Exam 4 chem 1451

isobutyl

(CH3)2CHCH2-

tert-butyl

(CH3)3C-

Meth-

1 carbon

Prop-

3 carbons

Ethylene

Ethene

iodo

I-

Ester structure

RCOOR

phenolate (or phenoxide) ion

The conjugate bases of a phenol

aniline

benzenamine

alkynes

have at least one triple bond between carbon atoms.

-one

ketone suffix

propionic acid

propanoic acid CH3CH2COOH

Dec-

10 carbons

Eth-

2 carbons

But-

4 carbons

Pent-

5 carbons

Hex-

6 carbons

Hept-

7 carbons

Oct-

8 carbons

Non-

9 carbons

Complete combustion reaction

A reaction in which O2 is added to a compound containing carbon and hydrogen, producing CO2 and H2O

-al

Aldehyde suffix

Haloalkanes

Alkanes with halogen substituents

substituent

An atom or group of atoms attached to the parent chain in a molecule. A molecule can have one or more substituents.

bromo

Br-

isopropyl

CH(CH3)2

methyl

CH3

ethyl structure

CH3CH2

propyl

CH3CH2CH2

butyl

CH3CH2CH2CH2-

sec-butyl

CHCH2CH3- | CH3

carboxylic acid

COOH

weak organic acids

Carboxylic Acid and Phenol donate a proton (H+), acting as a Brønsted-Lowry acid.

chloro

Cl-

Incomplete combustion reaction

Combustion in which not enough oxygen is supplied to completely burn the fuel. Carbon monoxide is a common product.

When the two higher-priority groups are positioned in opposite directions

E-configuration.

Acetylene

Ethyne (C2H2)

fluoro

F-

Alkenes

Hydrocarbons with one or more carbon-carbon double bonds

constitutional isomers.

Molecules which have the same molecular formula but are different due to different atomic connectivity

Conformations

One important feature of a single bond is its ability to rotate around the bond. Different shapes that a single molecule can take on because of bond rotations are called • They have the same molecular formula. • They have the same atomic connectivity. • They look different because of the rotation of one or more single bonds.

Rules for Naming Alkenes (or Alkynes)

Step 1 Identify the parent chain and the substituent(s) in a molecule and their name. Find the longest carbon chain containing the double bond (or the triple bond), and name the compound by using the suffix -ene (or −yne). Indicate the position of the double bond by giving the number of the first alkene carbon and placing that number immediately before the parent name. If more than one double bond is present, indicate the position of each and use one of the suffixes -diene, −triene, (or −diyne, −triyne) and so on. Step 2: Number the carbon atoms in the parent chain. Begin at the end nearer the double bond (or the triple bond) or if the double (or triple) bond is equidistant from the two ends, begin at the end nearer the first branch point. This rule ensures that the double-bond (or triple-bond) carbons receive the lowest possible number. Step 3: Number the substituents according to their positions in the chain. Step 4: Write the name as a single word. List the substituents alphabetically.

Rules for Naming Alkanes with Substituents

Step 1 Identify the parent chain and the substituent(s) in a molecule and their name. In order to name branched alkanes, you need to understand the concepts of the parent chain and a substituent. • The parent chain is the longest continuous chain of carbon atoms in a molecule. Only one parent chain exists in a molecule. • A substituent is an atom or group of atoms attached to the parent chain in a molecule. A molecule can have one or more substituents. Step 2 Number the atoms in the parent chain. If there is one substituent, the parent chain is numbered to give the substituent the lower number. If there are two or more substituents, number the parent chain from the end that gives the lower number to the substituent encountered first. Step 3 Number the substituents. Assign the number to each substituent according to its point of attachment to the parent chain. If there are two substituents on the same carbon, give them both the same number. Step 4 Write the name as a single word. Construct the name of the alkane by placing the alkyl groups in alphabetical order and specifying their position numbers, followed by the name of the parent chain. The labels di, tri tetra, etc., are added if two or more identical substituents are present. Don't use these prefixes for alphabetizing purposes. Separate numbers by using a comma, and numbers from letters by using a hyphen. Also, the prefix iso- is not hyphenated and is used for alphabetizing purposes, but the hyphenated prefixes sec- and tert- are not used for alphabetizing purposes.

carboxylate ion

The conjugate bases of a carboxlyic acid

weak organic bases

The lone pair on the nitrogen atom of an amino group can accept a proton (H+). Therefore, an amine can act as a Brønsted-Lowry base

Hydrogenation

When a hydrogen molecule (H2) reacts with an alkene or an alkyne compound, hydrogen atoms are added to each of the carbon atoms in the double bond of an alkene or the triple bond of an alkyne, converting the double bond or the triple bond into a single bond. hydrogen molecule acts as a reducing agent to reduce the alkene or alkyne to an alkane.

cis-configuration.

When the two alkyl groups are positioned in the same direction,

Z-configuration.

When the two higher-priority groups are positioned in the same direction,

Alkanes

a hydrocarbon containing only single covalent bonds

-ol

alcohol suffix

-amide

amide suffix

amine suffix

amine

Amine Salts

amines are bases, their reaction with an acid produces a salt

Cycloalkane

an alkane that is a ring or cyclic structure

Condensed Structural Formula

another way to write a large organic molecule.

wedge and dash notation

applied to organic compounds to represent a three-dimensional structure. Recall that a solid wedge is a bond coming out of the paper toward you and the dashed wedge is a bond behind the paper away from you. The solid line represents a bond that lies on the paper.

butyric acid

butanoic acid CH3CH2CH2COOH

methanetriyl group

carbon atom with exactly one attached hydrogen atom and three single bonds

methyl group

carbon atom with exactly three attached hydrogen atoms and one single bond

methylene bridge (methanediyl group)

carbon atom with exactly two attached hydrogen atoms and two single bonds

-oic acid

carboxylic acid suffix

alcohol

compound must be bonded to the hydroxyl (−OH) group

thiol

compound must be bonded to the the sulfhydryl (-SH) group

unsaturated hydrocarbons

contain double and/or triple bonds between carbon atoms. alkenes, alkynes, and arenes

Saturated hydrocarbons

contain only single bonds between carbon atoms Alkanes

Amide

derivative of a carboxylic acid in which the "-OH" of the carboxylic acid group is replaced with an "-NH2" group.

Ester

derivative of a carboxylic acid in which the "-OH" of the carboxylic acid group is replaced with an alkyl group.

Geometric Isomers of Alkenes

double bonds cannot rotate. The lack of rotation around the carbon-carbon double bond has the potential to. When identical groups are attached to a carbon atom on either side of a double bond, then are not possible. The Cis and Trans Notation. The E and Z Notation.

-oate

ester suffix

acetic acid

ethanoic acid CH3COOH

ether suffix

ether

primary alcohol

first oxidized to aldehyde, and then is further oxidized to a carboxylic acid.

Arenes (or aromatic compounds or aromatics)

hydrocarbons that are based on a benzene molecule. (Rings)

Phenol

hydroxybenzene

formic acid

methanoic acid HCOOH

Toluene

methylbenzene

Primary (1°) amine

nitrogen of an amino group bears only one alkyl group

Tertiary (3°) amine

nitrogen of an amino group bears three alkyl group

Secondary (2°) amine

nitrogen of an amino group bears two alkyl group

Hydrocarbons

organic molecules consisting of only carbon and hydrogen

secondary alcohol

oxidized to a ketone.

Oxidation of Alcohol

primary and secondary alcohols can be oxidized. occurs by removing one H atom from the hydroxyl (-OH) group and another H atom from the C atom bearing the -OH group. A tertiary alcohol cannot because no hydrogen atoms are connected to the carbon atom bearing the hydroxyl group.

condensation reaction

process in which two molecules are joined together by removing a small molecule (typically H2O).

Amide Formation Reactions (Amidation)

produced when a carboxylic acid reacts with ammonia or with an amine and eliminates a water molecule Because an amine (or ammonia) is a base, a reaction between a carboxylic acid and an amine (or ammonia) is an acid-base reaction and results in ammonium salt.

Structural Formula

shows all the bonds and atoms of the molecules.

numbering a carbon chain

smaller number is assigned alphabetically to the first substituent.

functional groups

specific arrangement of atoms in a molecule. It confers a molecule with particular physical and chemical properties.

Organic compounds

substances composed of carbon and hydrogen and a few other elements including nitrogen, oxygen, and sulfur. The simplest organic compound is methane (CH4).

The parent chain

the longest continuous chain of carbon atoms in a molecule. Only one exists in a molecule.

primary (1°) alcohol

the one alkyl group bonded to the carbon atom bearing the -OH group.

E and Z Notation

the positions of higher priority groups are compared instead of the positions of alkyl groups. higher priority is assigned to a longer alkyl group.

Molecular Formula

the simplest method to describe a molecule. It describes the types and the number of constituent atoms. For example, C3H8O. The formula describes that the molecule is made of three carbon atoms, eight hydrogen atoms and one oxygen atom.

tertiary (3°) alcohol

the three alkyl groups bonded to the carbon atom bearing the -OH group.

secondary (2°) alcohol

the two alkyl groups bonded to the carbon atom bearing the -OH group.

thiol suffix

thiol

trans-configuration.

two alkyl groups are positioned in opposite directions

Ester Formation Reaction (Fischer Esterification)

when a carboxylic acid and an alcohol react in the presence of an acid catalyst and eliminate a water molecule.

cis and trans notation

will not work when more than two alkyl groups are attached to a double bond

Line-Angle Formula (or Skeletal Formula)

• Covalent bonds are represented by lines. • Carbon atoms are not shown. You need to assume that a carbon atom appears where lines (bonds) meet and at the end of each line. • Hydrogen atoms are drawn only when attached to atoms other than carbon. • You need to assume that a hydrogen atom appears to give each carbon its required four bonds. • Draw explicitly all heteroatoms (atoms that are not carbon and hydrogen) and the hydrogen atoms directly attached to heteroatoms. • A double bond and a triple bond must be drawn as a double bond and a triple bond.