Characteristics of hydroxyl groups
1) hybridization and bond angle
2) how does the bond angle compare to the bond angle of water
The O-H bond lengths are about the same in water and methanol, but the C-O is __, reflecting the __ of carbon compared to hydrogen.
1) sp3/ 108.9
2) it is larger
3) because the methyl group is much larger than a hydrogen atom
larger covalent radius
One way of organizing the alcohol family is to classify each alcohol according to the type of __: the one bonded to the -OH group. If this carbon atom is __(bonded to one other carbon atom), the compound is a __.
carbinol carbon atom
A __ has the -OH group attached to the __ carbon atom, and a __ has it bonded to a __ carbon.
Compounds with a hydroxyl group bonded directly to an aromatic ring are called __, which have many properties similar to those of alcohols, while other properties derive from their __.
1) carries the __ suffix, together with a __ to give the hydroxyl's location.
2) What is the first rule for naming.
1) ol, number
2) find the longest carbon chain bearing the -OH group
The alcohol functional group takes __ over __ and __, so the chain is numbered in order to give the lowest possible number to the carbon atom bonded to the __ group
The -OH functional group is named as a __ when it appears on a structure with a higher-priority functional group or when the structure is too difficult to name as a simple alcohol..
Alcohols with two -OH groups are called __ or __. They are named like other alcohols except that the suffix __ is used and two numbers are needed.
The term glycol generally means __, or __, with its two hydroxyl groups on adjacent carbon atoms. __ are usually synthesized by the hydroxylation of alkenes, using peroxyacids, osmium tetroxide, or potassium permanganate.
Because the phenol structure involves a benzene ring, the terms __ (1,2-disubbed), __ (1,3-disubbed), and __ (1,4-disubbed) are often used in the common names.
The methylphenols are called __, while the names of the __ are based on their historical uses and sources rather than their structures.
Most of the common alcohols, up to about 11 or 12 carbons, are __ at room temp.
True or False: Lower molecular weight alcohols are liquids.
Such large difficerences in BPs of ethyl alcohol (78) and propane alochol (-42) suggests that __ are attracted to each other much more strongly than __ molecules. Two important intermolecular forces are responsible: _ and __.
__ is the major intermolecular attraction responsible for ethanol's hight BP. The hydroxyl hydrogen of ethanol is strongly __ by its bond to oxygen and it forms a __ with a pair of nonbonding electrons from the oxygen atom of another alocohol molecule.
Ethers have __ bonded to their oxygen atoms, so they have no O-H hydrogen atoms to form hydrogen bonds. __ have a strength of about 21 kJ per mole: weaker than typical __ of 300-500 kJ, but much stronger than __.
two alkyl groups
__ also contribute to the relatively __ of alcohols and ethers. The polarized C-O and H-O bonds and the nonbonding electrons add to produce a __ of 1.69 D in ethanol, compared with a __ of only 0.08 D in propane. In liquid ethanol, the positive and negative ends of these dipoles align to produce attractive interactions.
dipole moment x2
__ are clearly much stronger intermolecular attractions than __.
Walter and alcohols have similar properties because they all contain __ that can form H bonds. Alcohols form hydrogen bonds with water, and several of the lower-MW alcohols are __ (soluble in any proportions) with water.
Similarly, alcohols are much better __ than __ for polar substances. Significant amounts of ionic compounds such as NaCl can dissolve in some of the lower alcohols. We call the hydroxyl group __, meaning "water loving" because of its affinity for water and other polar substances
The alcohol's alkyl group is called __ because it acts like an alkane: it disrupts the network of hydrogen bonds nad dipole dipole attractions of a polar solvent such as water. The alkyl group makes the alcohol less __, yet it lends solubility in nonpolar organic solvents. As a result, most alcohols are miscible with a wide range of nonpolar organic solvents.
True or False: The water solubility increases as the alkyl group becomes larger.
False: decreases as the alkyl group becomes larger
alcohols with one, two, or three carbon alkyl groups are miscible
a four carbon is large enough that some isomers are not miscible, but tert butyl alcohol is miscible.
IN GENERAL: a hydroxyl gorup can carry about 4 carbon atoms into water
Like the hydroxyl proton of water, the hydroxyl proton of an alcohol is __. A strong base can remove the hydroxyl proton to give an __.
The acidities of alcohols vary widely, from alcohols that are about as acidic as water to some that are much less acidic. The __ of an alcohol is defined by the __.
acid-dissociation constant, Ka
The __ constants for alcohols vary according to their structure, from about 10^-16 for __down to about 10^-18 for most __.
Explain the trend in acidity.
the acidity decreases as the substitution on the alkyl group increases, because a more highly substituted alkyl group inhibits solvation of the alkoxide ion, decreasing the stability of the alkoxide ion and driving the dissociation equilibrium toward the left
__ are strong nucleophiles and strong bases. When an __ is needed in a synthesis, it is often formed by th reaction of __ or __ with the alcohol. This is an __, with the metal being __ and the H ion __ form hydrogen gas. __ bubbles out of the solution, leaving the sodium or potassium salt of the alkoxide ion.
alkoxide ions x2
The more acidic alcohols, like methanol and ethanol, react rapidly with sodium to form __ and __. __ react more slowly. __ react very slowly with sodium. __ is often used with secondary and tertiary alcohols because it is __, and the reaction can be completed in convenient amount of time.
more reactive than sodium
Some alcohols react slowly with both __ and __ In these cases, a useful alternative is __, often is tetrahydrofuran (THF) solution. __ reacts quickly to form the __, even with different compounds.
sodium hydride x2
True or False: Phenols have the same acidity as cyclohexanols.
Phenols are nearly 100 million times more acidic than cyclohexanol
Cyclohexanol is a typical __, with a typical acid-dissociation constant for an __. There must be something special about phenol that makes it unusually __. The __ is more stable than a typical __ because the negative charge is not confined to the oxygen atom but is delocalized over the __ and __ of the ring.
three carbon atoms
A large part of the negative charge in the __ still resides on the __, since it is the most __ of the four atoms sharing the charge. But the ability to spread the negative charge over four atoms rather than concentrating it on just one atom produces a more stable ion. The reaction of phenol with __ is __.
__ are prepared simply by adding hte __ to an aqueous solution of __ or __. There is no need to use __ or __. __ was once called __ because of its ability to __ common bases.