Organic Chem Exam 3 - Ganley Mizzou

a) nucleophile

a) nucleophile

alkyl halides undergo a substitution when reacted with a…

a) nucleophile

b) base

b) base

alkyl halides undergo an elimination reaction when reacted with a…

a) nucleophile

b) base

a) concerted substitution

SN2 reaction is a ___________ ___________ reaction

a) concerted substitution

b) stepwise substitution

c) concerted elimination

d) stepwise elimination

c) concerted elimination

E2 reaction is a _____________ ___________ reaction

a) concerted substitution

b) stepwise substitution

c) concerted elimination

d) stepwise elimination

b) stepwise substitution

SN1 reaction is a __________ __________ reaction

a) concerted substitution

b) stepwise substitution

c) concerted elimination

d) stepwise elimination

d) stepwise elimination

E1 reaction is a ___________ __________ reaction

a) concerted substitution

b) stepwise substitution

c) concerted elimination

d) stepwise elimination

loss of a leaving group

nucleophilic attack

what are the two steps to an SN2 reaction

SN2

which reaction causes inversion of configuration

b) strong nucleophile

an SN2 reaction needs a:

a) strong base

b) strong nucleophile

c) weak base

d) weak nucleophile

a) strong base

an E2 reaction needs a:

a) strong base

b) strong nucleophile

c) weak base

d) weak nucleophile

I-, Br-, Cl-, HS-, RS-, HO-, RO-, NC-

what are 8 strong nucleophiles

negative charge, big atom, less EN

what are three characteristics of a strong nucleophile

H2O, ROH

what are 2 weak nucleophiles

neutral, small atom

what are 2 characteristics of a weak nucleophile

H bonding in protic

what is the difference between protic and aprotic solvents

H20, CH3OH (methanol), CH3CH2OH(ethanol), NH3(ammonia), CH3COOH(acetic acid)

what are 5 protic solvents

CH3COCH3 (acetone), DMSO, DMF, HMPA, CH3CN (acetonitrile)

what are 5 polar aprotic solvents

a) polar protic

what kind of solvent does SN1 reactions favor?

a) polar protic

b) polar aprotic

b) polar aprotic

what kind of solvent does SN2 reactions favor?

proton transfer, loss of a leaving group

what are the two steps of an E2 reaction?

alkenes

what are formed by elimination reactions

b) trans

what is more stable in alkenes:

a) cis

b) trans

c) both are equally stable

regioselective

when something is not switching sides during an addition reaction:

stereospecific

when only one kind of isomer is present (cis v. trans)

more

more substituted = _____ stable

b) hofmann

the elimination product in which the double bond is in the least substituted region:

a) zaitsev

b) hofmann

a) zaitsev

the elimination product in which the double bond is in the most substituted region:

a) zaitsev

b) hofmann

bulky base

what causes a selection for hofmann product

180 degrees

how far apart should the pieces involved in an elimination reaction be

c) major and minor

in a stereoselective elimination, you will get … products

a) major only

b) minor only

c) major and minor

a) major only

in stereospecific eliminations you will get … products

a) major only

b) minor only

c) major and minor

axial

in halocyclohexanes, E2 can only occur when halogen is _______.

loss of a leaving group, nucleophilic attack, proton transfer

what are the three steps to an SN1 reaction

b) stepwise reaction

a carbocation is formed in a …

a) concerted reaction

b) stepwise reaction

c) both

loss of a leaving group, proton transfer

what are the two steps to an E1 reaction

f) C and D

which reactions have the potential to go through a carbocation rearrangement?

a) SN2

b) E2

c) SN1

d) E1

e) A and B

f) C and D

a) regioselective

E1 reactions are

a) regioselective

b) regiospecific

a) stereoselective

E1 reactions are

a) stereoselective

b) stereospecific

a) stereoselective

SN1 reactions are

a) stereoselective

b) stereospecific

b) E2

if you have a strong base, weak nucleophile, what reaction(s) are able to occur

a) SN2

b) E2

c) SN1

d) E1

e) a and b

f) a and c

g) c and d

e) a and b

if you have a strong base, strong nucleophile, what reaction(s) are able to occur

a) SN2

b) E2

c) SN1

d) E1

e) a and b

f) a and c

g) c and d

f) a and c

if you have a weak base, strong nucleophile, what reaction(s) are able to occur

a) SN2

b) E2

c) SN1

d) E1

e) a and b

f) a and c

g) c and d

g) c and d

if you have a weak base, weak nucleophile, what reaction(s) are able to occur

a) SN2

b) E2

c) SN1

d) E1

e) a and b

f) a and c

g) c and d

DBN, DBU

what are examples of strong base weak nucleophiles

HO-, MeO-, EtO-

what are examples of strong base strong nucleophiles

I-, Br-, Cl-, RS-, HS-, RSH, H2S

what are examples of weak base strong nucleophiles

H2O, MeOH, EtOH

what are examples of weak base weak nucleophiles

E2

if you have a primary substrate and a strong base weak nucleophile, what reaction(s) are occuring

E2

if you have a secondary substrate and a strong base weak nucleophile, what reaction(s) are occuring

E2

if you have a tertiary substrate and a strong base weak nucleophile, what reaction(s) are occuring

Major: SN2

Minor: E2

if you have a primary substrate and a strong base strong nucleophile, what reaction(s) are occuring

Major: E2

Minor: SN2

if you have a secondary substrate and a strong base strong nucleophile, what reaction(s) are occuring

E2

if you have a tertiary substrate and a strong base strong nucleophile, what reaction(s) are occurring

SN2

if you have a primary substrate and a weak base strong nucleophile, what reaction(s) are occurring

SN2

if you have a secondary substrate and a weak base strong nucleophile, what reaction(s) are occurring

SN1

if you have a tertiary substrate and a weak base strong nucleophile, what reaction(s) are occurring

none

if you have a primary substrate and a weak base weak nucleophile, what reaction(s) are occurring

none

if you have a secondary substrate and a weak base weak nucleophile, what reaction(s) are occurring

equal: SN1 and E1

if you have a tertiary substrate and a weak base weak nucleophile, what reaction(s) are occurring

b) stereospecific

SN2 reactions are

a)stereoselective

b)stereospecific

a) stereoselective

E2 reactions are

a) stereoselective

b) stereospecific

a) regioselective

E2 reactions are

a) regioselective

b) regiospecific

OMs, OTs, OTf

what are the 3 “excellent” leaving groups: alkyl sulfonates

HX

what is added in hydrohalogenation

b) anti-markovnikov

what kind of addition does hydrohalogenation do when it is conducted with ROOR (peroxide)

a) markovnikov

b) anti-markovnikov

a) markovnikov

what kind of addition does hydrohalogenation do when it isn’t conducted with ROOR (peroxide)

a) markovnikov

b) anti-markovnikov

yes

is there a potential for carbocation rearrangement in hydrohalogenation

if you have chiral centers

when will you have both enantiomers for a hydrohalogenation and acid catalyzed hydration

hydrohalogenation

what addition reaction is going to take place if your solvents are: HX or HX, ROOR

acid catalyzed hydration

what addition reaction is going to take place if your solvents are: H2SO4 and H2O

H, OH

what is being added to the alkene in an acid catalyzed hydration

a) markovnikov

what kind of addition does acid catalyzed hydration do

a) markovnikov

b) anti-markovnikov

yes

does acid catalyzed hydration have the potential for a carbocation rearrangement

oxymercuration demurcuration

what kind of addition reaction is taking place if you reactants are; Hg(OAc)2H20 and NaBH4

H, OH

what is added to the alkene in an oxymercuration demurcuration reaction

a) markovnikov

what kind of addition does oxymercuration demurcuration do

a) markovnikov

b) anti-markovnikov

hydroboration oxidation

what kind of addition reaction is taking place if your solvents are BH3, THF, H2O2, NaOH

H, OH

what is added to the alkene in a hydroboration oxidation

b) anti-markovnikov

what kind of addition does hydroboration oxidation do

a) markovnikov

b) anti-markovnikov

a) syn

what kind of addition does hydroboration oxidation do

a) syn

b) anti

catalytic hydrogenation

what kind of addition reaction is taking place if your solvents are H2, Pt

if it’s mesos

when will you not get enantiomers when doing a catalytic hydrogenation or halogenation

H2

what is added to the alkene in a catalytic hydrogenation

a) syn

what kind of addition does catalytic hydrogenation do

a) syn

b) anti

halogenation

what kind of addition reaction is taking place when your solvent is X2

X2

what is added to the alkene in a halogenation reaction

b) anti

what kind of addition does halogenation do

a) syn

b) anti

halohydrin

what kind of addition reaction is taking place if your solvents are X2 and H2O

OH, X

what is added to the alkene in a halohydrin reaction

b) anti

what kind of addition does halohydrin do

a) syn

b) anti

halogen

in halohydrin, the _______ acts as a hydrogen would in a markovnikov addition

anti dihydroxylation

what kind of addition reaction is taking place if your solvents are RCO2H (peroxy acid → MCPBA) and H3O+

(OH)2

what is added to the alkene in an anti dihydroxylation

b) anti

what kind of addition does an anti dihydroxylation do

a) syn

b) anti

trans diol

what is the product of anti dihydroxylation

epoxide (2 C bond to same O)

what is an intermediate of antidihydroxylation

syn dihydroxylation

what kind of addition reaction is taking place if your solvents are KMnO4, NaOH, and cold

syn dihydroxylation

what kind of addition reaction is taking place if your solvents are OsO4, NaHSO3, and H2O

(OH)2

what is added to the alkene in a syn dihydroxylation

a) syn

what kind of addition does syn dihydroxylation do

a) syn

b) anti