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CHEM 353 > Ch. 18 > Flashcards

Ch. 18 Flashcards

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1
Q

What is the product of this reaction?

A

acetal formation

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2
Q

What is the product of this reaction?

A

cyanohydrin formation

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3
Q

What is the product of this reaction?

A

conjugate addition

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4
Q

What is the product of this reaction?

A

nitrile heterolysis

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5
Q

Which types of nucleophiles do direct addition? (1,2)

A

organometallics and hydrides

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6
Q

Will NaCN do direct addition or conjugate addition?

A

conjuage addition (1,4)

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7
Q

what is the purpose of a catalyst?

A

to decrease activation energy and increase the reaction rate

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8
Q

What do you need for an acid catalyzed formation of an acetal?

A

a weak nucleophile in excess (H2O, CH3OH, alcohols, etc)

an acid catalyst (H2SO4, HCl, etc)

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9
Q

Will acetals form in basic conditions?

A

No

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10
Q

how do you reverse the formation of an acetal?

(acetal –> carbonyl)

A

add H2O in excess

(this is a hydrolysis reaction)

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11
Q

do weak nucleophiles prefer direct (1,2) or conjugate (1,4) addition?

A

conjugate (1,4)

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12
Q

What is the product of this reaction?

A

imine/hydrazone/oxime formation

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13
Q

What is the product of this reaction?

A

reductive amination

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14
Q

What is the product of this reaction?

A
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15
Q

What is the product of this reaction?

A

enamine formation

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16
Q

What is the product of this reaction?

A
17
Q

How can you reverse an imine?

A

add excess H2O under acidic conditions

18
Q

How do you identify a hemiacetal molecule?

A

Look for carbon atoms that are bonded to two oxygen atoms. If one of the two oxygen atoms is part of an OH group, the molecule is a hemiacetal.

19
Q

How do you identify an acetal molecule?

A

Look for carbon atoms that are bonded to two oxygen atoms. If both of the oxygen atoms are part of OR groups, the molecule is an acetal.

20
Q

What is the first step in an acid-catalyzed reaction?

A

proton transfer from the acid-catalyst

21
Q

What is the first step in the hydrolysis of nitriles under basic conditions?

(reversing nitriles)

A

the base will dissociate into X+ and OH-, the OH- will attack the partitally positive carbon

22
Q

What is the product of this reaction?

A

Wolff-Kishner Reduction

NOT TESTED ON MECHANISM

23
Q

What types of nucleophiles prefer conjugate additon? (1,4)

A

Weak Nucleophiles

(HCN, CH2CH3SH, NaCN)

24
Q

What is the first step in a base-catalyzed reaction?

A

The base (-OH) takes a proton off of the weak nucleophile to make it a strong nucleophile

i.e. a proton transfer from the nucleophile to the base

25
Q

What is the product of the following reaction?

A

an enamine

26
Q

What is the product of the following reaction?

A

nitrile –> primary amide

27
Q

What is the product of the following reaction?

A

Aldol Reaction

OH attaches to beta Carbon

CHEM 353 (5 decks)

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