1 A Uhcl Orgo Ii Exam3.0 Questions Ch17/18

Front 1

1) What type of orbital do the lone pair electrons on oxygen occupy in ethanol?
A) σ
B) π
C) p
D) sp
E) sp3

Back 1

E) sp3

Front 2

2) 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

Back 2

B) C sp3 + O sp3

Front 3

3) 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

Back 3

A) a primary alcohol

Front 4

4) 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

Back 4

C) a tertiary alcohol

Front 5

5) 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

Back 5

B) a secondary alcohol

Front 6

7) Identify the statement that correctly describes methanol.
A) It is used in alcoholic beverages.
B) It can be used as a fuel source but releases less energy than gasoline when combusted.
C) It once was used as an anesthetic.
D) It is also referred to as rubbing alcohol.

Back 6

B) It can be used as a fuel source but releases less energy than gasoline when combusted.

Front 7

8) 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

Back 7

A) water

Front 8

9) 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

Back 8

B) HCO3H

Front 9

10) 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

Back 9

D) nucleophile

Front 10

11) 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

Back 10

C) (CH3)2CO

Front 11

12) 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

Back 11

B) CH3CHO

Front 12

13) 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

Back 12

D) ethylene oxide

Front 13

14) The reaction of CH3CH2MgBr with CH3COCH2CH3 gives:
A) an achiral product.
B) a mixture of diastereomers.
C) the racemate of a chiral product.
D) a single enantiomer.
E) none of the above

Back 13

A) an achiral product.

Front 14

15) 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

Back 14

C) (CH3)2NCH2CH2Br

Front 15

17) 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

Back 15

B) secondary alcohol

Front 16

18) 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

Back 16

A) primary alcohol

Front 17

19) 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

Back 17

C) a secondary alcohol

Front 18

22) The acidity of a thiol proton most closely resembles which of the following acids?
A) phenol
B) ethanol
C) acetic acid
D) ammonia

Back 18

A) phenol

Front 19

23) Classify the reaction below as an oxidation, a reduction, or neither.
(CH3)2CHCH2OH → (CH3)2CHCHO
A) oxidation
B) reduction
C) neither

Back 19

A) oxidation

Front 20

24) Classify the reaction below as an oxidation, a reduction, or neither.
PhCO2H → PhCH2OH
A) oxidation
B) reduction
C) neither

Back 20

B) reduction

Front 21

25) Classify the reaction below as an oxidation, a reduction, or neither.
cis-pent-2-ene → pentane
A) oxidation
B) reduction
C) neither

Back 21

B) reduction

Front 22

26) Which of the following reagents is not typically viewed as an oxidizing agent?
A) Cl2
B) KMnO4
C) O2
D) KCl
E) H2O2

Back 22

D) KCl

Front 23

27) Which of the following compounds has carbon in the highest oxidation state?
A) CO2
B) CH3C(O)CH3
C) CH3CH2OH
D) CH3C(OCH2CH3)3

Back 23

A) CO2

Front 24

28) In the chromic acid oxidation of alcohols, the chromium is:
A) oxidized from Cr+3 to Cr+6.
B) reduced from Cr+6 to Cr+3.
C) oxidized from Cr+6 to Cr+3.
D) reduced from Cr+3 to Cr+6.
E) none of the above

Back 24

B) reduced from Cr+6 to Cr+3.

Front 25

29) Which of the following reagents is the best choice for oxidizing a primary alcohol to an aldehyde?
A) H2CrO4
B) pyridinium chlorochromate
C) Na2Cr2O7, H2SO4
D) KMnO4
E) LiAlH4

Back 25

B) pyridinium chlorochromate

Front 26

30) Which alcohol reacts most rapidly with the Lucas reagent?
A) benzyl alcohol
B) methanol
C) 2-propanol
D) isobutanol

Back 26

A) benzyl alcohol

Front 27

31) Which of the following catalysts is commonly used in industry to dehydrogenate alcohols?
A) CuO
B) Na
C) NaBH4
D) (CH3)2S
E) Zn

Back 27

A) CuO

Front 28

32) Which of the following oxidants will convert a primary alcohol to an aldehyde?
1) sodium dichromate /sulfuric acid 3) pyridinium chlorochromate
2) copper oxide 4) dimethylsulfoxide, oxalyl chloride
A) 3 and 4
B) 2, 3, and 4
C) 3
D) 1, 2, 3, and 4
E) none of the above

Back 28

B) 2, 3, and 4

Front 29

33) When (R)-butan-2-ol is treated with TsCl in pyridine, the product formed is:
A) a single enantiomer.
B) a racemic mixture.
C) a mixture of diastereomers.
D) an achial compound.
E) none of the above.

Back 29

A) a single enantiomer.

Front 30

34) What compound is produced when (R)-pentan-2-ol is treated with TsCl followed by NaI?
A) sodium (R)-pent-3-oxide
B) sodium (S)-pent-2-oxide
C) (R)-2-iodopentane
D) (S)-2-iodopentane
E) none of the above

Back 30

D) (S)-2-iodopentane

Front 31

35) Which of the following reactions or series of reactions would reduce 3-metylbutan-2-ol into 3-methylbutane?
A) 1. TsCl/pyridine 2. conc. KMnO4
B) 1. NaOCH3 2.. H2SO4/heat
C) 1. pyridinium chlorochromate 2. ZnCl2/HCl
D) 1. ZnCl2/HCl 2. t-butoxide/t-butanol
E) 1. TsCl/pyridine 2. LiAlH4

Back 31

E) 1. TsCl/pyridine
2. LiAlH4

Front 32

36) Which of the following alcohols will react most rapidly with the Lucas reagent
(HCl, ZnCl2)?
A) (CH3)3COH
B) CH3CH2CH2CH2OH
C) CH3CH(OH)CH2CH3
D) (CH3)2CHCH2OH

Back 32

A) (CH3)3COH

Front 33

37) Through what basic mechanism is 1-methylcyclohexanol converted to 1-bromo-1-methylcyclohexane upon treatment with HBr?
A) SN1
B) SN2
C) E1
D) E2
E) radical chain

Back 33

A) SN1

Front 34

38) What compound results when 1-butanol is treated with P/I2?
A) CH3CH2CH2CH2I
B) racemic CH3CH2CHICH3
C) CH3CH2CH2CH2OP(OH)2
D) CH3CH2CH2CH2PI2
E) Primary alcohols don't react with P/I2.

Back 34

A) CH3CH2CH2CH2I

Front 35

39) Which set of reagents will best convert 2,2-dimethylpropan-1-ol (neopentyl alcohol) to 4,4-dimethylpentan-2-ol?
A) 1. HCl 2. Mg 3. CH3CHO 4. H3O+
B) 1. HCl, ZnCl2 2. Mg 3. CH2O 4. H3O+
C) 1. SOCl2 2. Mg 3. CH3CHO 4. H3O+
D) 1. HCl, ZnCl2 2. Mg 3. CH3CHO 4. H3O+

Back 35

C) 1. SOCl2
2. Mg
3. CH3CHO
4. H3O+

Front 36

40) Given a sample of (R)-2,3-dimethylhexan-3-ol, which of the following would be the best synthesis of (R)-3-chloro-2,3-dimethylhexane?
A) HCl/ZnCl2
B) PCl3
C) SOCl2
D) 1. TsCl/Pyridine
2. NaCl
E) none of the above

Back 36

C) SOCl2

Front 37

41) Which of the following alcohols undergoes dehydration upon heating with concentrated H2SO4 without carbocation rearrangement?
A) 2-methylhexan-3-ol
B) 3-methylpentan-3-ol
C) 3,3-dimethylpentan-2-ol
D) 2-methyl-2-phenylpropan-1-ol
E) both A and B

Back 37

B) 3-methylpentan-3-ol

Front 38

42) Which of the following reaction series will result in the formation of a new secondary (2°) alcohol from the beginning alcohol listed at the top?
A) Ethanol 1. Na° 2. CH3CH2I
B) t-butyl alcohol 1. K2Cr3O7/acetic acid 2. CH3-MgBr 3. H3O+
C) 2-propanol 1. K2Cr3O7/acetic acid 2. CH3-MgBr 3. H3O+
D) n-butanol 1. H2SO4/heat 2. Hg(Ac)2 (aq) 3. NaBH4/alkalne
E) 2-methylcycloxexanol 1. H2SO4/heat 2. OsO4/H2O2 3. H2SO4/heat

Back 38

D) n-butanol
1. H2SO4/heat
2. Hg(Ac)2 (aq)
3. NaBH4/alkalne

Front 39

43) What class of organic compound is the major product of the acid catalyzed reaction of an alcohol with a carboxylic acid?
A) ether
B) ester
C) thiol
D) nitrile
E) sulfonate ester

Back 39

B) ester

Front 40

44) Which energetic material is a nitrate ester?
A) nitroglycerin
B) TNT
C) RDX
D) nitromethane

Back 40

A) nitroglycerin

Front 41

45) The Williamson ether synthesis proceeds via an __________ mechanism.
A) SN1
B) SN2
C) E1
D) E2
E) none of the above

Back 41

B) SN2

Front 42

6) What is the correct IUPAC name for the following structure?
A) (Z) 4-methyl-3-hexen-1-thiol
B) (Z) 6-mercapto-3-methylhex-3-ene
C) (E) 6-mercapto-3-methylhex-3-ene
D) (E) 4-methylhex-3-en-1-thiol

Back 42

A) (Z) 4-methyl-3-hexen-1-thiol

Front 43

16) Which of the following substrates will not form a Grignard reagent when treated with Mg/diethylether?

Back 43

B)

Front 44

20) Which of the following reactions will result in the formation of a secondary alcohol(s) in good yield?

Back 44

E) both A and D

Front 45

21) 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/heat
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. H2O/H3O+

Back 45

B) 1. NaBH4
2. H3PO4/heat

Front 46

46) Preferred RxN? Why?
A) Rxn B cuz oxidation works best for 1° alcohols.
B) Rxn A cuz smaller methyl iodide makes better nucleophilic target.
C) Rxn A cuz carbocation formation is stabilized by benzylic position.
D) Rxn B cuz Iodine is better leaving group for SN1.
E) No difference -- give approximately same yields.

Back 46

B) Reaction A is preferred over reaction B because the smaller methyl iodide would make a better nucleophilic target.