ch 5 - Alcohols

Question 1

hydroxyl group

Answer 1

-OH (formula of ROH for alcohols)

Question 2

alcohol as non-highest priority group

Answer 2

named as substituent, with prefix hydroxy-

Question 3

phenols

Answer 3

hydroxy groups attached to aromatic rings

Question 4

naming of substituents on phenols in relation to each other’s position

Answer 4

ortho (or o-): next to; meta- (or m-): separated by one carbon; para- (p-): on opposite sides of the phenol

Question 5

causes of hydrogen bonding

Answer 5

increased melting points, boiling points and solubility in water

Question 6

hydrogen bond

Answer 6

a hydrogen attached to highly electronegative atoms like nitrogen, oxygen or fluorine results in polarity; pulls electron density away from the less electronegative hydrogen atom (slightly positive H and slightly negative on other). Slightly positive H attracts partially neg of another molecule, generating this noncovalent force

Question 7

primary alcohols to aldehydes

Answer 7

proceeds via pyridinium chlorochromate (PCC) - a mild anhydrous oxidant

Question 8

geminal diols

Answer 8

1,1 - diols, produced from hydration of aldehydes

Question 9

secondary alcohols oxidized to ketones

Answer 9

proceeds with PCC or any stronger oxidizing agent

Question 10

primary alcohols to carboxylic acids

Answer 10

proceeds with strong oxidizing agent like chromium (VI), which is reduced to chromium (III) in the process (ex Na2Cr2O7 and K2Cr2O7); also CrO3

Question 11

secondary alcohols to ketones

Answer 11

Na2Cr2O7 or K2Cr2O7, or CrO3

Question 12

Jones oxidation

Answer 12

dissolving of a very strong oxidizing agent chromium trioxide (CrO3) with dilute sulfuric acid in acetone; oxidizes primary alcohols to carboxylic acids and secondary alcohols to ketones

Question 13

mesylate

Answer 13

good leaving group formed by the protonation or reaction of hydroxyl groups of alcohols. compound containing functional group -SO3CH3, derived from methanesulfonic acid; prepared using methysulfonyl chloride and an alcohol in the presence of a base; anionic form is a S with two double bonds to O, a single bond to O-, and a methyl. can serve as a protecting group

Question 14

tosylates

Answer 14

good leaving group formed by the protonation or reaction of hydroxyl groups of alcohols. contain the functional group -SO3C6H4CH3, derived from toluenesulfonic acid; produced by the reaction of alcohols with p-toluenesulfonyl chloride, forming esters of toluenesulfonic acid; form is a benzene with a methyl group para to a S double bonded on both sides to O, and bonded to O with an R group; can serve as a protecting group

Question 15

how alcohols are used as protecting groups

Answer 15

aldehydes/ketones reacted with two equivalents of alcohol (diol or dialcohol) forming acetals (primary carbons with two -OR groups and a hydrogen atom) and ketals (secondary carbons with two -OR groups) which do not react with LiAlH4; after desired step is complete, can be reverted back via step called deprotection (H2O cat. H+)

Question 16

are phenols acidic or basic

Answer 16

acidic because oxygen-containing anion is resonance-stabilizing by the ring

Question 17

quinone

Answer 17

results from treating phenols with oxidizing agents; makeup is 2,5 cyclohexadiene-1,4-dione; to name a molecule, add quinone to name of parent phenol; resonance stabilized electrophiles; not necessarily aromatic; serve as electron acceptors in ETC in both photosynthesis and aerobic respiration

Question 18

phylloquinone

Answer 18

vitamin K1

Question 19

menaquinones

Answer 19

class of molecules of vitamin K2

Question 20

hydroxyquinones

Answer 20

share same ring and carbonyl backbone as quinones but differ by the addition of one or more hydroxyl groups; have electron donating groups making them slightly less electrophilic than quinones (although still very reactive); naming: position of hydroxyl groups is indicated by a number, and total number of hydroxyl groups is indicated by a prefix with the substituent name hydroxy-

Question 21

ubiquinone

Answer 21

biologically active quinone; also called coenzyme Q; vital electron carrier associated with complexes I, II, and II of the ETC. also can be reduced to ubiquinol - this capacity allows it to be an electron carrier within the phospholipid bilayer