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19 notecards = 5 pages (4 cards per page)

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Chapter 19: Aldehydes & Ketones

front 1

The suffix “__________” indicates an aldehydic group, and the suffix “__________” is used for ketones.

back 1

-al ; -one

front 2

The electrophilicity of a carbonyl group derives from __________________________ effects, as well as ____________________ effects.

back 2

resonence ; inductive

front 3

A general mechanism for nucleophilic addition under basic conditions involves two steps

1) nucleophilic attack

2) ________________________________

back 3

proton transfer

front 4

The position of equilibrium is dependent on the ability of the nucleophile to function as a ______________________________.

back 4

leaving group

front 5

In acidic conditions, an aldehyde or ketone will react with two molecules of alcohol to form an ____________________.

back 5

acetal

front 6

The reversibility of acetal formation enables acetals to function as ______________________________ groups for ketones or aldehydes. Acetals are stable under strongly ______________ conditions.

back 6

protecting ; basic

front 7

In acidic conditions, an aldehyde or ketone will react with a primary amine to form an __________________.

back 7

imine

front 8

In acidic conditions, an aldehyde or ketone will react with a secondary amine to form an ____________________.

back 8

enamine

front 9

In the Wolff-Kishner reduction, a hydrazone is reduced to an __________________ under strongly basic conditions.

back 9

alkene

front 10

__________________________________ of acetals, imines, and enamines under acidic conditions produces ketones or aldehydes.

back 10

hydrolisis

front 11

In acidic conditions, an aldehyde or ketone will react with two equivalents of a thiol to form a ____________________________.

back 11

thioacetal

front 12

When treated with Raney nickel, thioacetals undergo desulfurization to yield a ____________________________ group.

back 12

methylene

front 13

When treated with a hydride reducing agent, such as lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4), aldehydes and ketones are reduced to ______________________________.

back 13

alcohols

front 14

The reduction of a carbonyl group with LiAlH4 or NaBH4 is not a reversible process, because hydride does not function as a ________________________________________.

back 14

leaving groups

front 15

When treated with a Grignard reagent, aldehydes and ketones are converted into alcohols, accompanied by the formation of a new ______________________ bond.

back 15

C-C

front 16

Grignard reactions are not reversible, because carbanions do not function as ____________________________________.

back 16

leaving groups

front 17

When treated with hydrogen cyanide (HCN), aldehydes and ketones are converted into ____________________________. For most aldehydes and unhindered ketones, the equilibrium favors formation of the ____________________________________.

back 17

cyanohydrins ; cyanohydrin

front 18

The Wittig reaction can be used to convert a ketone to an __________________.

back 18

alkene

front 19

A Baeyer-Villiger oxidation converts a ketone to an ____________________ by inserting __________________________________________ next to the carbonyl group. Cyclic ketones produce cyclic esters called ______________________________.

back 19

ester ; an Oxygen atom ; lactones