ORGCHEM FINALS

called when a carbonyl group is attached to at least one H atom (RCHO)

called when a carbonyl group is attached to at least one H atom (RCHO)

aldehyde

called when a carbonyl group is attached to two carbon groups (RCOR)

ketone

(IUPAC) In naming aldehydes, Name the longest carbon chain by replacing the e in the alkane name with _____
Then we name and number substituents by counting the carbonyl group as carbon ___.

-al, 1

(Common names) In naming aldehydes, for the first four aldehydes, they use the prefixes:
__________ (1C)

___________(2C)

___________(3C)

___________(4C)
followed by __________

Form-

Acet-

Propion-

Butyr-

-aldehyde

Name this aldehyde

Methanal (formaldehyde)

Name this aldehyde

Ethanal (acetaldehyde)

Name this aldehyde

Propanal (propionaldehyde)

What are the aldehydes for these flavorings:
almonds: ______________
cinnamon: _______________

vanilla: _____________

benzaldehyde
cinnamaldehyde

vanillin

(IUPAC) In naming ketones, Name the longest carbon chain by replacing the e in the alkane name with _________;, the carbonyl group is indicated by _______-

-one, number

(COMMON NAME) In naming ketones, name by indicating the alkyl groups attached to the carbonyl group in __________ order, folllowed by ________.

alphabetical, ketone

Name this ketone

What are the common use of the ketone:
butanedione

as butter flavoring

Polar carbonyl

Polar carbonyl groups (does/does not) have H on the oxygen atom

does not

Polar carbonyl groups (can/cannot) form hydrogen bonds

cannot

Aldehydes and ketones have (polar/nonpolar) carbonyl groups

polar

Aldehydes and ketones have (attractions/repulsions) between polar groups

attractions

Aldehydes and ketones have (higher/lower) boiling points than alkanes and ethers of similar mass

higher

Aldehydes and ketones are (soluble/insoluble) in water

soluble

Aldehydes and ketones have electronegative _____ atoms in their carbonyl groups that form ______ bonds with water

Oxygen, hydrogen

Classify each as an 1) aldehyde or 2) ketone

Classify each as an 1) aldehyde or 2) ketone

Name the following compounds

Name the following compounds

Draw the condensed forms of these compounds

Indicate if each of the following is or is not soluble in water:

functional group that contains a carboxyl group, which is a carbonyl group (C═O) attached to a hydroxyl group (—OH)

carboxylic acid

carboxylic acid has the carboxyl group on carbon _____

1

In naming carboxylic acids,
for nonaromatics, identify the carbon chain containing the carboxyl group and replace the -e in the alkane name by __________

-oic acid

Give IUPAC name and Common name for each of the condensed structures:

Methanoic acid - Formic Acid

Ethanoic acid - Acetic acid

Propionic acid - Propionic acid

Butanoic acid - Butyric acid

The common names of simple carboxylic acids are:

________ (1C)

_________ (2C)

_________ (3C)

_________ (4C)

formic acid

acetic acid

propionic acid

butyric acid

The common names of carboxylic acids use letters ___, __, or __ to indicate locations of substituents

α, β, or γ

Alpha Hydroxy Acids (AHAs) occur naturally in ____, ____, and ______

fruit, milk, and sugarcane

______________ are used in skin care products

Alpha Hydroxy Acids

is the aromatic carboxylic acid

Benzoic acid

Benzoic acid locates substituents by assigning number ____ to the carbon attached to the carboxyl group

1

Benzoic acid has common names that assign the prefixes:

________ - 1,2 location

________ - 1,3 location

_________ - 1,4 location

ortho, meta, para

Give the IUPAC and common names for each of the following:

a. ethanoic acid (acetic acid)

b. 2-methylpropanoic acid (α-methylpropionic acid)

c. 2-bromobenzoic acid (o-bromobenzoic acid)

Give the IUPAC and common names for the following:

a. Propanoic acid (propionic acid)

b. 3-Methylbutanoic acid (β-methylbutyric acid)

c. 3-Bromobenzoic acid (m-bromobenzoic acid)

Carboxylic acids are prepared
> by oxidizing _______ or ___________

>from the oxidation of ______, which prodyces ethanoic acid (acetic acid)

primary alcohols or aldehydes
ethanol

What alcohol would be used to prepare the following:

1. Butanoic acid

2. Propanoic acid

Butanol
1-propanol

Carboxylic acids are (weakly/strongly) polar

strongly

Carboxylic acids have two (polar/nonpolar) groups:

hydroxyl (−OH) and carbonyl (C═O)

polar

The boiling points (bp) of carboxylic acids are (higher/lower) than those of alcohols, ketones, and aldehydes of similar mass

higher

The boiling points (bp) of carboxylic acids are high because they form _____ in which hydrogen bonds form between two polar carboxyl groups

dimers

Carboxylic acids form ________ bonds with many water molecules

hydrogen

Carboxylic acids with __________ carbon atoms are very soluble in water

1-4

Carboxylic acids are (strong/weak) acids

They ionize in water to produce ___________ ions and __________ ions

weak

carboxylate, hydronium

Carboxylic acids have (large/small) Ka values

small

Carboxylic acids exist mostly as ____________ and a few ions in aqueous solutions

molecules

Carboxylic acid salts are a product of a carboxylic acid with a ______ base

strong

Carboxylic acid salts are used as ________ and _________ enhancers

preservatives, flavor

Write the equation for the reaction of propanoic acid with:
a. water

b. KOH

a. water

CH3—CH2—COOH + H2O <====> CH3—CH2—COO– + H3O+

b. KOH
CH3—CH2—COOH + KOH <==> CH3—CH2—COO– K+ + H2O

In an ester, the H in the carboxyl group is replaced with an _______ group

alkyl

is the reaction of a carboxylic acid and alcohol in the presence of an acid catalyst to produce an ester

Esterification

Write the equation for the reaction of propanoic acid and methanol in the presence of an acid catalyst.

is used to relieve pain and reduce inflammation (w/chemical name)

Aspirin (Acetylsalicylic acid)

Aspirin is an ester of ________ and ___________

salicylic acid and acetic acid

is used to soothe sore muscles (w/chemical name)

Oil of wintergreen (Methyl salicylate)

Oil of wintergreen is an ester of ________ and _________

salicylic acid and methanol

What is flavor/odor does propyl ethanoate (propyl acetate) pertain to?

Pears

What are the respective flavors/odors for these esters

Pears
Bananas
Oranges
Pineapples
Apricots

In naming esters,

The name of an ester contains the names of the ______ group from the alcohol

the carbon chain from the acid with _____ending

alkyl

-ate

Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears:

Propyl ethanoate
Propyl acetate

Name the following esters:

Methyl butanoate
Ethyl propanoate

Draw the condensed structural formula of the following esters:

The boiling points of esters are (higher/lower) than alkanes of similar mass

higher

The boiling points of esters are (higher/lower) than alcohols and carboxylic acids of similar mass because esters cannot form hydrogen bonds

lower

In acid hydrolysis, an ester reacts with water to produce a __________ and an ___________;

___________ is also required

carboxylic acid, alcohol

acid catalyst

Base Hydrolysis (also called _______________)

is the reaction of an ester with a strong _________
produces the ______ of the carboxylic acid and an alcohol

Saponification
base

salt

The base hydrolysis of long chain fatty acids produces acid salts called “____________”

soaps

A soap contains a nonpolar end that dissolves in _____________ and a polar end that dissolves in ____

A soap forms groups of soap molecules called ____ that dissolve in water and are washed away

non polar fats and oils, water

micelles

Write the condensed structural formulas of the organic products when methyl acetate reacts with:

_____ contain one or more alkyl groups bonded to the nitrogen atom

amines

Amines are classified by as _____, _______, and _______

primary, secondary, and tertiary

In a primary (1°) amine, ____ carbon group is bonded to the nitrogen atom.
A secondary (2°) amine has _____ carbon groups.
A tertiary (3°) amine has ___ carbon groups.

1

2

3

Simple amines are named with common names as ______

alkylamines

In naming of amines (IUPAC)

A.)

STEP 1 Name the longest carbon chain bonded to the N atoms as __________ by replacing -e of the alkane name with ________.
STEP 2 Number the carbon chain to locate the amine group and any substituents.

STEP 3 In a secondary or tertiary amine, use the prefix _____to name groups attached to the N atom.

alkanamines, -amine

N-

Give the common and IUPAC names, and classify each as primary, secondary, or tertiary.

1-Propanamine (IUPAC), 1°
Propylamine (common)

N,N-Dimethylethanamine (IUPAC), 3°|
Ethyldimethylamine (common)

Draw the condensed structural formula for each of the following:

A. 2-pentanamine

B. N-methyl-1-butanamine

The amine of benzene is called _____

aniline

Amine of benzene may have alkyl groups attached to N that use the prefix ____ and the _____ name

N-, alkyl

Give the common and IUPAC names for each of the following:

The boiling points of amines are
(higher/lower) than alkanes of similar mass

(higher/lower) than alcohols of similar mass

higher

lower

The polar N—H bond provides hydrogen bonding in ____ and ____ amines but not ____ amines classiifications

The polar N—-H bonds in amines (is/is not) as polar as the —OH in alcohols

primary, secondary, but not in tertiary

is not as polar

Amines are soluble in water if they have ______ carbons

and because the N atom in smaller amines forms _______ bonds with the polar O—H bond in water

1 to 5
hydrogen

Amines are ___________ bases that attract a H+ from H2O

to the N atom, and are (strong/weak) bases in water

Brønsted-Lowry
weak

it is formed when amine is neutralized by an acid

amine salt

amine salts are named by replacing the amine part of the name with _______ followed by the name of the negative ion

ammonium

Amine salts are

(solid/liquid/gas/vapor) at room temperature

(soluble/insoluble) in water and body fluids

the form used for _____

solid

soluble

gas

is sold illegally as an amine salt

Cocaine

Cocaine is reacted with ______ to produce the free amine form known as “crack”

NaOH

is a cyclic organic compound

has a five- or six-atom ring

contains one or more nitrogen atoms

heterocyclic amine

Piperidine

Pyrrolidine

Pyrolle

are physiologically active nitrogen-containing compounds; produced by plants

Alkaloids

used as stimulants, anesthetics, and antidepressants, often habit forming

Alkaloids