Nucleophiles have regions of electron _______, while electrophiles have regions of

electron _______.

a) excess; deficiency

b) deficiency; excess

c) excess; neutrality

d) neutrality; deficiency

The SN1 reaction proceeds via a ________ intermediate.

a) primary

b) secondary

c) neutral

d) carbocation

Which type of substrate will be the most likely candidate for an SN1 reaction?

a) primary

b) secondary

c) tertiary

d) any of the above

c) tertiary

Which type of substrate will be the most likely candidate for an SN1 reaction?

a) primary

b) secondary

c) tertiary

d) any of the above

A typical SN1 _______ will be a ______ base.

a) nucleophile; weak

b) nucleophile; strong

c) electrophile; weak

d) electrophile; strong

 The E in E2 stands for:

a) extramolecular

b) elimination

c) entropically favorable

d) elementary

The proton extracted in an E2 reaction must be ________ to the leaving group.

a) alpha

b) beta

c) gamma

d) delta

E2 reactions can produce:

a) alcohols

b) amines

c) alkanes

d) alkenes

E1 reactions can occur with a ________ substrate and a ________ base.

a) primary; strong
b) primary; weak

c) tertiary; strong

d) tertiary; weak

 In E1, the _____ step is the ______ step, which makes it the rate-determining step.

a) first; slow

b) first; fast

c) second; slow

d) second; fast

E1 proceeds via a:

a) bimolecular transition state

b) unimolecular intermediate

c) an acid-base reaction

d) both B and C

e) both A and C

 In the first step of E1:

a) the base extracts a proton

b) the leaving group leaves

c) the pi bond forms

d) the conjugate acid forms

 When dealing with a tertiary substrate and a strong base, _____ is most likely to

occur.

a) SN1

b) SN2

c) E1

d) E2

Tert-butoxide will tend to promote which reaction?

a) SN1

b) SN2

c) E1

d) E2

When the substrate is primary, which mechanisms are unlikely?

  a) SN1 and SN2

b) E1 and E2

c) SN1 and E1

d) SN2 and E2

When the base is extremely sterically hindered, which mechanisms are unlikely?

a) SN1 and SN2

b) E1 and E2

c) SN1 and E1

d) SN2 and E2

Which substance is capable of acting as either a base or a nucleophile?

a)hydroxide

b) tert-butoxide

c) propane

d) any of the above

If the base is weak, and the temperature is low, which mechanism is most likely?

a) SN1

b) SN2

c) E1

d) E2

If the base is strong, and the temperature is high, which mechanism is most

likely?

a) SN1

b) SN2

c) E1

d) E2

State the mechanism that will occur and draw the correct

product

[image]

SN2

[image]

State the mechanism that will occur and draw the correct product:

[image]+ t-BuOH

In order for E2 to occur, the proton being extracted and the leaving group must

be:

a) staggered

b) gauche

c) anti

d) any of the above

When doing E2 on a cyclohexane derivative, the proton being extracted and the

leaving group must both be in an ______ position.

a) axial

b) equatorial

c) cis

d) none of the above

a) axial

[image]

The particular configuration of base and proton is required for ______ orbital

overlap to occur and thereby the ______ bond to form.

a) sigma; pi

b) p; pi

c) s; sigma

d) pi; sigma

 We typically don’t discuss conformations for E2 on linear systems because ______

bonds rotate freely.

a) pi

b) double

c) triple

d) sigma

Carbocation rearrangement always ______ the stability and ________ the degree of

substitution on a carbocation intermediate.

a) increases; increases

b) increases; decreases

c) decreases; increases

d) decreases; decreases

Which is NOT a type of carbocation rearrangement?

a) hydride shift

b) methanide shift

c) alkanide shift

d) none of the above

3) When a secondary carbocation is adjacent to a _______ carbon, a ______ shift will

occur.

a) tertiary; methanide

b) tertiary; hydride

c) quaternary; hydride

c) none of the above

Carbocation rearrangement can occur during:

a) SN1

b) SN2

c) E1

d) both A and C

 A _____ hindered base will tend to produce the _______ product.

a) less; Hofmann

b) less; Zaitsev

b) more; Zaitsev

d) depends on the scenario

Which base is most likely to produce the Hofmann product?

a) hydroxide

b) methoxide

c) ethoxide

d) tert-butoxide

The Zaitsev product is the _____ substituted and thus the _____ energetically

favorable of the possible elimination products.

a) more; more

'b) more; less

c) less; more

d) less; less

What determines whether the Zaitsev or Hofmann product dominates?

a) degree of substitution on substrate

b) temperature

c) steric hindrance on base

d) none of the above

'The product that sits the lowest on an energy diagram is the ______ product, while

the pathway with the lowest activation energy yields the ________ product.

a) thermodynamic; kinetic

b) kinetic; thermodynamic

c) thermodynamic; dominant

d) kinetic; dominant

Higher temperatures favor the __________ product.

a) more substituted

b) less substituted

c) thermodynamic

d) kinetic