10/29 Flashcards

1
Q

what is the disadvantage of friedel crafts alkylation

A

polyalkylation and rearrangement

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2
Q

what is the solution to rearrangement in F-C Alkylation

A

clemmenson reduction reduces a carbonyl to a alkane with Zn/Hg, HCl

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3
Q

in the clemmenson reduction, which carbon is being reduced

A

the benzyilic position

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4
Q

what if our molecule is sensitive to acid? what can we reduce a f-c acylation with

A

the wolf kishner reduction with hydrazine (N2H4, KOH and heat)

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5
Q

whats the difference between the clemmenson reduction and the wolf kishner

A

clemmenson occurs under acidic conditions, wolf kishner occurs under basic conditions

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6
Q

whats the reactive intermediate formed in a friedel crafts alkylation

A

carbocation

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7
Q

what source of carbocation is needed for an alkylation

A

any source of carbocation works

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8
Q

what are other sources of carbocations

A

protonation of an alkene with an acid, acid base reactions

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9
Q

why does BF3 act as a lewis acid

A

it is e poor because it has an empty p orbital (sp2) that can be filled

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10
Q

when reacting with an ortho para activator, what products are formed

A

both products are formed DRAW BOTH

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11
Q

what are the reactions of aldehydes and ketones

A

nucleophilic addition

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12
Q

what are the reactions of carboxylic acid derivatives

A

nucleophilic substitution

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13
Q

what are aldehydes called when they are substituents

A

they are called formyl groups

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14
Q

what is a two carbon carbonyl substituent called

A

a acetyl group

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15
Q

how do you get an aldehyde from a primary alcohol

A

PCC or swern

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16
Q

how do you get a ketone from a secondary alcohol

A

PCC or swern

17
Q

what does ozonoloysis do (O3, Me2S)

A

cleaves an alkene to make ketones and aldehydes

18
Q

why is DIBAL-H favorable to get a aldehyde in comparison to LAH

A

it is a weaker reducing agent and will not reduce all the way

19
Q

why is DIBAL-H weaker

A

it is sterically hindered and less reactive

20
Q

where can the nucleophile attack on a carbonyl in nucleophilic addition? what will it form

A

it can attack above and below the plane because it is sp2 trigonal planar. If the molecule is chiral it will form a racemic mixture

21
Q
A