Reagents

Question 1

NaH

Answer 1

Very strong, H Will react with an alcohol to make R-O(-).

Question 2

Na

Answer 2

Will react with an alcohol to make R-O(-)

Question 3

NaBH4,MeOH

Answer 3

A reducing agent that Can be used to reduce ketones or aldehydes to alcohols.

Question 4

1) LiAlH4, 2) H3O+

Answer 4

A strong reducing agent that Can be used to reduce ketones, aldehydes, esters, or carboxylic acids to give an alcohol

Question 5

H2, Pt

Answer 5

Reducing agent. Generally used to reduce alkenes and/or alkynes to alkanes, but in some cases, it can also be used to reduce ketones and/or aldehydes to alcohols.

Question 6

Mg

Answer 6

Can be used to convert an organohalide (RX, where R = alkyl, aryl or vinyl group) into a Grignard reagent (RMgX).

Question 7

RMgX

Answer 7

A Grignard reagent. Very strong nucleophiles (and very strong bases as well), and react with aldehydes or ketones. Aldehydes are converted into secondary alcohols (except for formaldehyde which is converted to a primary alcohol), while ketones are converted to tertiary alcohols. Esters are converted to tertiary alcohols when treated with excess Grignard.

Question 8

TMSCl, Et3N

Answer 8

Trimethylsilyl chloride [(CH3)3SiCl], in the presence of a base (such as triethylamine), will protect an alcohol (ROH is converted to ROTMS).

Question 9

TBAF

Answer 9

Tetrabutylammonium fluoride. Used for deprotection of alcohols with silyl protecting groups (ROTMS is converted to ROH).

Question 10

HX

Answer 10

HBr and HCl are strong acids that also provide a source of a strong nucleophile. Can be used to convert an alcohol into an alkyl bromide or alkyl chloride.

Question 11

TsCl

Answer 11

Tosyl chloride (TsCl) will convert an alcohol into a tosylate. This is important because it converts a bad leaving group (HO−) into a good leaving group (TsO−).

Question 12

PBr3

Answer 12

Converts primary or 2ndary alcohol to alkyl bromide. If OH group is connected to a chiral center, we expect inversion (typical for an SN2 process).

Question 13

SOCl2, pyridine

Answer 13

Thionyl chloride (SOCl2) can be used to convert a primary or secondary alcohol into an alkyl chloride. If the OH group is connected to a chiral center, reaction conditions can be selected for inversion of configuration (typical for an SN2 process).

Question 14

HCl, ZnCl2

Answer 14

convert an alcohol into an alkyl chloride.

Question 15

Na2Cr2O7, H2SO4, H2O

Answer 15

strong oxidizing agent. Primary alcohols are oxidized to give carboxylic acids, while secondary alcohols turned into ketones. Tertiary alcohols are generally unreactive.

Question 16

PCC, CH2Cl2

Answer 16

Pyridinium chlorochromate (PCC) is a mild oxidizing agent that will oxidize a primary alcohol to give an aldehyde, rather than a carboxylic acid. Secondary alcohols are oxidized to give ketones. Methylene chloride (CH2Cl2) is a solvent.

Question 17

DMP, CH2Cl2

Answer 17

a mild oxidizing agent that turns alcohols into aldehydes or ketones

Question 18

1) DMSO, (COCl)2,
2) Et3N

Answer 18

Swern oxidation- oxidize a primary alcohol to an aldehyde, not a carboxylic acid. Secondary alcohols are oxidized to ketones.

Question 19

Ester

Question 20

Propyl

Answer 20

3

Question 21

Sp3 Carbon Plus HBr

Answer 21

Cleaves C-O bond, changes it to C-Br

Question 22

1. H2SO4
2. NaH
3. EtI

Answer 22

Adds Ethoxy to alkene

Question 23

1. Hg(OAc)2, EtOH
2. NaBH4

Answer 23

Adds Ethoxy to alkene

Question 24

MCPBA

Answer 24

Forms an epoxide

Question 25

MeO, H2SO4

Answer 25

Turns an epoxide into OH, OMe, plus enantiomer