Organic Chemistry - Aldehydes And Ketones (Ch. 19)

Front 1

_______ are easily oxidized to yield ______ _____, but ________ are generally inert toward oxidation.

Back 1

Aldehydes, carboxylic acids
ketones

Front 2

Esters can be partially reduced to yield aldehydes by using:

Back 2

1. diisobutylaluminum hydride (DIBAH), toluene, -78 deg. Celsius
2. H3O+

Front 3

A Grignard reagent adds to the carbonyl oxygen of an aldehyde or ketone, making the carbonyl group a better _______.

Back 3

electrophile

Front 4

The systematic name for methanal is:

Back 4

formaldehyde

Front 5

For cyclic aldehydes in which the -CHO group is directly attached to a ring, the suffix ______ is used.

Back 5

-carbaldehyde

Front 6

The systematic name for ethanal is:

Back 6

acetaldehyde

Front 7

A neutral amino alcohol is called a ______

Back 7

carbinolamine

Front 8

The systematic name for benzencarbaldehyde is:

Back 8

benzaldehyde

Front 9

Imines are often called ____ _____ in many biological pathways.

Back 9

Schiff bases

Front 10

A nitrile (R-C(triplebond)N) can be reduced with LiAlH4 to yield a ______ _______ and can be hydrolyzed by hot aqueous acid to yield a _______ ______.

Back 10

primary amine, carboxylic acid

Front 11

Two methods of aldehyde synthesis include:

Back 11

oxidation of primary alcohols and oxidative cleavage of alkenes

Front 12

Ketones are named by replacing the terminal -e of the corresponding alkane with ____.

Back 12

-one

Front 13

Addition of hydride ion to aldehydes or ketones yields _____.

Back 13

alcohols

Front 14

Ketones undergo a slow cleavage reaction when treated with:

Back 14

1.KMnO4 in H2O and NaOH
2. H3O+

Front 15

Aldehyde oxidations occur through intermediate ______ or _______, which are formed by a reversible nucleophilic addition of water to the carbonyl group.

Back 15

1,1-diols
hydrates

Front 16

Methyl ketones are prepared by hydration of terminal alkynes with the reagents:

Back 16

H3O+ in HgSO4

Front 17

Aldehydes and ketones react reversibly with ___________________ to yield acetals (R2C(OR')2), called ketals if derived from ketones.

Back 17

2 equivalents of an alcohol in the presence of an acid catalyst

Front 18

Ozonolysis of alkenes yields ketones (if one of the unsaturated carbon atoms is disubstituted) using the reagents:

Back 18

1. O3
2. Zn/H3O+

Front 19

Aldehydes and ketones react with water in a reversible reaction to produce ____, or _____ diols

Back 19

1,1-diols
geminal

Front 20

Primary alcohols can be oxidized into aldehydes by using:

Back 20

PCC (pyridinium chlorochromate) in CH2Cl2

Front 21

Aldehydes and unhindered ketones undergo a nucleophilic addition reaction with HCN to yield ______.

Back 21

cyanohydrins, RCH(OH)C(triplebond)N

Front 22

Reaction of an aldehyde or ketone with a secondary amine yields an _____, while reaction with a secondary amine yields an _______.

Back 22

imine, enamine

Front 23

Aldehydes are named by replacing the terminal -e of the corresponding alkane name with:

Back 23

-al

Front 24

Secondary alcohols can be oxidized by a variety of reagents such as ______ and ______ to give ketones.

Back 24

PCC (pyridinium chlorochromate) in CH2Cl2
CrO3/H+

Front 25

Aldehydes can be oxidized by ______ _____ without harming carbon-carbon double bonds or other acid-sensitive functional groups in a molecule.

Back 25

Tollens' reagent (Ag2O) (in NH4OH and H2O)

Front 26

Secondary amines (R2NH) add to aldehydes and ketones to yield _____.

Back 26

enamines (R2N-CR=CR2)

Front 27

Alkenes with at least one vinylic hydrogen undergo oxidative cleavage when treated with:

Back 27

1. O3 (ozone)
2. Zn, CH3CO2H

Front 28

The Wolff-Kishner reaction involves treatment of an aldehyde or ketone with ______________________ to produce an alkane.

Back 28

hydrazine (H2NNH2) in the presence of KOH.

Front 29

Aryl ketones are prepared by _________ acylation of an aromatic ring with an acid chloride in the presence of ______.

Back 29

Friedel-Crafts, AlCl3/heat

Front 30

The _____-catalyzed hydration reaction of water to an aldehyde or ketone begins with the nucleophilic hydroxide ion attacking the electrophilic carbonyl carbon, whereas the _____-catalyzed hydration reaction begins with protonation of the carbonyl oxygen atom.

Back 30

base, acid