Chapter 16 ketones and aldehydes Flashcards
Oxidation of a primary alcohol results in an _____
aldehyde
Oxidation of a secondary alcohol results in a _____
ketone
Reduction of an aldehyde results in an ______
alcohol
Oxidation of an aldehyde results in _________
carboxylic acid
Aldehydes and ketones are ______ polar.
moderately
Aldehydes and ketones ____ hydrogen bond with each other.
cannot
Aldehydes and ketones have higher boiling points than _____.
Alkanes
Common aldehydes and ketones normally take the form of _______.
liquid
Boiling points
_______> aldehydes/ketones>_____
alcohol> aldehydes/ketones/alkanes
Simple aldehydes and ketones are/arent water soluble?
They are water soluble
_______ are good solvents.
ketones
Many aldehydes and ketones have ______ odors.
distinct
Ketones/aldehydes with fewer than _ or _ carbon atoms are soluble in water.
5 or 6
Simple ketones are _____ solvents because they dissolve _____ and ______ compounds.
excellent, they dissolve polar and non polar compounds.
What compound is a good insect repellent, is used in perfumes and is found in lemon grass oils.
citronellal
What compound is the cinnamon flavor in foods, drugs, and is found in cinnamon bark?
Cinnamaldehyde
What compound is a moth repellent found in the camphor tree?
camphor
What compound has a musky odor in perfumes, and is found in the scent gland of the civet cat?
Civetone
CH2O or HCHO is the structure of what compound?
formaldehyde
What compound was the first synthetic plastic polymer of phenol and formaldehyde?
Bakelite
What formaldehyde polymers are now more widely used than bakelite?
urea
_____ polymers release _____ in the air, and is toxic.
CH2O
What compound is a sweet smelling narcotic?
Acetaldehyde
What compound is sweet smelling, flammable, found in fruits, and is produced in the break down of carbs in the body.
Acetaldehyde
Large doses of ______ can cause respiratory failure, chronic exposure can result in symptoms similar to alcoholism.
Acetaldehyde
What is produced in the liver during ketosis, and is also the most widely used solvent?
Acetone
In aldehyde oxidation, the hydrogen bonded to the carbonyl group is replaced by a _____ group.
OH-
Ketones do not react with ______ oxidizing agents.
mild
To distinguish between aldehydes and ketones, a ______________ agent can be used as a test.
Mild oxidizing agent
________ reagent consists of a solution containing silver in an aqueous ammonia
Tollens
Treatment of an ________ with Tollens reagent rapidly yields the carboxylic acid anion and metallic silver.
Aldehyde
________ reagent contains blue copper(II) ion, which is reduced to give a precipitate of red copper (I) oxide in the reaction with an aldehyde.
Benedicts reagent
______ reagent does not distinguish between ketones and aldehydes.
Benedicts
What reagent was extensively used as a test for sugars in urine?
Benedicts reagent
_______ are reduced to produce primary alcohols.
Aldehydes
Ketones are reduced to _______.
Secondary alcohols
In biological systems, the reducing agent for a carbonyl group is the coenzyme _________________.
Nicotinamide adenine dinucleotide (NAD+)
NAD can be a reducing agent, which is symbolized by _______
NADH
NAD can also be an oxidizing agent which can be symbolized by ______.
NAD+
How can NAD be an oxidizing agent and reducing agent?
By the loss and gain of a hydride ion
Initial product of addition reactions of aldehydes and ketones with alcohols are known as ______.
Hemiacetals
________ have both an -OH group and an -OR group bonded to the same carbon atom.
Hemiacetals
_______ forms hemiacetals with aldehyde and acetone.
ethanol
How do hemiacetals revert back to aldehydes or ketones?
The loss of an alcohol and establishment of equilibrium
When equilibrium is reached, how much hemiacetal is present?
Very little
When an alcohol and carbonyl functional groups are part of the same molecule that is reacting, the result is a ______ hemiacetal
cyclic
Which are more stable, cyclic hemiacetals or noncyclic?
Cyclic
Most simple sugars exist mainly in the __________ form.
cyclic hemiacetal
If a small amount of acid catalyst is added to the reaction of an alcohol or ketone, the hemiacetal initially formed is converted to an _____ in a ______ reaction.
Acetal in a substitution reaction
A _______ is a compound that has 2-OR groups bonded to what used to be the carbonyl carbon atom.
Acetal
Reversing the reaction in which an aldehyde or ketone forms an acetal, requires ______ and ______.
acid catalyst and a large quantity of water
Regenerating the aldehyde/ketone from an acetal which is formed can be done through a process known as ______.
hydrolysis
___________ is a reaction in which a bond or bonds are broken and the -H and -OH of water add to the atoms of the broken bond.
Hydrolysis
C \ C=O / H
Aldehyde
C \ C=O / C
Ketone
Which has terminal carbons? aldehydes or ketones?
Aldehydes
To know you are naming an aldehyde or ketone what can you look for ?
C=O
Do aldehydes and ketones have hydrogen bonding?
No
The bond between C=O is _____.
Polar
Since the bond between C=O is polar, how will this affect both the solubility and boiling points?
The boiling points and solubility will be higher
Aldehydes and ketones have no ______ bonding.
hydrogen bonding
When a carbonyl group is oxidized it results in a ___________.
carboxylic acid
When an alcohol is oxidized it becomes a ______ group.
carbonyl
Addition of alcohols results in _______ and _____.
hemiacetals and acetals
Hemiacetals and acetals are associated with _____.
carbohydrates.
Any compound containing the group C=O is considered a _______ compound.
carbonyl
What functional group has a C atom joined to an O atom by a double bond?
Carbonyl group.
How many electrons are shared in a double bond?
four
What degree is the angle between substituents in a carbonyl group carbon?
120
what carbonyl compound does this represent
O
||
R-C-O-H
Carboxylic acid
What compound has a carbonyl group bonded to at least one hydrogen?
Aldehyde
What compound has a carbonyl group bonded to two carbons in organic groups that can be the same or different?
Ketone
CH3CHO is representing a ______.
Acetaldehyde
CH3COCH3 is representing an ______.
Acetone
O
||
H - C - H
Formaldehyde
O
||
H3C-C-H
Acetaldehyde