Quiz | Hydroxy Functional Group - Alcohols

1

What is the property of an alcohol?

Soluble in water

Polar

Amphoteric

All of the above

2

What type of alcohol is 2,3-dimethylbutan-2-ol?

Primary alcohol

Secondary alcohol

Tertiary alcohol

Quaternary alcohol

The hydroxy function of 2,3-dimethylbutan-2-ol is on a carbon attached to THREE other carbon atoms ⇒ tertiary alcohol

3

What is the best method to selectivity synthesize butan-1-ol?

CH3COONa and then NaOH/H2O

NaOH

EtOH and LiBr

tBuOH and then KOH

Alcohols can be synthesized by SN reactions from haloalkanes. To avoid competition between SN and E reactions, the halogen atom must be replaced by a better leaving group:

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4

Which of the following will convert butan-2-ol to a ketone?

O3 and Zn

LiAlH4

NaBH4

PCC (Pyridinium Chlorochromate)

​​​​Carbonyls are formed by oxidation of alcohols using Na2Cr2O7 or PCC

5

Which of the following reagents is best for conerting propanal to alcohol?

PCC (Pyridinium Chlorochromate)

NaBH4

LiAlH4

Na2Cr2O7, H2SO4, H2O

Alcohols can be synthesized by reduction of carbonyls using H- donors (NaBH4 or LiAlH4). LiAlH4 is by far the more reactive of the 2 compounds ⇒ NaBH4 is generally preferred for the oxydation of primary alcohol to avoid any degradation of the compound

6

Which of the following will convert 2-methylpropan-1-ol to a carboxylic acid?

PCC (Pyridinium Chlorochromate)

NaBH4

LiAlH4

Na2Cr2O7, H2SO4, H2O

A carboxylic acid can be formed by overoxydation of a primary alcohol using Na2Cr2O7, H2SO4, H2O

7

Which of the following will convert butan-2-one to 3-methylpentan-3-ol?

EtMgBr and then H2O

MeLi and then H2O

(CH3)2CuLi and then H2O

None of the above

Butan-2-one to 3-methylpentan-3-ol: alcohol synthesis + formation of a Carbon-Carbon bond ⇒ organometallic R-M is used
The added alkyl chain is CH3CH2 (ethyl chain) ⇒ the only possible available conditions are EtMgBr and then H2O

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8

Which of the following will convert bromoethane into pentane?

CH3CH2CH2MgBr

CH3CH2CH2Li

(CH3CH2CH2)2CuLi

All the above

Bromoethane into pentane: carbon-carbon coupling reactions ⇒ it only works with Gilman reagent