Organic chemistry exam 1

Alkyl halides

are organic compounds containing a carbon atom bonded to a halogen atom (F, Cl, Br, I). They are derived from alkanes by replacing one or more hydrogen atoms with halogen atoms.

Alcohol

are organic compounds that contain one or more hydroxyl (-OH) functional groups. They are derived from alkanes by replacing a hydrogen atom with a hydroxyl group.

Ethers

are organic compounds that contain an ether functional group, characterized by an oxygen atom bonded to two alkyl or aryl groups. They are commonly formed by the reaction of alcohols with acids.

Sulfides

are organic compounds containing a sulfur atom bonded to two alkyl or aryl groups. They are analogous to ethers but with sulfur replacing the oxygen.

Thiol

are organic compounds that contain a sulfur-containing functional group, characterized by a thiol (-SH) group attached to an alkyl or aryl group. They are known for their strong odors and are often found in biological systems.

Amines

are organic compounds that contain a nitrogen atom bonded to one or more alkyl or aryl groups. They can act as bases and are commonly derived from ammonia.

Ketone

is an organic compound containing a carbonyl group (C=O) bonded to two alkyl or aryl groups. Ketones are commonly used as solvents and in the production of various chemicals.

Aldehyde

is an organic compound containing a carbonyl group (C=O) bonded to at least one hydrogen atom and one alkyl or aryl group. Aldehydes are often used in the synthesis of other organic compounds and have distinctive odors.

Carboxylic acid

is an organic compound that contains a carboxyl group (-COOH), which consists of a carbonyl and a hydroxyl group. Carboxylic acids are known for their acidic properties and are commonly found in nature, such as in fatty acids and amino acids.

Ester

is an organic compound formed from the reaction of a carboxylic acid and an alcohol, characterized by the functional group -COO-. Esters are often used in fragrances and flavorings due to their pleasant aromas.

Amides

are organic compounds that contain a carbonyl group (C=O) bonded to a nitrogen atom. They are derived from carboxylic acids and are commonly found in proteins and pharmaceuticals.

Acid chlorides

are reactive organic compounds derived from carboxylic acids, characterized by the presence of a carbonyl group (C=O) bonded to a chlorine atom. They are commonly used in the synthesis of esters and amides.

Nitrile

is an organic compound containing a cyano group (-C≡N) attached to a carbon atom. Nitriles are used in the production of plastics, pharmaceuticals, and as solvents.

Nitro

compounds are organic molecules that contain one or more nitro groups (-NO2) attached to a carbon atom. They are often used in explosives, dyes, and pharmaceuticals.

Constitutional isomers

Same formula but connectivity of atoms is different

Resonance

Same atoms and same connectivity

1. Only move electrons, never move atoms

2. Only move lone pairs or multiple bonds

Covalent bond

-2 elements from the same side of the periodic table

-sharing 2 electrons between nonmetals

Carbon with 3 bonds

+1 charge

Carbon with 4 bonds

0 charge

Carbon with 3 bonds and a lone pair

-1 charge

Nitrogen with 4 bonds

+1 charge

Nitrogen with 3 bonds and a lone pair

0 charge

Nitrogen with two lone pairs and two bonds

-1 charge

Oxygen with 3 bonds and one lone pair

+1 charge

Oxygen with 2 bonds and 2 lone pairs

0 charge

Oxygen with 3 lone pairs and one bond

-1 charge

what are the rules for picking the major resonance contributor structure

1. Contains more bonds and fewer charges

2. Better when all the atoms have octets

3. Negative charges are best placed on electronegative atoms

Sp hybridization

180 degrees and two groups around atom

Sp2

120 degrees and 3 groups around atom

Sp3

109.5 degrees and 4 bonds

What has the most S character (sp, sp2 or sp3)

Least sp3 most is sp

Put these in increasing bond strength (sp3, sp2, and sp)

Sp3, sp2, sp

What is the longest? (Csp3, Csp2 and Csp)

Csp3 is the longest and Csp is the shortest

Bronsted-lowery acids

Contain a proton (the net charge may be zero (+), or (-)

Bronsted-lowery bases

Contain a lone pair of electrons or a pie bond (the net charge may be zero or (-))

Pka = ?

-logKa

The larger the Ka…

The smaller the pka

Smaller pka =>

Stronger acid

Larger pka=>

Weaker acid

A strong acid produces..

A weak (stable/less stable) CB

A weak acid produces a..

Strong (unstable/ reactive) CB

CB stability

Ability of the CB to deal with (stabilize) the negative charge

Charge on the larger atom

Identify of atom with charge base more stable

Charge is on the more electronegative atom

Identify of atom with charge base more stable if

Atomic size =

Larger atoms form more stable conjugate bases

Electronegativity=

More EN atoms form more stable conjugate bases

A base is more stable the closer the (-) charge (or lone pair) is to EN atoms

True

Resonance effects on CB stability

The greater the number of resonance structures you can draw the more stable the CB

Hybridization effects on CB stability

CB is more stable if lone pair is in smaller orbital (more “s” character)

Lewis acid

Electron pair accepter (electrophoile)

Lewis base

Electron pair donee (nuclcophile)

All Lewis bases have either

Lone pairs or pie bonds

All B-L acids are also Lewis acids

True

All B-L bases are also Lewis bases

True

All Lewis acids are B-L acids

False

Group 13 metals and transition metals often are Lewis acids, but not B-L acids

True

Sulfuric acid

Nitric acid

Hydrochloric acid

Carbonic acid

Acetic acid

Hydroxide

OH-

Acetate

Carbonate

Bicarbonate

Ammonia

NH3

Hydride

H-