ch 2 HW

An alkyne with the molecular formula C4H6 was reduced with sodium (Na) in liquid ammonia (NH3). Ozonolysis of the resulting alkene afforded only one aldehyde product. What is the IUPAC name of the alkene that was formed by reduction of the starting alkyne?

(E)-but-2-ene

oxidation state of carbon in methanol

-2

oxidation state of c in methane

-4

in IUPAC nomenclature, what suffix indicates that the compound is an alcohol

-ol

oxidation state of C1 in butanol

0

the reduction of 1-hexyne with H2 and the Lindlar's catalyst affords

1-hexene

the pKa of an alcohol is generally around what range

16-18

reduction of 1-decyne to decane requires how many equivalents of hydrogen gas

2

which of the following is the strongest acid? 2,2,2-trichloroethanol 2,2-dichloroethanol ethanol 2-chloroethanol

2,2,2-trichloroethanol

which of the following is the strongest acid? 2,3-dichlorophenol 2,3,6-trichlorophenol 2-chlorophenol phenol

2,3,6-trichlorophenol

oxidation state of c in CO2

4

the conversion of NADH to NAD+ is often coupled with the conversion of

ADP to ATP

all else being equal, which of the following would be the strongest base? N anion C anion fluoride O anion

C anion

which of the following compounds is the strongest bronsted acid CH2BrCO2H CH2ICO2H

CH2BrCO2H

during metabolism, our bodies utilize a series of chemical reactions to break down large organic molecules into

CO2

identify the major mechanistic pathway when 1-methyl-bromocyclopentane is treated with sodium methoxide

E2

T/F NAD+ is an example of a biological reducing agent

F

T/F much like any other alcohol, phenol is able to be oxidized to a ketone by PCC

F

T/F tertiary alcohols can be oxidized by chromic acid (H2CrO4), but not by PCC

F

identify reagents that can be used to reduce an alkyne to the corresponding alkane

H2, Pt/Pd

which of the following cofactors, in the presence of the appropriate enzyme, serves as a hydride delivery agent

NADH

tertiary alcohols will undergo an ____ reaction when treated with a hydrogen halide like HBr

SN1

primary and secondary alcohols will undergo an ___ reaction when treated with either SOCl2 or PBr3

SN2

T/F a nucleophile is an electron-rich species which contains either alone pair of electrons or a pi bond

T

T/F an electrophile is an electron-poor species which bears a positive or partial positive charge

T

T/F polarizability is the ability of an atom to redistribute its electrons when affected by an outside influence

T

when phenol is prepared industrially in a process that involves the formation and oxidation of cumene, what industrially important by-product is fromed

acetone

in a dissolving metal reduction of an alkyne which of the following is false

all mechanistic steps involve the transfer of pairs of elcetrons

phenol is a precursor for the synthesis of which of the following commercially useful compounds

antioxidant food additives (BHT and BHA)

what is the commercial use of butylated hydroxytoluene (BHT)

antioxidant food-additive

DBU functions as a

base only

A Grignard reagent functions as a

carbanion

when cyclohexene is exposed to OsO4 and NMO, the name (including cis/trans stereochemistry) of the resulting product is

cis-cyclohexane-1,2-diol

phenol is prepared industrially via a multistep process involving the formation and oxidation of

cumene

identify the reagent(s) below that can be used to convert 1-methylcyclohexene into 1-methylcyclohexanol

dilute H2SO4

identify the major product that is obtained when 1-hexyne is treated with H2 and Pd

hexane

lithium aluminum hydride is an effective reducing agent because it delivers what species

hydride

1-fluoro-2-propanol is more acidic than 2-propanol due to _____ effects

inductive

2,2,2-trichloroethanol is more acidic than ethanol due to ____ effects

inductive

the generate a grignard reagent, one exposes an alkyl or aryl halide to what metal

magnesium

which is a stronger base? phenoxide or methoxide

methoxide

is the conversion of cyclohexanol to cyclohexene an oxidation, reduction, or neither

neither

in a SN2 substitution rxn, when can a rearrangement step occur

never

which statement is true

only the rate of an SN2 reaction (not the rate of SN1 reaction) is dependent on the concentration of the nucleophile

the grignard reaction is based on the chemistry of what type of species

organomagnesium compounds

in the industrial preparation of phenol, the conversion of benzene to phenol is considered an

oxidation

the industrial preparation of phenol involves the ___ of cumene to form cumene hydroperoxide

oxidation

in the industrial preparation of phenol from benzene, oxygen (O2) acts as a(n):

oxidizing agent

conjugate acid of phenoxide ion is called

phenol

the common name of hydrooxybenzene is ___, and it is used as a key precursor to many plastics and pharmaceuticals

phenol

which of the following is the most basic water methanol t-butyl alcohol potassium t-butoxide

potassium t-butoxide

alkene to alkane is a oxidation or reduction

reduction

is the conversion of cyclohexene to cyclohexane an oxidation, reduction, or neither?

reduction

phenol is more acidic than cyclohexanol due primarily to _____ effects

resonance

polarizability is directly related to the ____ of an atom

size

identify the major mechanistic pathway when 1-chloropentane is treated with KCN

sn2

identify the major mechanistic pathway when 1-chloropentane is treated with sodium ethoxide

sn2

when treated with osmium tetraoxide and NMO, an alkene will undergo a(n)

syn-dihydroxylation reaction

which of the following substrates undergo substitution ONLY through a SN1 mechanism?

tertiary substrate

consider the compound drawn. which of the following would be considered a nucleophilic site? pent-3-enol

the oxygen atom

regardless of the strength or size of the base used, benzyl bromide ALWAYS does substitution in preference to elimination. why?

there are no beta-hydrogens to eliminate

when cyclohexene is exposed to peroxyacid, followed by aqueous acid, the name (including cis/trans stereochemistry) of the resulting product is

trans-1,2-cyclohexanediol

identify the major product that is obtained when 2-hexyne is treated with sodium (Na) in liquid ammonia (NH3)

trans-2-hexene

grignard reagents CANNOT be prepared in which of the following solvents

water

why does water stop a Grignard reaction

water protonates the grignard reagent

ethanol (CH3CH2OH) functions as a

weak nu and weak base