH (1. What mechanism 2. what product)</p>

1o alcohol + H2SO4 / TsOH (1. What mechanism 2. what product)

  1. E2 (make sure the hydrogen and forged leaving group are anti but remember with free rotation a hydrogen can become anti with the leaving group)

  2. ALKENE

<ol><li><p><mark data-color="yellow" style="background-color: yellow; color: inherit;">E2 </mark>(make sure the hydrogen and forged leaving group are anti but remember with free rotation a hydrogen can become anti with the leaving group)</p></li><li><p><mark data-color="yellow" style="background-color: yellow; color: inherit;">ALKENE </mark></p></li></ol><p></p>
5
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<p>ANY alcohol + POCl<sub>3 </sub>and pyridine (1. what mechanism 2. what product)</p>

ANY alcohol + POCl3 and pyridine (1. what mechanism 2. what product)

  1. E2

  2. pyridine is NOT polar protic and basic as fuck meaning no substitutions and carbocations (E1)

  3. ANOTHER F*KING ALKENE

<ol><li><p><mark data-color="yellow" style="background-color: yellow; color: inherit;">E2</mark></p></li><li><p>pyridine is NOT polar protic and basic as fuck meaning no substitutions and carbocations (E1)</p></li><li><p>ANOTHER F*KING <mark data-color="yellow" style="background-color: yellow; color: inherit;">ALKENE</mark></p></li></ol><p></p>
6
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<p>alcohol + SOCl<sub>2 </sub>and pyridine<sub> </sub>(1. what type of alcohol 2. mechanism 3. what product)</p>

alcohol + SOCl2 and pyridine (1. what type of alcohol 2. mechanism 3. what product)

  1. 1o/2o because its a

  2. SN2 mechanism; can’t happen on a tertiary

  3. Cl- (from the SOCl2) acts as a good nucleophile + OSOCl acts as a good leaving group

  4. the pyridine is acting as a base yes, but its for the hydogen thats’s on the oxygen after the SOCl2 attaches to the alcohol and loses the chlorine

  5. Cl substituted for OH on the OPPOSITE configuration as the alcohol

<ol><li><p>1<sup>o</sup>/2<sup>o </sup>because its a</p></li><li><p>SN2 mechanism; can’t happen on a tertiary</p></li><li><p>Cl- (from the SOCl2) acts as a good nucleophile + OSOCl acts as a good leaving group</p></li><li><p>the pyridine is acting as a base yes, but its for the hydogen thats’s on the oxygen after the SOCl2 attaches to the alcohol and loses the chlorine</p></li><li><p>Cl substituted for OH on the OPPOSITE configuration as the alcohol</p></li></ol><p></p>
7
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<p>alcohol + PBr<sub>3 </sub>(1. what type of alcohol 2. mechanism 3. what product)</p>

alcohol + PBr3 (1. what type of alcohol 2. mechanism 3. what product)

  1. ALSO 1o/2o because its ALSO a

  2. SN2 mechanism; can’t happen on a tertiary

  3. Br- just kicks out the OHPBr2 (nothing to remove the hydrogen)

  4. because its SN2 the Br has the OPPOSITE configuration as OH

<ol><li><p>ALSO 1<sup>o</sup>/2<sup>o </sup>because its ALSO a</p></li><li><p>SN2 mechanism; can’t happen on a tertiary</p></li><li><p>Br- just kicks out the OHPBr2 (nothing to remove the hydrogen)</p></li><li><p>because its SN2 the Br has the OPPOSITE configuration as OH</p></li></ol><p></p>
8
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HOW DOES TsCl look like?

knowt flashcard image
9
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<p>alcohol + TsCl</p>

alcohol + TsCl

WE’RE NOT DOING ANY SN1/SN2/E1/E2 here

  1. first the TsCl attaches to the OH through the Pi bond

  2. then it kicks out the Cl, regains the pi bond

  3. loses the H on the H—O—Ts complex

  4. hence you’re left with OTs

  5. RETENSION OF CONFIGURATION

<p>WE’RE NOT DOING ANY SN1/SN2/E1/E2 here</p><ol><li><p>first the TsCl attaches to the OH through the Pi bond</p></li><li><p>then it kicks out the Cl, regains the pi bond</p></li><li><p>loses the H on the H—O—Ts complex </p></li><li><p>hence you’re left with OTs </p></li><li><p>RETENSION OF CONFIGURATION</p></li></ol><p></p>
10
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You have an alcohol on a wedge and that turns into CN with a dash. What regeant are you using for this switch in configuration?

TsCl Because it retains the same configuration as the OH and chages configuration when the NaCN attacks

11
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You have a secondary alcohol on a wedge and that turn into a CN with a wedge also. What reagant are you using?

either SOCl3 or PBr, because either forms a Cl/ Br on a dash, then gets changed to a wedge when the NaCN attacks

12
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