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