# Drawing Organic Compounds

## Vocabulary

### acid anhydride

organic compound that contains two carbonyl groups (${\rm {C}{=}{O}}$) bound to the same oxygen atom with (RCO)2O stoichiometry

### acyl halide

organic compound that contains a carbonyl group (${\rm {C}{=}{O}}$) bound to one alkyl ($-{\rm {R}}$) fragment and one halogen atom, with ${\rm{RC}({=}O) X}$ or ${\rm {R}{-}{COX}}$ stoichiometry

### alcohol

hydrocarbon containing a hydroxyl functional group

### aldehyde

organic compound that contains a carbonyl group (${\rm {C}{=}{O}}$) bound to one alkyl ($-{\rm {R}}$) fragment and one hydrogen atom, with ${\rm{RC}({=}O) H}$ or ${\rm {R}{-}{COH}}$ stoichiometry

### alkane

hydrocarbon containing only ${\rm C{-}C}$ single bonds and hydrogen with CnH2n+2 stoichiometry

### alkene

hydrocarbon containing at least one carbon-carbon double bond (${\rm {C{=}C}}$) with CnH2n stoichiometry

### alkyl halide

organic compound that contains a halogen atom. The halogen atom can be classified as primary, secondary, tertiary, vinylic, or aromatic.

### alkyne

hydrocarbon that contains at least one carbon-carbon triple bond (${\rm {C{\equiv}C}}$) with CnH2n-2 stoichiometry

### amide

organic compound that contains a carbonyl (${\rm {C{=}O}}$) linked to nitrogen atoms through a ${\rm {C{-}N}}$ bond. It has a general ${\rm{RC}({=}O){NR}'R''}$ stoichiometry.

### amine

organic compound that is a derivative of ammonia (NH3), where one or more hydrogen atoms are replaced by alkyl or aryl units (R), forming ${\rm {N{-}R}}$ single bonds

### aromatic

uninterrupted planar ring of sp2 and/or p orbitals whose electron count adds up to $4n+2$, where $n=$ any positive integer. Benzene, C6H6, is the most common example.

### aryl

term that applies when a group is attached to an aromatic compound. ${\rm {C}_6{H}_5{-}{Br}}$ is an aryl bromide.

### bond-line formula

formula that shows the functional group(s) and carbon skeleton of the molecule without explicitly showing carbon or hydrogen (except those that are part of the functional group)

### carboxylic acid

compound that contains an alkyl or aryl group (R) attached to a carboxyl group ($-{\rm {COOH}}$)

### condensed formula

version of the Lewis structure where most or all of the bond dashes are omitted and common atoms are combined in a parenthesis, such as CH3(CH2)4CH3

### delocalization

bonding electrons or lone pairs are not localized on one atom but are spread over more than one atom

### epoxide

compound that contains a cyclic ether made of two carbons and an oxygen

### ester

organic compound that contains a carboxyl unit in which a hydrogen of the hydroxyl group is replaced by an alkyl or aryl group, giving it $\rm R{-} C({=} O){OR}'$ or ${\rm {R{-}{COOR}}}'$ stoichiometry

### ether

organic molecule containing an oxygen bound by two alkyl or aryl groups through ${\rm {C{-}O}}$ bonds

### functional group

group of atoms with specific physical, chemical, and reactivity properties

### ketone

organic compound that contains a carbonyl group (${\rm {C{=}O}}$) bound to two alkyl ($-{\rm {R}}$) fragments (which can be the same, R and R, or different, R and R′) with ${\rm{RC}({=}O)R}'$ or RCOR ′ stoichiometry

### Lewis structure

model that represents covalent bonds and nonbonding electrons with symbols, dots, and lines

### molecular formula

formula indicating the number of atoms of each type of element in a molecule

### nitrile

organic compound that has a carbon triple bonded to a nitrogen with RCN stoichiometry

### resonance

method that organic chemists use to depict the Lewis structures of organic molecules where electrons can be in two or more different places around fixed atoms

### resonance hybrid

weighted average of all of the multiple representations of Lewis structures for an organic molecule

### resonance stabilization

lowering of the overall energy of a molecule due to the delocalization of electrons as seen in its resonance structures

### resonance structure

one of two or more Lewis structures with multiple equivalent representations

### sulfide

organic molecule containing a sulfur bonded to two alkyl or aryl groups through ${\rm {C{-}S}}$ bonds

### thiol

organic compound derived from H2S, containing an alkyl or aryl group covalently linked to a sulfhydryl group, $-{\rm {SH}}$, through ${\rm {C{-}S}}$ bonds, with ${\rm {R{-}SH}}$ stoichiometry