Alcohols and Hydroxyl Groups Quiz

A compound with an -OH group attached to a saturated carbon atom. They are important solvents and intermediates in chemical synthesis.

Alcohols classified based on the number of carbon atoms directly bonded to the carbon atom bearing the -OH group.

A compound with an -OH group directly attached to a carbon atom in a benzene ring.

The strongest type of intermolecular attraction, which is formed between a hydrogen atom covalently bonded to a highly electronegative atom (O or N) and a lone pair of electrons on another electronegative atom.

The ability of a substance to dissolve another substance. Alcohols are good solvents due to the presence of the polar -OH group, which allows them to interact with both polar and nonpolar molecules.

The process of breaking down complex molecules into simpler molecules. Alcohols are important in chemical synthesis because they can react with various reagents to form a wide range of products.

The boiling point of a substance is the temperature at which it changes from a liquid to a gas. Alcohols have higher boiling points than similar alkanes and alkyl halides due to the presence of hydrogen bonding, a strong intermolecular force.

The process of naming compounds according to a set of rules. In IUPAC nomenclature, the longest chain containing the hydroxyl group is identified and numbered from the end nearer the hydroxyl group.

Alcohols are weakly basic and weakly acidic, acting as weak Brønsted bases. They can be protonated by strong acids to form positively charged oxonium ions.

Alcohols and phenols can donate a proton to water, though to a very small extent, forming hydronium ions and alkoxide or phenoxide ions.

The acidity constant, Ka, measures the extent to which a Brønsted acid donates a proton to water. pKa, its logarithmic form, is directly proportional to the equilibrium's free energy, making it easier to compare acid strengths.

Simple alcohols have similar acidity to water. The addition of alkyl groups makes them weaker acids, while better solvation of the alkoxide ion by water favors its formation. Steric effects also play a role.

Electron-withdrawing groups stabilize the negative charge of the alkoxide ion, making the alcohol a stronger acid. They pull electron density away from the O-atom.

Alkoxides are formed by reacting alcohols with strong bases like sodium hydride (NaH), sodium amide (NaNH2), or Grignard reagents. They act as bases and are important reagents in organic chemistry.

Alcohols can be converted to many functional groups, making them versatile starting materials in organic synthesis.

Hydroboration/oxidation and oxymercuration/reduction are two methods of converting alkenes to alcohols. The former provides syn addition and anti-Markovnikov regiochemistry, while the latter gives Markovnikov regiochemistry.

Cis-1,2-diols are formed by dihydroxylation of alkenes using OsO4 followed by NaHSO3 reduction. Trans-1,2-diols are formed by acid-catalyzed hydrolysis of epoxides.

Reduction of carbonyl compounds with reagents like sodium borohydride (NaBH4) or lithium aluminum hydride (LiAlH4) produces alcohols.

NaBH4 is a mild, moisture-tolerant reagent, while LiAlH4 is more powerful but reactive with water. Both add the equivalent of a hydride ion (H-) to the carbonyl compound.

Grignard reagents, formed by reacting alkyl, aryl, or vinylic halides with magnesium, react with carbonyl compounds to yield alcohols.

Grignard reagents add to the carbonyl group, forming a new carbon-carbon bond and generating an alkoxide intermediate which is then protonated to produce the alcohol.

Alcohols can be converted to alkyl halides via SN1 or SN2 reactions. Tertiary alcohols react via SN1 through carbocation intermediates, while primary and secondary alcohols react via SN2 using reagents like SOCl2 or PBr3.

Dehydration of alcohols produces alkenes through the loss of a water molecule. The reaction involves removing the -OH group and a hydrogen atom from the neighboring carbon to form a double bond.

A functional group that reacts with chlorotrimethylsilane and base, forming a trimethylsilyl (TMS) ether. This protects the alcohol from unwanted reactions.

The process of removing a protecting group, restoring the original functional group. For TMS ethers, this is achieved with acid or fluoride ion.

A compound with two organic groups attached to the oxygen atom, with general formula R-O-R'.

A cyclic ether with four carbon atoms in the ring. It's commonly used as a solvent in organic reactions.

A reaction that forms ethers from a primary alkyl halide or tosylate and an alkoxide. The alkoxide is often prepared by reacting an alcohol with sodium hydride.

Forms ethers from alcohols and alkyl halides in one step using silver oxide as a catalyst.

A reaction involving an alkene, an alcohol, and mercuric acetate (or trifluoroacetate), followed by demercuration with NaBH4. It results in the addition of an alcohol across the alkene's double bond.

Ethers are relatively unreactive, but can be cleaved under strong acidic conditions at elevated temperatures. The less hindered component of the ether will form an alkyl halide.

A three-membered ring ether, often called an epoxide. Ethylene oxide is a key industrial intermediate.

A reaction where an alkene reacts with a peroxyacid to form an epoxide. This is a common pathway for epoxides.

A compound containing a hydroxyl group and a halogen on adjacent carbon atoms. It's an intermediate in epoxide formation.

The addition of water to an epoxide, in the presence of dilute acid. This opens the ring and forms a 1,2-diol (a molecule with two hydroxyl groups adjacent to each other).

Cyclic ethers with repeating -OCH2CH2- units. They are named as x-crown-y, where x is the number of atoms in the ring and y is the number of oxygen atoms.

Sulfur analogues of alcohols. They are named with the suffix '-thiol' and are excellent nucleophiles.

Sulfur analogues of ethers. They are named similar to ethers, replacing 'ether' with 'sulfide' or 'sulfide' with 'alkythio'