__________, also known as wood alcohol, is used as a fuel and as a solvent. Ingestion of this alcohol can lead to blindness and death
Methanol or methyl alcohol
__________ is dissolved in water to make the solution sold commercially as rubbing alcohol.
Isopropyl alcohol or Propan-2-ol
__________, commonly used in automobile antifreezes, is a diol which is highly toxic if ingested.
Ethylene glycol
What type of orbital do the lone pair electrons on oxygen occupy in ethanol?
sp3
What two atomic orbitals or hybrid atomic orbitals overlap to form the C-O bond in ethanol?
C sp3 + O sp3
2-Methylbutan-1-ol is classified as __________.
a primary alcohol
1-Methylcyclopentan-1-ol is classified as __________.
a tertiary alcohol
2-Methylpentan-3-ol is classified as __________.
a secondary alcohol
Which of the following alkyl halides would be suitable to use when forming a Grignard reagent?
(CH3)2NCH2CH2Br
Which of the compounds below has a pKa that most closely matches the pKa of ethanol?
water
What gaseous byproduct is evolved when sodium metal is added to ethanol?
H2, molecular hydrogen
Which of the following reagents or sequences do not produce an alcohol or diol from an alkene starting material?
HCO3H
Which of the following terms best describes the reactive nature of a Grignard reagent?
nucleophile
When a ketone is treated with LiAlH4 followed by addition of H2O
what general class of product results?,secondary alcohol
When an aldehyde is treated with LiAlH4 followed by addition of H2O
what general class of product results?,primary alcohol
Arrange the following alcohols in order of increasing boiling point:
(CH3)3COH
CH3(CH2)4OH
(CH3)3CCH2OH
(CH3)2CHCH2CH2OH
(CH3)3COH < (CH3)3CCH2OH < (CH3)2CHCH2CH2OH < CH3(CH2)4OH
Reaction of ethylmagnesium bromide with which of the following compounds yields a tertiary alcohol after quenching with aqueous acid?
(CH3)2CO
Reaction of ethylmagnesium bromide with which of the following compounds yields a secondary alcohol after quenching with aqueous acid?
CH3CHO
Reaction of ethylmagnesium bromide with which of the following compounds yields a primary alcohol after quenching with aqueous acid?
ethylene oxide
Classify the reaction below as an oxidation a reduction, or neither.
(CH3)2CHCH2OH ? (CH3)2CHCHO
oxidation
Classify the reaction below as an oxidation, a reduction, or neither.
PhCO2H ? PhCH2OH
reduction
Classify the reaction below as an oxidation, a reduction, or neither.
cis-pent-2-ene ? pentane
reduction
) In the chromic acid oxidation of alcohols, the chromium is
reduced from Cr+6 to Cr+3
The Williamson ether synthesis proceeds via an __________ mechanism
SN2
The enzyme, alcohol dehydrogenase, which is produced by the liver, converts ethanol to __________, a normal body metabolite
acetic acid
Which of the following reagents can be used to convert cyclopentanol to cyclopentane?
TsCl, pyridine followed by LiAlH4
H2SO4, heat followed by H2, Pt
) Which of the following alcohols will give a positive chromic acid test?
cyclohexanol
pentan-3-ol
When (R)-butan-2-ol is treated with TsCl in pyridine, the product formed is:
a single enantiomer.
Which of the following alcohols will react most rapidly with the Lucas reagent (HCl, ZnCl2)?
(CH3)3COH
) Which set of reagents will best convert 2,2-dimethylpropan-1-ol (neopentyl alcohol)
to 4,4-dimethylpentan-2-ol?
1. SOCl2
2. Mg
3. CH3CHO
4. H3O+
Which of the following alcohols undergoes dehydration upon heating with concentrated H2SO4 without carbocation rearrangement?
3-methylpentan-3-ol
The reaction of CH3CH2MgBr with CH3COCH2CH3 gives:
an achiral product.
Which of the following reagents is not typically viewed as an oxidizing agent?
KCl
Which of the following reagents is the best choice for oxidizing a primary alcohol to an aldehyde?
pyridinium chlorochromate
Which of the following catalysts is commonly used in industry to dehydrogenate alcohols?
CuO
What compound is produced when (R)-pentan-2-ol is treated with TsCl followed by NaI?
(S)-2-iodopentane
Through what basic mechanism is 1-methylcyclohexanol converted to 1-bromo-1-methylcyclohexane upon treatment with HBr?
SN1
What compound results when 1-butanol is treated with P/I2?
CH3CH2CH2CH2I
What class of organic compound is the major product of the acid catalyzed reaction of an alcohol with a carboxylic acid?
ester
Which of the following compounds has carbon in the highest oxidation state?
CO2
Which of the following oxidants will convert a primary alcohol to an aldehyde?
1) sodium dichromate /sulfuric acid
2) copper oxide
3) pyridinium chlorochromate
4) dimethylsulfoxide, oxalyl chloride
2,3,4
Which alcohol reacts most rapidly with the Lucas reagent?
benzyl alcohol
Identify the sequence of reactions that successfully completes the following transformation
1) BH3 2) H2O2 / NaOH 3) P, I2
1) HBr / h? 2) NaI, acetone
Which energetic material is a nitrate ester?
nitroglycerin