4) What type of orbital do the lone pair electrons on oxygen occupy in ethanol?
A) ?
B) ?
C) p
D) sp
E) sp3
E) sp3
5) What two atomic orbitals or hybrid atomic orbitals overlap to form the C-O bond in ethanol?
A) C sp2 + O sp2
B) C sp3 + O sp3
C) C sp2 + O sp3
D) C sp3 + O sp2
E) none of the above
B) C sp3 + O sp3
13) 2-Methylbutan-1-ol is classified as __________.
A) a primary alcohol
B) a secondary alcohol
C) a tertiary alcohol
D) a phenol
E) an enol
A) a primary alcohol
14) 1-Methylcyclopentan-1-ol is classified as __________.
A) a primary alcohol
B) a secondary alcohol
C) a tertiary alcohol
D) a phenol
E) an enol
C) a tertiary alcohol
15) 2-Methylpentan-3-ol is classified as __________.
A) a primary alcohol
B) a secondary alcohol
C) a tertiary alcohol
D) a phenol
E) an enol
B) a secondary alcohol
60) Which of the following alkyl halides would be suitable to use when forming a Grignard reagent?
A) BrCH2CH2CH2CN
B) CH3COCH2CH2Br
C) (CH3)2NCH2CH2Br
D) H2NCH2CH2Br
E) all of the above
C) (CH3)2NCH2CH2Br
65) Which of the compounds below has a pKa that most closely matches the pKa of ethanol?
A) water
B) ammonia
C) acetic acid
D) phenol
E) HCl
A) water
67) Which of the following reagents or sequences do not produce an alcohol or diol from an alkene starting material?
A) H+, H2O
B) HCO3H
C) BH3.THF followed by H2O2, NaOH
D) Hg(OAc)2, H2O followed by NaBH4
E) OsO4, H2O2
B) HCO3H
68) Which of the following terms best describes the reactive nature of a Grignard reagent?
A) carbocation
B) free radical
C) electrophile
D) nucleophile
E) carbene
D) nucleophile
70) When a ketone is treated with LiAlH4 followed by addition of H2O, what general class of product results?
A) primary alcohol
B) secondary alcohol
C) tertiary alcohol
D) ether
E) aldehyde
B) secondary alcohol
71) When an aldehyde is treated with LiAlH4 followed by addition of H2O, what general class of product results?
A) primary alcohol
B) secondary alcohol
C) tertiary alcohol
D) ether
E) ketone
A) primary alcohol
90) Reaction of ethylmagnesium bromide with which of the following compounds yields a tertiary alcohol after quenching with aqueous acid?
A) H2CO
B) CH3CHO
C) (CH3)2CO
D) ethylene oxide
E) n-butyllithium
C) (CH3)2CO
91) Reaction of ethylmagnesium bromide with which of the following compounds yields a secondary alcohol after quenching with aqueous acid?
A) H2CO
B) CH3CHO
C) (CH3)2CO
D) ethylene oxide
E) n-butyllithium
B) CH3CHO
92) Reaction of ethylmagnesium bromide with which of the following compounds yields a primary alcohol after quenching with aqueous acid?
A) ethyl acetate
B) CH3CHO
C) (CH3)2CO
D) ethylene oxide
E) n-butyllithium
D) ethylene oxide
A)
B)
C)
D)
E) both A and D
Answer: E
...
95) Which of the following substrates will not form a Grignard reagent when treated with Mg/diethylether?
A)
B)
C)
D)
E)
Answer: B
...
97) Reduction of a ketone with NaBH4 will result in the formation of --
A) a primary alcohol
B) an alkene
C) a secondary alcohol
D) an alkane
E) an aldehyde
C) a secondary alcohol
98) Which series of reactions would best facilitate the following conversion?
A) 1. KMnO4 (aq)
2. Hg(OAc)2 (aq)
3. NaBH4/OH-
B) 1. NaBH4
2. H3PO4/?
C) 1. H3C-MgBr
2. H2O/H3O+
D) 1. NaBH4
2. HBr (g)
3. Mg/ether
4. H2O/H3O+
E) 1. Raney nickel
2. H3C-MgBr
3.
B) 1. NaBH4
2. H3PO4/?