Exam 1 - Ethers and Silyl Ethers

Question 1

If an unsymmetrical ether is treated with a strong acid (i.e. HI, HBr, HCl), choose the LG which produces a ___ ___ ___.

Answer 1

more stable carbocation

Question 2

A ___ ___ alcohol treated with H2SO4 and heat will produce an ether product via SN2.

Answer 2

primary unbranched alcohol

Question 3

Treating an alkene with ___ and ___ will produce a simple ether.

Answer 3

H2SO4, CH3OH

Question 4

In Acid Catalyzed Addition of alcohols to alkenes to create ethers (H2SO4 and CH3OH), the alcohol adds to the side with the ___ ___ ___.

Answer 4

more stable carbocation

Question 5

Silyl Ethers are the protecting groups for ___.

Answer 5

-OH

Question 6

-OTMS, -OTBDMS, all Silyl Ethers are removed with ___ in the last step.

Answer 6

TBAF

Question 7

In Acid Catalyzed Dehydration of alcohols (H2SO4 and heat), it only works with ___ ___ and can only make ___ ___.

Answer 7

primary alcohols, symmetric ethers

Question 8

A ___ ether treated with a strong acid (i.e. HI, HBr, HCl) will go through SN2.

Answer 8

primary

Question 9

An alkene reacting with H2SO4 needs ___ or a ___ ___ in order to do the reaction (produce an ether).

Answer 9

CH3OH, primary alcohol

Question 10

Williamson Ether Synthesis with a ___ or ___ alkyl group will instead produce an alkene via elimination.

Answer 10

secondary, tertiary

Question 11

___ ___ - Unreactive group that is reversibly created to prevent a functional group (like OH) from reacting and producing unwanted products.

Answer 11

Protecting groups

Question 12

Acid catalyzed dehydration of alcohols only works for creating ___ ___ from ___ ___ alcohols.

Answer 12

symmetrical ethers from primary unbranched alcohols

Question 13

A ___ or ___ alcohol treated with H2SO4 and heat will simply produce an alkene via EI.

Answer 13

secondary, tertiary

Question 14

One can also make ethers via acid catalyzed dehydration. In this rxn, you use ___ with ___.

Answer 14

H2SO4 with heat

Question 15

When treating an alkene with H2SO4 and CH3OH, a ___ is formed. The alcohol then adds to the ___ stable carbocation.

Answer 15

carbocation, more stable

Question 16

In ___ ___ ___, one can treat a primary, secondary, or tertiary alcohol with a strong base (i.e. NaH) to produce an ether.

Answer 16

Williamson Ether Synthesis

Question 17

Treating an alkene with H2SO4 and CH3OH will produce a simple ___.

Answer 17

ether

Question 18

In Williamson Ether Synthesis, one can treat a primary, secondary, or tertiary alcohol with a ___ ___ and ___ ___ to produce an ether.

Answer 18

strong base (i.e. NaH) and alkyl halide

Question 19

In Williamson Ether Synthesis, you will first make the ___, THEN the ether.

Answer 19

alkoxide

Question 20

A primary unbranched alcohol treated with H2SO4 and heat will produce a(n) ___ product via ___.

Answer 20

ether via SN2

Question 21

A secondary and tertiary ether treated with a strong acid (i.e. HI, HBr, HCl) will go through ___.

Answer 21

SN1

Question 22

A ___ and ___ ether treated with a strong acid (i.e. HI, HBr, HCl) will go through SN1.

Answer 22

secondary and tertiary

Question 23

Once TBDMSCl is added to the -OH, write it as:

Answer 23

-OTBDMS

Question 24

Williamson Ether Synthesis only works with ___ or a ___ ___.

Answer 24

CH3, primary LG

Question 25

___ ___ are the protecting groups for -OH.

Answer 25

Silyl Ethers

Question 26

A primary unbranched alcohol treated with ___ and ___ will produce an ether product via SN2.

Answer 26

H2SO4 and heat

Question 27

An ether can be treated with a ___ ___ to split it apart and create an alcohol and an alkyl halide.

Answer 27

strong acid (i.e. HI, HBr, HCl)

Question 28

A secondary or tertiary alcohol treated with H2SO4 and heat will simply produce a(n) ___ via ___.

Answer 28

alkene, EI

Question 29

In Williamson Ether Synthesis (strong base+ alkyl halide), the alkyl halide must be ___ or ___.

Answer 29

methyl or primary

Question 30

A primary ether treated with a strong acid (i.e. HI, HBr, HCl) will go through ___.

Answer 30

SN2

Question 31

In Williamson Ether Synthesis, one can treat a ___, ___, or ___ alcohol with a strong base (i.e. NaH) and alkyl halide to produce an ether.

Answer 31

primary, secondary, tertiary

Question 32

A secondary or tertiary alcohol treated with ___ and ___ will simply produce an alkene via E1.

Answer 32

H2SO4 and heat

Question 33

Best Silyl Protecting Groups to add to protect/hide -OH groups:

Answer 33

TMSCl, TBDMSCl

Question 34

Williamson Ether Synthesis with a secondary or tertiary alkyl group will instead produce a(n) ___ via ___.

Answer 34

alkene, elimination

Question 35

Once TMSCl is added to the -OH, write it as:

Answer 35

-OTMS