ORGCHEM LEC REVIEWER 6.

Which of these statements is false regarding the

2ND TERM following reaction?
1. Which of the following compounds is the most
acidic?
a. Butane
b. 2-butanone
c. 1-butanone
d. butanal

2. Which of the following structures is a hemiacetal?

a. the nucleophile is a carbon in the Grignard reagent.
b. the Grignard reaction is a nucleophilic addition
reaction
c. the product has on chiral center and is optically
active
a. b. d. water cannot replace THF as the solvent

7. In the imine formation of the following product is the

result of a reaction between which two molecules?

c. d.
3. Which of the following has the highest boiling point?
a. Butanol
b. Propanal
c. Propanol
d. Butanal

4. Tollen’s reagent, Ag+Ag+start text, A, g, end text,

start superscript, plus, end superscript , is an a.
oxidation agent. What are the products of Tollen’s
reagent reaction with the following molecule?

b.

c.

a. propanol and Ag+

b. propanoic acid and Ag+
c. propanol and Ag d.
d. propanoic acid and Ag
8. Which of the following is a false statement about the
5. What reagents, in an acidic environment, could be following aldol condensation reaction?
used to synthesize the ketal shown below? a. The final step in the reaction is the formation of an
α-β-unsaturated carbonyl through decarboxylation
b. The first step of a base catalyzed aldol
condensation is the deprotonation of the alpha
a. acetaldehyde and methanol
hydrogen to activate the nucleophile.
b. acetone and methanol
c. If R and R’ in reactant I were both methyl groups
c. acetone and methanol
and R’’ and R’’’ in reactant II were both phenyl
d. formaldehyde and propanol
groups, the reaction will only yield one product.
d. Product III can undergo a nucleophilic conjugate
addition reaction.
 d.) reaction of a terminal alkyne with water in the
9. The following molecule can be synthesized from a presence of H2SO4 and HgSO4
diol and a ketone under an acid catalyst. Which of the e.) all of the above methods could be used
following accounts for the oxygen atoms in this
molecule? 13. Product B of the following sequence of reactions
would be: e

a. both oxygen atoms come from water in the solvent

b. both oxygen atoms come from the diol
c. both oxygen atoms come from the ketone
d. one oxygen atoms comes from the ketone and the
other comes from the diol 14. What reagent(s) would you use to accomplish the
following reaction?
10. The following molecule is reacted with LiAlH4. The
product is then reacted with formaldehyde under
acidic conditions, what will be the product?
a.) H3O+/H2O
b.) LiAlH4/ H3O+
c.) NaBH4/H3O+
d.) B2H6, H2O2/KOH
e.) H2/Pd

15. Which of the following procedures could be used to

prepare 1-phenyl-2-methyl-2-butanol

a. b.

c. d.

a.) I&II
11. Which reagent would you use to convert citronellol
b.) II&III
to citronellal, the chief constituent of citronella oil?
c.) III&IV
d.) I&III
e.) I&IV
a.) KOH
b.) KMnO4
16. Which of the following compounds can be reduced
c.) PCC/CH2Cl2
with lithium aluminum hydride to give 2- methyl -1-
d.0 LiAlH4
propanol (CH3)2CHCH2OH
I. (CH3)2CHCH3
12. Which of the following methods could not be used to
II. (CH3)2CHCH = O
make a methyl ketone (a ketone in which one of the
III. (CH3)2CHCOOH
alkyl groups is methyl)?
IV. (CH3)2C = CH2
a.) oxidation of an alcohol
a.)I and II
b.) reaction of a carboxylic acid chloride with a
b.) II and III
diorganocopper (Gilman) reagent
c.) III and IV
c.) Friedel-Crafts acylation
d.) II and IV
17. Which product would be formed after workup with 22. Acetals are sometimes formed from aldehydes and
dilute sulfuric acid when an excess of ketones to function as“protecting groups.” If one
phenylmagnesium bromide, Ph –Mg-Br, reacts with mole of 1,2-ethanediol (ethylene glycol) were to react
methyl benzoate, PhCOOCH3? with the compound to the right, which of the
a.) Ph3C-OH (Ph =phenyl) carbonyl groups would be protected?
b.) Ph2CH- OH
c.) Ph –CO-Ph
d.) Ph3CH

18. Which of the following functional groups cannot be a.)I

present in a halogen- containing compound you wish b.) II
to react with magnesium to form a Grignard reagent? c.) III
I. -COOH II. - COCH3 III.-OH- d.)I and II
a.) I e.) II and III
b.) II
c.) III 23. Rank the protons in 3,5 heptanedione in order of
d.) I and II decreasing acidity ( most acidic first)
e.) I,II,and III

19. Which of the following reagents would be most

successful at converting 1-pentanol to pentanal,
CH3CH2CH2CH2CH=O? a.) I>II>III
a.) KMnO4 b.) III>II>I
b.) CrO3/H2SO4 c.) II>III>I
c.) Na2CrO4/H2SO4 d.) II>I>III
d.) C5H6NCrO3Cl (PCC)/CH2Cl2
24. Which of the following could be employed to
20. Select the principal product of the following transform ethanol into CH3CH2CH2OH
synthesis. a.) Ethanol + HBr, then Mg/diethyl ether, then H3O+
b.) Ethanol, HBr, then Mg/diethyl ether, then HCOH,
then H3O+
c.) Ethanol + H2SO4 (140oC)
a.) Ph- CH =NH
d.) Ethanol + Na, then HCOH, then H3O+
b.) Ph - CH2CN
e.) ethanol + H2SO4(180oC), then ethylene oxide
c.) Ph-CH2COOH
d.) PhCH(OH)- COOH
25. Which Wittig reagent could be used to synthesize
C6H5 CH = CH CH2CH3?
21. Which of the following sets of reagents and
a.) C6H5CHP+(C6H5)3
conditions could not accomplish the transformation
b.) C6H5 CH =CHCHP+(C6H5)3
shown below
c.) CH3CH2CHP+(C6H5)
(I) H2N-NH2, KOH, diethylene glycol solvent, heat,
d.) more one than of these
(II) 1. NaBH4, 2. H3O+
(III) HOCH2CH2OH, H3O+
26. Which compound is an acetal ?
(IV) 1. LiAlH4, 2. H2O

a
a.) I and II
b
b.) I and IIII
c
c.) I and IV
d
d.) II and III
e.) II, III and IV
27. Which would be formed in the following reaction?
 a.) CH3CHOHCH2CHO
b.) CH3CH2CH(OH)CH(CH3)CHO a.) III only
c.) CH3CH(OH)CH(CH3)CHO b.) Both I and III
d.) CH3CH2CH(OH)CH2CHO c.) Both I and II
e.) all of these will be formed d.) Both II and III

28. What would be the major product of the following 33. The product formed by the reaction of an aldehyde
reaction? with a primary amine is
a.) Carboxylic acid
b.) Aromatic acid
c.) Schiffs base
d.) Ketone

34. Cannizaro’s reaction is not given by ____________

a.)
b.)
c.)
d.) 35. Correct order of decreasing reactivity of nucleophilic
addition in case of HCHO, CH3CHO, CH3COCH3 is
29. Reduction of aldehydes and ketones into a.)CH3 COCH3 > CH3CHO > HCHO
hydrocarbons using zinc amalgam and conc. HCl is b.) HCHO > CH3CHO > CH3COCH3
called: c.) CH3COCH3 > HCHO > CH3CHO
a.) Cope reduction d.) CH3CHO > HCHO > CH3COCH3
b.) Dow reduction
c.) Wolff-Kishner reduction 36. In the following question one or more options may be
d.) Clemensen reduction correct. Which of the following compounds do not
undergo aldol condensation? B and d
30. Acetophenone when reacted with base C2H5—ONa,
yields a stable product:
37. Benzophenone (C6H5)2CO can be obtained by
____________
a.) Benzoyl chloride (C6H5)COCl + Benzene +
AlCl3
a.) b.) Benzoyl chloride + Phenyl magnesium chloride
b.) c.) Benzene + Carbon monoxide + ZnCl2
c.)
d.) 38. For distinction between pentan-2-one and pentan-3-
one, which reagent can be employed?
31. CH3CHO and C6H5 CH2CHO can be distinguished a.) K2Cr2O7/H+
chemically by b.) ZnHg/HCl
a.) Benedict’s test c.) NaOH/I2
b.) Iodoform test d.) AgNO3/NH4OH
c.) Tollen’s reagent test
d.) Fehling’s solution test 39. Which of the following will undergo aldol
condensation?
32. Which among the given molecules can exhibit a.) CH2 = CHCHO
tautomerism? b.) CH = CCHO (triple bond)
c.) C6H5CHO
d.) CH3CH2CHO
40. Compound ‘A’ C5H10 O forms a phenyl hydrazone (b) the carboxylate anion is destabilized by resonance
and gives a negative Tollen’s reagent test and to a greater extent than the carboxyl group and
iodoform test. On reduction with Zn+Hg/HCl, neither the alcohol nor its alkoxide anion is
compound A gives n- pentane. The compound ‘A’ is destabilized by resonance.
a.) Primary alcohol (c) the carboxyl group is very unstable because of a
b.) Aldehyde high energy C-O bond and it therefore ionizes
c.) Secondary alcohol readily.
d.) Ketone (d) the carboxyl group is stabilized by resonance to a
greater extent than the carboxylate anion and neither
41. Tert Butyl alcohol can be obtained by treating with the alcohol nor its alkoxide anion is stabilized by
CH3MgBr followed by hydrolysis resonance.
a.) HCHO (e) Way bogus, dude! Alcohols are like way more
b.) CH3CHO acidic than carboxylic acids.
c.) CH3COCH3
d.) CH3CH2CHO 45. Which of the following syntheses would not give an
acceptable yield of the indicated carboxylic acid
42. Which of the following is the correct representation
for intermediate of nucleophilic addition reaction to
the given carbonyl compound (A):

a.)
b.)
c.) (a) I, (b) II, (c) III, (d) IV, (e) I&II, (f) III&IV, (g)
d.) both a and b I&III, (h) II&IV

43. Aldehydes differ from ketones in that they 46. The correct order of acidity of the acids shown below
(I) are less reactive than ketones toward nucleophilic (most acidic first) is
addition reactions.
(II) are more reactive than ketones toward
nucleophilic addition reactions.
(III) are less reactive than ketones toward
nucleophilic substitution reactions.
(IV) are more reactive than ketones toward
nucleophilic substitution reactions.
(a) I>II>III>IV
(V) are less easily oxidized than ketones.
(b) II>IV>I>III
(VI) are more easily oxidized than ketones.
(c) IV>II>I>III
(a) I&III
(d) IV>III>II>I,
(b) I,III&V
47. Which reagents would affect the conversion shown?
(c) II&IV
(d) II, IV, &VI
(e) I&V
(f) II&VI
(g) None of the previous answers is correct
(a) CH3MgBr/ether, then H3O+
44. Carboxylic acids are stronger acids than alcohols
(b) CH3 Li/ether, then H3O+
because
(c) CH3Br/AlCl3
(a) the carboxylate anion is stabilized by resonance to
(d) (CH3 )2CuLi/ether,
a greater extent than the carboxyl group and neither
the alcohol nor its alkoxide anion is stabilized by
resonance.
48. Which compounds shown below are correctly named (d) Na2CrO4
in the IUPAC system as pentane based, either as
pentanals or pentanones 53. Predict the major products of the following reaction

(a) I, (b) II, (c) III, (d) I&III, (e) None of them.

49. A common reaction type for aldehydes and ketones is

(a) electrophilic substitution
(b) nucleophilic substitution
(c) nucleophilic addition
(d) oxidation 54. Select the major product of the following reaction
(e) None of the previous answers is correct.

50. Predict the major organic product(s) in the following

reaction

55. Rank the following compounds in order of decreasing

reactivity in a Williamson synthesis (most reactive
first).
(I) bromomethane
(II) 1-bromopropane
(III) 2-bromopropane, (IV) 2-bromo-2-
(a) I methylpropane
(b) II (a) I>II>III>IV
(c) I&II in equal amount (b) IV>III>II>I
(d) I&II in unequal amount (c) III>II>I>IV
(d) II>III>IV>I
51. Predict the major organic product(s) in the following
reaction. 56. Select the best name for the compound

(a) I
(b) II&III in equal amount, (a) diethyl ether
(c) II&III in unequal amount (b) diisopropyl ether
(d) IV&V in equal amount (c) dipropyl ether
(d) dipropyl ketone
52. What reagent would you use to effect the (e) disec-propyl ether
transformation shown
57. The ether shown in question #1 can be synthesized by
bimolecular dehydration as shown to the right. Which
of the following compounds is most likely to be a
significant byproduct in such a synthesis?
(a) H2 SO4
(b) NaBH4
(c) KOH
58. Which of the following ethers could not be
synthesized by a Williamson synthesis?