Aldehydes and Ketones 1

You must add _______ to _______ in order to synthesize aldehydes from alcohols

(K2Cr2O7, special conditions or pyridium chlrochromate) RCH2-OH

In order to oxidize alcohol to form ketones, we must add ______ to ______

(NaOCl or K2Cr2O7), secondary alcohol

What do you add to a methylaromatic to synthesize aldehydes

1. CrO3, (CH3CO)2-O (This forms a geminal diacetate) 2. Add H2O, H+

α s the symbol for a substituent that is on the _____ carbon of a carboxylic acid.

2

β is the symbol for a substituent that is on the _____ carbon of a carboxylic acid.

3

γ s the symbol for a substituent that is on the _____ carbon of a carboxylic acid.

4

δ s the symbol for a substituent that is on the _____ carbon of a carboxylic acid.

5

How do we use friedal crafts acylation to form ketones (this method only produces ____

Add RCOCl, AlCl3 to an aromatic ring, armatic ketones (phenones) only

In order to reduce an acid chloride for synthesis of aldehydes, you must add _______ to ________

LiAlH(O-t-Bu)3, R-Cl-C=O

Whats the first step in the friedal crafts acylation for ketone synthesis

RCOCl gives Cl to AlCl3 forming RC(+)=O + AlCl4

meta toluic acid represents ____

a COOH on 1 position of benzene ring; CH3 on 3 position of benzene ring

Whats the common name of CH3-COOH

acetic acid

whats the common name for ketones

alkyl alkyl ketone

Name of CH3-CH2-CH2=O

butryaldehyde

Whats the common name of CH3-CH2-CH2-COOH

butyric acid

Whats the common name of CH3(CH2)8-COOH

capric acid

Whats the common name of CH3(CH2)4-COOH

caproic acid

Whats the common name of CH3(CH2)6-COOH

caprylic acid

When using friedal crafts for ketone synthesis, the method does not work on ________

deactivated rings (rings with groups that are deactivating)

How to derive name of ketone with phenyl group from carboxylic acid

drop -ic acid, add -ophenone

How to derive aldehyde common name from carboxylic acid

drop ic acid, add aldehyde

Whats the common name of H-COOH

formic acid

What method is used to form phenones

friedal crafts acylation

Out of all methods to form aldehydes and ketones, which methods can form aromatic compounds only

friedal crafts acylation (ketone), oxidation of methylaromatics (aldehydes)

Aldehydes/ketones are water (soluble/insoluble) except for carbons of 4 carbons or less

insoluble

In coupling RCOCl and R2CuLi for _____ synthesis, we replace _______ with ______

ketone, halogen, alkane

Whats the common name of CH3(CH2)10-COOH

lauric acid (oil of lauryl)

IUPAC for ketones: whats parent chain

longest carbon chain with carbonyl group

IUPAC for aldehydes: whats parent chain

longest carbon chain with carbonyl group (COOH)

whats the name of H2C=O

methanal

What are the different ways to synthesize aldehydes

oxidation of primary alcohols, oxidation of methylaromatics, reduction of acid chlorides

What are the different ways to synthesize ketones

oxidation of secondary alcohols, Friedal-Crafts acylation, coupling of R2CuLi with acid chlroide

whats condensed formula of phenylacetaldehyde

ph-CH2-CH=O

Whats the common name of CH3-CH2-COOH

propionic acid

If you have p-bromotoluene and add Cro3, CH3CO)2-O and then H2O, H+, you will get ________

replace CH3 on benzene with CHO

Whats the substitution made when we reduce acid chlorides

replace halogen with H

IUPAC for aldehydes: whats name ending

take alkane name, drop -e, add -al

IUPAC for ketones: whats name ending

take alkane name, drop -e, add -one (lowest number possible for carbonyl group)

T/F R cant be Ar on aldehydes and ketones

true

Whats the common name of CH3-CH2-CH2-CH2-COOH

valeric acid

For the synthesis of aldehydes, What happens if you oxidize the primary alcohol with a different oxidizing agent than the ones listed?

you will form R-COOH