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Ochem DD > Chapter 18 > Flashcards

Chapter 18 Flashcards

1
Q
A
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2
Q

What is the mechanism for nucleophilic addition under basic conditions?

A
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3
Q

What is the mechanism for nucelophilic addition under acidic conditions?

A
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4
Q

Give the reagents necessary to transform each of the following starting materials
into 2-phenylethan-1-ol.

(Ph)CH=CH2

A
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5
Q

Give the reagents necessary to transform each of the following starting materials
into 2-phenylethan-1-ol.

A
  1. LiAlH4
  2. H3O+
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6
Q

Give the reagents necessary to transform each of the following starting materials
into 2-phenylethan-1-ol.

Bromobenzene

A
  1. Mg, Et2O
  2. Ethylene oxide (epoxide)
  3. H3O
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7
Q

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.

2-Heptanol

A

Note: You can make the necessary epoxide by dehydration of propanol followed by oxidation with m-CPBA.

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8
Q

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.

1-Butanethiol

A
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9
Q

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.

2-Hexanol

A
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10
Q

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.

** 2-Hexanone - CH3CO(CH2)3CH3**

A
  1. PBr3
  2. Mg, Et2O
  3. Acetaldehyde
  4. H3O+
  5. CrO3, aq. H2SO4
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11
Q

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.

2-Methyl-1,2-propanediol

A
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12
Q

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.

2,2-Dimethylpropanal - (CH3)3CCHO

A
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13
Q

Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.

Hexanoic acid - CH3(CH2)4CO2H

A
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14
Q

Dess Martin Reaction (Periodinane)

A
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15
Q

Give reagents that accomplish the following transformation.

A
  1. PBr3
  2. ((CH3)2CH)2CuLi Gilman reagent
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16
Q

Give reagents that accomplish the following transformation.

A
  1. H2, Lindlar’s Catalyst
  2. O3; Zn, H3O+
17
Q

Give reagents that accomplish the following transformation.

A
  1. BH3, THF
  2. H2O2, aq. NaOH
  3. NaH
  4. CH3CH2CH2Br
18
Q

Give reagents that accomplish the following transformation.

A
  1. NaOtBu, tBuOH
  2. mCPBA
  3. NaOMe, MeOH
  4. NaH; MeI
19
Q

What happens when you react TMSO with PCC?

A

Compound A is oxidized using PCC and then reacted with methyl magnesium bromide,
CH3MgBr, to form Compound B.

http://pages.towson.edu/jdiscord/www/332_answer_keys/Chapters_17_and_19/PracticeExam1AnsKey.pdf

20
Q

What are the reagents used to protect an alcohol before reacting Grignards?

How do you unprotect it after the reaction?

A

Protect with: 1. Me3SiCl, Et3N

De-protection: H3O+

21
Q

How do you reduce a ketone or aldehyde into an alkane?

(Clemmenson Reaction)

A

Zn(Hg)/
HCl, H2O

22
Q

What is the product?

A
23
Q

What is the mechanism for cis diol formation from and alkene?

A
24
Q

What is the reagent for cleaving an expoxide to yield trans diols?

A
25
Q

What reagents cleave an epoxide to yield cis diols?

A
26
Q

How do you reduce esters to alcohols?

A
27
Q

How do you add Br to the benzylic position a the end of CH3 in Ph-CH3?

A
28
Q
A
29
Q
A

Claisen rearrangement followed by Diels-Alder

Tautomerization of the Claisen product to a phenol does not take place because no H is available to dontate to the Oxygen.

30
Q
A

Ochem DD (9 decks)

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