Chapter 11

Question 1

Compounds that have a hydroxyl group attached directly to a benzene ring

Answer 1

Phenol

Question 2

The addition of water to a molecule, such as the addition of water to a molecule, such as the addition of water to an alkene to form an alcohol

Answer 2

Hydration

Question 3

A two-step process for adding the elements of water (H and OH) to a double bond in a Markovnikov orientation without rearrangements. An alkene reacts with mercuric acetate (or trifluoroacetate), forming a bridged mercurinium ion. Water preferentially attacks the more substituted side of the bridged ion, breaking the bridge and resulting, after loss of a proton, in an alcohol. Reduction with NaBH4 replaces the mercury group with a hydrogen atom, yielding the final product

Answer 3

Oxymercuration-demercuration

Question 4

A compound with the formula ROSO2R’ and considered to be derivatives of sulfonic acids, HOSO2R’. Sulfonate esters are used in organic synthesis because of the excellent leaving group ability of the fragment -OSO2R’

Answer 4

Sulfonate ester

Question 5

A methanesulfonate ester. Methanesulfonate esters are compounds that contain the CH3SO3- group, i.e., CH3SO3R

Answer 5

Mesylate

Question 6

A p-toluenesulfonate ester, which is a compound that contains the p-CH3C6H4SO3 group, i.e., p-CH3C6H4SO3R

Answer 6

Tosylate

Question 7

A trifluoromethanesulfonate ester, which is a compound that contains the CF3SO3- group, i.e., CF3SO3R

Answer 7

Triflate

Question 8

The synthesis of an ether by the SN2 reaction of an alkoxide ion with a substrate bearing a suitable leaving group (often a halide, sulfonate, or sulfate)

Answer 8

Williamson ether synthesis

Question 9

A group that is introduced into a molecule to protect a sensitive group from reaction while a reaction is carried out at some other location in the molecule. Later, the protecting group is removed. Also called blocking group

Answer 9

Protecting group

Question 10

Conversion of an alcohol, R-OH, to a silyl ether (usually the form R-O-SiR’3, where the groups on silicon may be the same or different). Silyl ethers are used as protecting groups for the alcohol functionally

Answer 10

Silyl ether (silylation)

Question 11

A salt in which the cation is a species containing a positively charged oxygen

Answer 11

Oxonium salt

Question 12

An oxirane. A three-membered ring containing one oxygen and two carbon atoms

Answer 12

Epoxide

Question 13

An acid with the general formula RCO3H, containing an oxygen-oxygen single bond

Answer 13

Peroxy acid (peracid)

Question 14

The process of synthesizing an epoxide. Peroxycarboxylic acids (RCO3H) are reagents commonly used for epoxidation

Answer 14

Epoxidation

Question 15

The installation of hydroxyl groups at adjacent carbons and on opposite faces of an alkene, often accomplished by ring-opening of an epoxide

Answer 15

Anti 1,2-dihydoxylation

Question 16

Cyclic polyethers that have the ability to form complexes with metal ions. Crown ethers are named as x-crown-y where x is the total number of atoms and y is the number of oxygen atoms in the ring

Answer 16

Crown ether

Question 17

A reaction using a reagent that transports an ion from an aqueous phase into a nonpolar phase where reaction takes place more rapidly. Tetra-alkylammonium ions and crown ethers are phase-transfer catalysts

Answer 17

Phase transfer catalysis (catalyst)