ORGO 2 EXAM 3

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33 Terms

1
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NaBH4 reduction how many steps

1 step

2
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LiAlH4 reduction how many steps

2 steps

3
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<p>NaBH<sub>4 </sub>or LiAlH<sub>4 </sub>good reducing agent</p>

NaBH4 or LiAlH4 good reducing agent

Both NaBH4 and LiAlH4

4
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<p>NaBH<sub>4 </sub>or LiAlH<sub>4 </sub>good reducing agent</p>

NaBH4 or LiAlH4 good reducing agent

Both NaBH4 and LiAlH4

5
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<p>NaBH<sub>4 </sub>or LiAlH<sub>4 </sub>good reducing agent</p>

NaBH4 or LiAlH4 good reducing agent

Both NaBH4 and LiAlH4

6
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<p>NaBH<sub>4 </sub>or LiAlH<sub>4 </sub>good reducing agent</p>

NaBH4 or LiAlH4 good reducing agent

Only LiAlH4

7
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<p>NaBH<sub>4 </sub>or LiAlH<sub>4 </sub>good reducing agent</p>

NaBH4 or LiAlH4 good reducing agent

Only LiAlH4

8
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<p>NaBH<sub>4 </sub>or LiAlH<sub>4 </sub>good reducing agent</p>

NaBH4 or LiAlH4 good reducing agent

Only LiAlH4

9
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Grignard reagent + formaldehyde makes

Primary Alcohol

10
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Grignard reagent + aldehyde makes

Secondary alcohol

11
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Grignard reagent + ketone makes

Tertiary alcohol

12
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Grignard reagent + acid chloride makes

Tertiary alcohol, Cl is LG

(This is made after an acid workup)

13
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Grignard reagent + epoxide makes

Primary alcohol with 2 extra carbons

MgBr strong nucleophile, attacks less hinder Carbon

14
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Grignard reagent + CO2 makes

Carboxylic acid after acid workup

15
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Limitations of Grignard reagent

Protic reagents such as water, alcohols, amines because grignard is very strong base

16
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Acid catalyzed ring opening of epoxides steps with reagents, FINAL PRODUCT

  1. Protonation, oxygen attacks H+

  2. Ring opening, H2O attacks more substituted carbon

  3. Deprotonation, water attack H+ on other water

FINAL PRODUCT: Anti-diol

17
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Base catalyzed ring opening of epoxides, steps, final product

  1. Nucleophile (-OH) attack on less hindered Carbon

  2. Protonation, (by water)

Final Product: Anti-diol

18
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What constitutes reduction

  • Loss of O or O2

  • Loss of X2

  • Gain of H

19
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What constitutes oxidation

  • Gaining of O

  • Gaining X2

  • Loss of H

20
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Primary alcohol → aldehyde reagents

PCC, CH2Cl2

21
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Primary alcohol → Carboxylic acid reagents

Na2Cr2O7 , H2SO4

22
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Secondary alcohol → Ketone reagents

PCC / CH2Cl2

OR

Na2Cr2O7 / H2SO4

23
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How to make symmetrical ether

Bimolecular dehydration of alcohol

24
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Bimolecular vs unimolecular dehydration of alcohol

Unimolecular - higher temp, makes alkene

Bimolecular- 2 reactants, lower temp, makes symmetrical ether + H2O

25
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Bimolecular dehydration of alcohol reagents

H2SO4 , Heat (lower)

26
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To make asymmetrical ether

Williamson ether synthesis

27
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Williamson ether synthesis reagents

  1. NaH

  2. Alkyl halide (SN2)

28
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Primary alcohol → alkyl halide reagents for Cl, Br, and I

Chloride: SOCl2

Bromide: PBr3

Iodide: P/I2

29
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Secondary alcohol → alkyl halide reagents for Cl, Br, and I

Chloride: SOCl2

Bromide: PBr3

Iodide: P/I2

30
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Tertiary alcohol → alkyl halide reagents for Cl, Br, and I

Chloride: HCl

Bromide: HBr

Iodide:HI

31
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Converting OH to good LG using tosylate or tosyl chloride TsCl steps reagents

  1. TsCl, pyridine

  2. NaX

32
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Tosylate method scheme

ROH → R-OTs → R-X

33
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-OTs

Very good LG