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Carbohydrates are a family of chemical substances encompassing monosaccharides, combinations of monosaccharides, and their derivatives. Glucose is a small carbohydrate; cellulose is a long-chain polysaccharide. Deoxyribose illustrates why composition alone does not define the family: replacing a hydroxy group in ribose by hydrogen still leaves a carbohydrate. See IUPAC Gold Book: carbohydrates.

Many familiar monosaccharides have a molecular formula of the form ${\mathrm{C}}_n{\mathrm{H}}_{2n}{\mathrm{O}}_n$, equivalently ${\mathrm{C}}_n({\mathrm{H}}_2\mathrm{O}{)}_n$. This explains the historical name, “hydrate of carbon”, but does not mean the molecule consists of carbon mixed with intact water molecules. Nor is it a universal formula: deoxyribose has ${\mathrm{C}}_5{\mathrm{H}}_{10}{\mathrm{O}}_4$. The family is defined through chemical structure and relationships, not that ratio. See IUPAC's definition and origin of the name carbohydrate.

The useful surprise is the variety of roles obtainable from related building blocks. Glucose participates in metabolism, ribose forms part of RNA, and linked glucose units make structural cellulose in a plant cell wall. Understanding carbohydrates therefore connects cellular energy, molecular information, and material structure. See Alberts et al., Molecular Biology of the Cell: the chemical components of a cell.

Chain-growth termination removes the ability of a reactive chain carrier to continue the succession of growth steps.^[ref] Two illustrative outcomes have different molecule counts:The first joins the two chains into one inactive polymer molecule. The second leaves two inactive polymer molecules, as can occur when one chain end transfers hydrogen to the other instead of their ends joining. End-group chemistry is suppressed in these unit-count symbols; they are not complete molecular formulas. Losing two polymerization-active sites does not mean losing two chains or any incorporated monomeric units. A temporarily inactive, reactivatable site must not be counted as irreversible chain-growth termination.

A chemical formula uses symbols of chemical elements and numerical subscripts to record composition. In the molecular formula ${\mathrm{H}}_2\mathrm{O}$ of water, the subscript $2$ counts two hydrogen chemical atoms, and the omitted subscript after $\mathrm{O}$ means one oxygen chemical atom. A molecular formula describes one molecule; a chemical formula need not describe a discrete molecule.

Read a preceding coefficient separately from the subscripts. One ${\mathrm{H}}_2\mathrm{O}$ contains two hydrogen and one oxygen chemical atom; $2{\mathrm{H}}_2\mathrm{O}$ contains four hydrogen and two oxygen chemical atoms distributed between two water molecules. In ${\mathrm{H}}_2{\mathrm{O}}_2$, the second subscript instead puts two oxygen chemical atoms into each hydrogen peroxide molecule. Thus $2{\mathrm{H}}_2\mathrm{O}\ne {\mathrm{H}}_2{\mathrm{O}}_2$: the coefficient scales the whole chemical formula, while a subscript specifies its composition. See Flowers et al., Chemistry 2e, §2.4: chemical formulas.

For crystalline $\mathrm{NaCl}$, the chemical formula specifies a $1:1$ ratio of sodium ions ${\mathrm{Na}}^{+}$ to chlorine ions ${\mathrm{Cl}}^{-}$. Its formula unit is the accounting entity; the ordinary crystal is an extended arrangement of ions, rather than a collection of discrete $\mathrm{NaCl}$ molecules. Specifying the entity matters when assigning an amount of substance. See formula unit and 2.6 Ionic and Molecular Compounds (§2.6: ionic and molecular compounds).

A molecular formula gives an atom inventory, not the full arrangement of chemical bonds or the molecular geometry. For example, ${\mathrm{C}}_6{\mathrm{H}}_{12}{\mathrm{O}}_6$ counts six carbon, twelve hydrogen, and six oxygen chemical atoms in a glucose molecule, but does not specify the pattern shown by its Fischer projection. Different structures can share a molecular formula. This compact inventory is useful for chemical equation accounting precisely because it leaves the structural detail to other representations.

The choice of letters has an early explanation in Jöns Jacob Berzelius, Essay on the Cause of Chemical Proportions (1813–1814), §III, transcribed by Carmen Giunta: letters made chemical signs easier to write and print, and formulas compressed information about composition. His numerical notation differed from modern subscripts; the lasting idea was to make proportions readable in ordinary text.

A hydrogen bond is an attractive association involving a hydrogen attached to another chemical atom, and an accepting atom or group. In the IUPAC 2011 definition, the atom $X$ in $X-\mathrm{H}$ is more electronegative than hydrogen, and evidence of bond formation is required. The familiar strong examples use O–H or N–H groups, but restricting the concept to only nitrogen, oxygen and fluorine misses weaker cases. A short distance alone is not the entire definition.^[ref]

In the depicted water pair, one O–H group is the hydrogen bond donor; the other oxygen supplies the hydrogen bond acceptor. The solid O–H line denotes a covalent bond within a water molecule; the dotted H···O line denotes the hydrogen bond between them. One water molecule can play both roles in a larger arrangement because it has O–H groups and lone pairs.

This makes hydrogen bonds useful for understanding organization beyond a single molecular formula. They connect water molecules and contribute to protein folding and recognition between molecules. The same types of chemical atoms can support different associations depending on which donor and acceptor sites are exposed and how they are oriented. Alberts and colleagues discuss these noncovalent interactions in Molecular Biology of the Cell, the chemical components of a cell.

Hydrogen bonds are often directional, with an approximately straight donor–H–acceptor arrangement favourable in familiar cases; strength and preferred geometry depend on the system. The IUPAC definition uses converging experimental or theoretical evidence rather than one universal distance threshold. The author-hosted 2009 task-group draft, §§3.1–3.3 explains the definition and typical criteria leading to the recommendation.

Lipids are a chemically diverse family of chemical substances, conventionally associated with biological origin and solubility in nonpolar solvents. They include triglycerides, phospholipids, and cholesterol. The name does not specify one molecular formula, one repeating monomer, or one kind of polymer. Some lipids have both hydrophilic and hydrophobic regions rather than being uniformly nonpolar. See IUPAC Gold Book: lipids.

Structure explains the different jobs. A triglyceride has three fatty acid-derived acyl groups attached to glycerol and serves as an energy store. A typical glycerophospholipid instead combines two such chains with a phosphate-containing head, making it an amphiphile suited to a lipid bilayer. Cholesterol has a different structure and also contributes to cell membrane properties. Thus a lipid is a chemical building material, while a lipid bilayer is an organization of many molecules. See Clark, Douglas and Choi, Biology 2e, 3.3: lipid structures and functions.

A monomer is a chemical substance whose molecules can undergo polymerization and contribute units to the essential structure of a polymer. A monomer molecule is the individual reactant; its incorporated monomeric unit is the portion identifiable as derived from that reactant. Incorporation can change chemical bonds and release small byproducts, so the unit in the chain need not have the complete molecular formula of the feed molecule. See IUPAC: monomer molecule and IUPAC, A brief guide to polymer terminology: monomeric units.

Three different counts answer three different questions. Monomer molecules describe the feed; monomeric units trace that feed's contributions to the product; a constitutional repeating unit describes the smallest chemical pattern repeating along a regular chain. In Nylon 6,10, two different monomers supply one interior constitutional repeating unit,Its molecular formula is ${\mathrm{C}}_{16}{\mathrm{H}}_{30}{\mathrm{N}}_2{\mathrm{O}}_2$. The diamine feed is ${\mathrm{C}}_6{\mathrm{H}}_{16}{\mathrm{N}}_2$, and the diacid-chloride feed is ${\mathrm{C}}_{10}{\mathrm{H}}_{16}\mathrm{C}{\mathrm{l}}_2{\mathrm{O}}_2$; subtracting two $\mathrm{HCl}$ gives the interior-repeat budget. For a finite linear chain made from $n$ of each reactant, there are $2n-1$ joining connections, hence $2n-1$ formal $\mathrm{HCl}$ eliminations, rather than $2n$. One amine end and one acid-chloride end remain in that ideal unmodified chain. This is a stoichiometry check on the depicted reaction, not a claim that the washed experimental thread retains those ends. The reacting end-group chemistry is documented in Hammond, lecture 5, p. 4; the specified Nylon 6,10 reactant pair is reported in Polymer Day, nylon demonstration.

Ethene shows the reverse counting mismatch. One $\mathrm{C}{\mathrm{H}}_2=\mathrm{C}{\mathrm{H}}_2$ monomer molecule contributes a two-carbon $-\mathrm{C}{\mathrm{H}}_2-\mathrm{C}{\mathrm{H}}_2-$ monomeric unit to ideal linear polyethylene, without a small byproduct in that growth step. But the smallest constitutional repeating unit of its uniform backbone is just $-\mathrm{C}{\mathrm{H}}_2-$: a chain containing $m$ incorporated ethene monomeric units contains $2m$ such interior one-carbon repeats. End groups are additional bookkeeping. The frequently drawn $[-\mathrm{C}{\mathrm{H}}_2-\mathrm{C}{\mathrm{H}}_2-{]}_m$ is useful for tracing the feed, although it is not the smallest constitutional repeat. The minimum-pattern definition is given in IUPAC: constitutional repeating unit; the ethene growth chemistry is described by ^[ref].

A segment of a freely jointed chain or Gaussian chain instead belongs to a statistical model. It can represent many chemical bonds and several constitutional repeating units; its length and the segment count are chosen to describe chain conformation at the intended scale. The three-repeats-per-segment drawing in Figure "From two liquid layers to a Nylon 6,10 thread: monomers, a constitutional repeating unit, and statistical segments" is a deliberately arbitrary coarse-graining example, not a measured Kuhn length. Always state the counting convention before substituting a segment count for a degree of polymerization. This separation lets chemistry track which chemical atoms entered the material while statistical models track how the material bends and extends.

Stereochemistry studies the spatial arrangement of chemical atoms in molecules. A Fischer projection records this information at successive stereocenters, whereas a molecular formula only counts chemical atoms. See McMurry: representing carbohydrate stereochemistry.

In chemical usage, sugars commonly means small carbohydrates, including single-unit monosaccharides and two-unit disaccharides. Glucose, ribose, and deoxyribose are monosaccharides. Cellulose is instead a polysaccharide assembled from many glucose units. The distinction counts chemically linked units; it does not classify every carbohydrate by sweetness or biological role. See Clark, Douglas and Choi, Biology 2e, 3.2: carbohydrates.

A useful first description of a monosaccharide asks how many carbon chemical atoms it contains and what its open-chain structure is. Ribose is an aldopentose, a five-carbon aldehyde sugar; glucose is an aldohexose, with six carbon chemical atoms. A Fischer projection then records the stereochemistry, information missing from the molecular formula. See McMurry, Organic Chemistry, 25.1: carbohydrate classification.

Urea is the chemical compound with molecular formula ${\mathrm{CH}}_4{\mathrm{N}}_2\mathrm{O}$ and structure $({\mathrm{NH}}_2{)}_2\mathrm{CO}$. See the NIST Chemistry WebBook, urea: formula and structure. Concentrated urea is used to promote protein denaturation in the ribonuclease A refolding experiment.