Exam 1 - Alcohols

Question 1

___, ___, and ___ alcohols can react with sulfonate esters + base.

Answer 1

primary, secondary, and tertiary

Question 2

The larger the alcohol, the ___ acidic.

Answer 2

less

Question 3

___ can need heat.

Answer 3

E1

Question 4

Alcohols reacting with sulfonate esters lead to ___ of stereochemistry in the final product.

Answer 4

retention

Question 5

Alcohols reacting with PBr3 lead to ___ of stereochemistry in the final product.

Answer 5

inversion

Question 6

___, ___, and ___ alcohols can react with sulfonate esters.

Answer 6

primary, secondary, tertiary

Question 7

You can react an alcohol directly with a ___, in order to create an alkoxide.

Answer 7

metal (M = Li, Na, K)

Question 8

Primary branched alcohols reacting with strong acids can lead to ___ ___.

Answer 8

carbocation rearrangements

Question 9

SN2/E2 are faster in ___ ___ solvents.

Answer 9

polar aprotic (polar no OH)

Question 10

The mechanism of alcohols reacting with sulfonate esters also requires ___ in order to deprotonate the LG.

Answer 10

NEt3 (a base)

Question 11

Two examples of bases used in alcohol reactions:

Answer 11

NEt3 and pyridine

Question 12

An alcohol reacting with H2SO4 will produce a(n) ___ via an ___ mechanism.

Answer 12

alkene, elimination

Question 13

An alcohol is a ___ attached to a ___ carbon.

Answer 13

-OH, sp3

Question 14

E2 needs a ___/___ base.

Answer 14

strong/bulky base

Question 15

___/___ are faster in polar protic solvents.

Answer 15

SN1/E1

Question 16

___ and ___ alcohols can react with SOCl2/SOBr2 + base.

Answer 16

primary, secondary

Question 17

Alcohols reacting with SOCl2 and NEt3 lead to ___ of stereochemistry in the final product.

Answer 17

inversion

Question 18

Bigger alcohols are less acidic, because it is harder to stabilize the ___ ___.

Answer 18

conjugate base

Question 19

___, ___, and ___ alcohols can react with H2SO4.

Answer 19

primary, secondary, tertiary

Question 20

The ___ the alcohol, the less acidic.

Answer 20

larger

Question 21

Usually the more substituted alkene is favored (___ Rule).

Answer 21

Zaitsev’s Rule

Question 22

Remember: ___ ___ can happen in SN1 and E1 reactions!

Answer 22

carbocation rearrangements

Question 23

___ = Deprotonated alcohol.

Answer 23

alkoxide

Question 24

In alcohols reacting with strong acids (HBr, HI, HCl): ___ reacts faster than ___ which reacts faster than ___.

Answer 24

tertiary, secondary, primary

Question 25

An alcohol can react with ___ to produce an alkene via elimination.

Answer 25

H2SO4

Question 26

A base needs to be ___ orders of magnitude higher in order to deprotonate the alcohol.

Answer 26

3

Question 27

Only ___ and ___ alcohols can react with SOCl2 and NEt3.

Answer 27

primary, secondary

Question 28

SN2 mechanism leads to ___.

Answer 28

inversion

Question 29

You can react an alcohol with a ___ ___ in order to deprotonate the alcohol.

Answer 29

strong base (i.e. NaH)

Question 30

Alcohols can react with PBr3 in order to produce a ___ of the OH with a ___ group.

Answer 30

substitution, Br group

Question 31

Alcohols reacting with strong acids (HBr, HCl, HI) are good for ___ and ___ alcohols.

Answer 31

tertiary, primary (unbranched)

Question 32

Remember: In all chemistry, ___ chemistry always happens first! (It is the fastest). I.e.: Look out for ___ or ___.

Answer 32

acid-base chemistry, protonation, deprotonation

Question 33

Alcohols can react with SOCl2 and NEt3 (base) to produce a ___ of the OH with a ___ group.

Answer 33

substitution, Cl group

Question 34

___ needs a strong/bulky base.

Answer 34

E2

Question 35

vicinal diol - OHs attached to ___ ___.

Answer 35

adjacent Cs

Question 36

SN1/E1 are faster in ___ ___ solvents.

Answer 36

polar protic (polar w/ OH)

Question 37

Only ___ and ___ alcohols can react with PBr3.

Answer 37

primary, secondary

Question 38

Remember: ___ are formed in SN1 and E1 reactions!

Answer 38

carbocations

Question 39

A secondary alcohol reacting with PBr3 will go through a ___ mechanism.

Answer 39

SN2

Question 40

___ ___ - OHs attached to adjacent Cs.

Answer 40

vicinal diol

Question 41

A primary alcohol reacting with a strong acid (HBr, HCl, HI) goes through a ___ mechanism.

Answer 41

SN2

Question 42

Vicinal diols reacting with H2SO4 have a ___ ___ in their mechanism which leads to their unique final product.

Answer 42

carbocation rearrangemnet

Question 43

Carbocation group shifting, in order from fastest to slowest: ___ > ___ > ___ ___ > ___

Answer 43

tertbutyl > isopropyl > primary alkyl > methyl

Question 44

The product of alcohols reacting with sulfonate esters is -OH becoming ___.

Answer 44

-OTS

Question 45

E1 can need ___.

Answer 45

heat

Question 46

The mechanism of alcohols reacting with SOCl2 and NEt3 requires a ___ to deprotonate the LG before it leaves.

Answer 46

base

Question 47

___/___ are faster in polar aprotic solvents.

Answer 47

SN2/E2

Question 48

___ and ___ alcohols can react with PBr3.

Answer 48

primary, secondary

Question 49

___ and ___ alcohols can react with strong acid (i.e. HI, HBr, HCl).

Answer 49

primary (unbranched), tertiary

Question 50

Alcohols can react with sulfonate esters to create one ___ ___ ___.

Answer 50

large good LG

Question 51

A secondary alcohol reacting with a strong acid (HBr, HCl, HI) goes through a ___ mechanism.

Answer 51

SN1

Question 52

SN1/E1 are faster in polar protic (polar w/ OH) solvents, because the OH helps stabilize the ___.

Answer 52

carbocation.

Question 53

Examples of sulfonate esters reacting with Alcohol (along with a base of course):

Answer 53

TsCl, MsCl, Tf2O

Question 54

The mechanism for an alcohol reacting with PBr3 is like ___ ___ reactions.

Answer 54

two SN2

Question 55

Usually the ___ substituted alkene is favored (Zaitsev’s Rule).

Answer 55

more

Question 56

A tertiary alcohol reacting with a strong acid (HBr, HCl, HI) goes through a ___ mechanism.

Answer 56

SN1

Question 57

In sulfonate ester reactions with alcohols, the ___ is still in the final product (NOT kicked out!)

Answer 57

oxygen (O)

Question 58

Primary alcohols reacting with H2SO4 will go through a ___ mechanism. Secondary and Tertiary alcohols reacting with H2SO4 will go through a ___ mechanism.

Answer 58

E2, E1

Question 59

___ alcohols reacting with H2SO4 will go through a E2 mechanism. ___ and ___ alcohols reacting with H2SO4 will go through a E1 mechanism.

Answer 59

Primary, Secondary and Tertiary

Question 60

You can react an alcohol with a ___ ___ to make it a good leaving group

Answer 60

strong acid (i.e. HBr)

Question 61

___ mechanism leads to inversion.

Answer 61

SN2