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Ochem 2 > Quiz 5 > Flashcards

Quiz 5 Flashcards

1
Q

What is the difference between enamine and imine formation?

A

Enamine formation is different in the last proton transfer step that creates the C=C bond of an enamine

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2
Q

LiAlH and NaBH4 are —- —

A

reducing agents

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3
Q

True or false?

LAH will not reduce carboxylic acids or esters

A

false, it is strong enough to react with them but NaBH4 is not

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4
Q

The grignard reagent is a — —-

A

reducing agent

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5
Q

What is necessary to react a carboxylic acid with a grignard reagent?

A

a blocking group on the acidic proton

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6
Q

Cyanohydrin

A

CN + OH attatched to the same carbon

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7
Q

Aldehydes + ketones reacted with HCN will yield a —-

A

cyanohydrin

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8
Q

Wittig Reaction

A

reduces a ketone to an alkene

C=O bond to C=C bond

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9
Q

How do you form the wittig reagent/ ylide?

A

P(Ph)3 + alkly halide
pt
- SN2 like process, akyl halide must be primary or secondary

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10
Q

Where does the carbon of the new C=C bond come from in the wittig reaction?

A

the akyl halide reacting to form the ylide

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11
Q

Bayer Village oxidation

A

peroxyacetic acid + ketone or aldehyde to form a ester

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12
Q

What is the preference for where the oxygen is moved to for the bayer village reaction?

A

H>3>2>ph>1> methyl

left: easiest to move right: hardest to move

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13
Q

What is the suffix for compounds with one carb acid?

A

-oic acid

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14
Q

What is the suffix for compounds with two carb acids?

A

-dioic acid

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15
Q

What is the suffix for carboyxlate ions?

A

-oate

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16
Q

Why do carb acids have high bps?

A

because they can form two hydrogen bonds between each other

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17
Q

In water does the reaction favor a carb acid or H3O+?

A

carb acid bc it is weaker than H3O+ and reactions favor moving away from the strongest acid

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18
Q

Do halogens stabilize or de stabilize a carb acid?

A

stabilize, bc they are ewg

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19
Q

alkyne + O3 and H3O+ =

A

2 carboxlyic acids

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20
Q

primary alcohol + KMnO4/Chromic acid =

A

carboxylic acid

21
Q

Reagents and products of oxidation of an alkyl benzene

A

reagents: chromic acid +H2SO4
products: benzoic acid

22
Q

R-CN + H3O+ + heat =

A

carboxylic acid

new way to make carb acids

23
Q

CO2 + grignard reagent =

A

carboxlyic acid

a new way to make carb acids

24
Q

What reagents can be used to reduce a carb acid to an alcohol?

A

LAH or BH3 . THF and grignard reagent

25
Q

Mechanism of the reduction of carb acid to an alcohol

A
  1. pt to create carboxylate
  2. Elimination to form aldehyde intermediate
  3. nuc attack by H-
  4. pt to create neutral product
26
Q

Derivatives of carb acids

A

molecules that look like carb acids but the OH group has been replaced with something else

27
Q

What are the 5 carb acid derivatives we have been introduced to?

A
  1. acid halide
  2. acid anhydride
  3. ester
  4. amide
  5. nitrile
28
Q

suffix for acid halide

A

-yl halide

29
Q

suffix for acid anhydride

A

-anhydride

30
Q

suffix for amide

A

-amide

31
Q

Suffix for nitriles

A

-onitrile

32
Q

Nucleophilic acyl substitution

A

nucleophilic attack on a carb acid derivative to replace good LG

33
Q

What is the intermediate of Nucleophilic Acyl substitution?

A

tetrahedral intermediate

34
Q

What charges can form in acidic conditions?

A

positive or overall neutral

35
Q

What charges can form in basic conditions?

A

negative or over all neutral

36
Q

True or False?

C- and H- make good leaving groups because they are good nucleophiles?

A

false, they rarely make good leaving groups

37
Q

Where are the three places an extra pt step can occur in nucleophilic acyl substitution?

A
  1. before nuc attack
  2. between nuc attack and LLG
  3. after LLG
38
Q

Why would a pt step occur before nuc attack in nucleophilic acyl substitution?

A

If the reagents are acidic

39
Q

Why would a pt step occur between LLG and nuc attack in nucleophilic acyl substitution?

A

if the LG needs to be protonated in order to leave

40
Q

Why would a pt step have to occur after LLG?

A

if the nucleophile was neutral and the final product needs to be neutralized

41
Q

How do you prepare an acid chloride

A

treatment of a carb acid with SOCl2

42
Q

Hydrolysis of acid halides/ anhydrides

A

acid halide/ anhydride + water = carb acid +HCl

43
Q

alcoholysis of acid halides/anhydrides

A

ROH and pyridine + acid halide/anhydride = ester

44
Q

`

Aminolysis of acid halides/ acid anhydrides

A

2 eq of NH3 + Acid halide/anhydride = amide

45
Q

Why is pyridine not used in aminolysis of acid anhydrides/halides?

A

Bc NH3 is strong enough to neutralized HCl on its own

46
Q

Reduction of acid halides/ acid anhydrides

A

acid halide/anhydride + LAH or grignard reagent = alcohol

47
Q

What does LiAl(OR)3H do?

A

in a reduction of a acid halide/anhyrdie with LAH it will stop it at the aldehyde intermediate

48
Q

What does the Gilman reagent/R2CuLi do?

A

in the reduction of an acid halide/acid anhydride with a grignard reagent it will stop it at the ketone intermediate

Ochem 2 (7 decks)

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