Unlock document.
This document is partially blurred.
Unlock all pages and 1 million more documents.
Get Access
114. Which of the compounds shown below would be the most likely product expected
from the reaction scheme shown?
?
(CH3)2CHCH(CH3)C
Br
Br
Br
Br
I II III IV V
CH excess Br2
CCl4
Br
Br Br
BrBr
Br
Br
Br
A) I
B) II
C) III
D) IV
E) V
115. The expected major product from treatment of 1-pentyne with excess HBr is:
A) 1,1-dibromo-1-pentene
B) 1,2-dibromo-1-pentene
C) 1,1-dibromopentane
D) 2,2-dibromopentane
E) 1,1,2,2-tetrabromopentane
116. For the reaction below, select the structure of the major organic product.
xs Br2?
I II III IV V
Br
Br Br
Br
Br
Br
Br
Br
Br
Br
Br Br
Br
A) I
B) II
C) III
D) IV
E) V
117. Select the expected major product(s) from the treatment of 1-pentyne with
1 equivalent of Br2.
A) 1,1-dibromo-1-pentene
B) (E)-1,2-dibromo-1-pentene
C) (Z)-1-bromo-1-pentene
D) A and B
E) B and C
118. Which of the following conditions effectively cleaves a carbon-carbon triple bond?
A) HgSO4 and aqueous H2SO4
B) 1) Disiamylborane 2) H2O2, NaOH
C) H2, Lindlar’s catalyst
D) 1) O3 2) H2O
E) Na, NH3(l)
119. Predict the major organic products of the reaction below.
1) O3
2) H2O
O
OH O
HO
CO
O
O
OH
?
I II III IV
A) I and II
B) II an III
C) I and IV
D) II and III
E) 1 and III
120. For the reaction sequence shown, what are the expected major organic products?
1. O3
2. H2O
I II III IV V
O
H
OO
OH
O
++ + + +
O
COHH3C
C OO H3C
O
OH HO
O
OH
?
OH O
C OO
H
A) I
B) II
C) III
D) IV
E) V
121. What are the expected major products of the reaction sequence shown below?
1. O3
2. H2O
?
III III IV V
O
OH
O
HO
O C OO O
A) I and II
B) I, III, and V
C) II, III, and IV
D) I and IV
E) II, III, IV
122. What is the expected major product of the reaction sequence shown below?
I II III IV V
1. O3
2. H2O
?
O
O
CO2H
CO2H
CO2H
O
O
O
O
A) I
B) II
C) III
D) IV
E) V
123. Ozonolysis of one mole of the compound shown is expected to produce how many
moles of CO2 upon completion of the reaction?
A) 1
B) 2
C) 3
D) 4
E) 8
124. Select the alkyne listed below that, upon treatment with ozone followed by water,
would not produce carbon dioxide and a carboxylic acid as the final products?
A) Ethyne
B) Propyne
C) 1-Butyne
D) 1-Pentyne
E) 1-Hexyne
125. Which of the following alkynes, upon ozonolysis, would be expected to produce
only one major organic product?
A) 1-Hexyne
B) 2-Hexyne
C) 3-Hexyne
D) 2-Heptyne
E) 3-Heptyne
126. Provide the IUPAC name for the alkyne expected to produce the two compounds
listed below upon ozonolysis?
CH3CH2CO2H and (CH3)3CCO2H
A) 1-tert-butyl-1-butyne
B) 2,2-dimethyl-3-hexyne
C) 3,3-dimethyl-2-hexyne
D) 5,5-dimethyl-3-hexyne
E) 3-octyne
127. Which alkyne would produce the products below upon ozonolysis?
OH
O
C OO
1. O3
2. H2O
?HO
O
OH
O
++
A) HC≡CC≡CCH2C≡CH
B) HC≡CCH2CHCH2C≡CH
C) CH3C≡CCH2C≡CCH3
D) HC≡CCH2CH2C≡CCH3
E) CH3C≡CC≡CC≡CH
128. What is the IUPAC name for the expected product of the transformation below?
1) NaNH2
2) CH3CH2CH2Br
H
H3C
A) Propyne
B) 1-Hexyne
C) 2-Hexyne
D) 3-Hexyne
E) (E)-3-Hexyne
129. What is the IUPAC name for the expected final product of the transformation
below?
1) NaNH2
2) CH3CH2CH2CH2Br
H
H
3) NaNH2
4) CH3CH2Br
?
A) 5-Decyne
B) 3-Hexyne
C) 1-Octyne
D) 3-Octyne
E) 5-Octyne
130. What is the expected major final product of the reaction sequence shown below?
1) NaNH2
CCH
H
3) NaNH2
4) CH3Br
2) Br
CC
?
III III IV V
CCCC
CC
CC
A) I
B) II
C) III
D) IV
E) V
131. What is the expected major final product of the reaction sequence shown below?
1) NaNH2
CCH
H
3) NaNH2
4)
2)
C
C
?
III III IV
CC
CC
CC
Br
Br
A) I
B) II
C) III
D) IV
E) None of the shown products will be produced.
132. What is the expected major product of the reaction sequence shown below?
HC≡C:– + (CH3)2CHCH2Br → ?
A) CH≡CH + (CH3)2CHC≡CH
B) (CH3)2CHC≡CCH3
C) (CH3)2CHCH2C≡CH
D) (CH3)2CHCHBrC≡CH
E) CH3CHCH2C≡CCH3
133. Which of the alkyl bromides listed would work as a reagent in step 2 of the reaction
sequence shown, with the resulting major product being an internal alkyne?
Br
Br
Br
Br
Br
III III IV V
1) NaNH2
2) R–Br
R
A) I and III
B) II and IV
C) III, IV, V
D) I, II, IV
E) II, III, V
134. Why would the following reaction sequence not produce the expected product
shown?
1) NaNH2
CCH
H
3) NaNH2
4) CH3Br
2) Br
CC
(NOT produced)
A) NaNH2 is used in the reduction of alkynes to trans alkenes.
B) The secondary alkylhalide would undergo an elimination reaction.
C) Br is not a good enough leaving group.
D) The terminal alkyne is not acidic enough to be deprotonated.
E) The reaction sequence is correct and will produce the shown product.
135. What is the final major product expected for the following reaction sequence?
H
H3C
1) NaNH2
2) (CH3)2CHCH2Br
3) Na, NH3(l)
?
I II III IV V
A) I
B) II
C) III
D) IV
E) V
136. Which of the compounds listed would be a final major product for the following
reaction sequence?
Br 1) 2 NaNH2
NH3
Br
III III IV V
Br
2) HBr
ROOR
?
Br
Br
Br
Br
A) I
B) II
C) III
D) IV
E) V
137. Which of the following methods would be expected to efficiently produce cis-2-
butene?
A) CH3CHBrCH2CH3 + (CH3)3COK/(CH3)3COH
B) CH3C≡CCH3 + H2, Pt
C) CH3C≡CCH3 + H2, Ni2B (P-2)
D) CH3C≡CCH3 + Na, NH3(l)
E) CH3CHBrCH2CH3 + NaNH2
138. Which sequence of reagents would be expected to accomplish the transformation
shown?
?
A) 1) HBr; 2) 2 NaNH2
B) 1) Br2; 2) 2 NaNH2
C) 1) Br2, H2O; 2) NaNH2
D) 1) HBr/ROOR; 2) excess NaNH2
E) 1) Na, NH3(l)
139. Which sequence of reagents would be expected to accomplish the transformation of
1-butyne shown below?
HC C CH2CH3
?HO
A) 1) H2O/H2SO4, HgSO4 cat.; 2) H2, Pt
B) 1) HBr; 2) H2, Pt; 3) NaOH
C) 1) H2, Lindlar catalyst; 2) BH3•THF; 3) H2O2, NaOH
D) 1) HBr, peroxides; 2) NaOH; 3) H2, Pt
E) 1) O3 2) H2O
140. Which sequence of reactions is expected to produce cis-3-octene as the final, and
major, organic product?
1) propyne, NaNH2
2) 1-bromopentane
3) aqueous H2SO4, cat. HgSO4
1) 1-butyne, NaNH2
2) 1-bromobutane
3) H2, Lindlar's cat.
III III
IV V
1) propyne, NaNH2
2) 1-bromopentane
3) H2, Ni2B (P-2)
1) 1-butyne, NaNH2
2) 1-bromobutane
3) Na, NH3(l)
1) 1-butyne, NaNH2
2) 1-bromobutane
3) H2, Pd/C
A) I
B) II
C) III
D) IV
E) V
141. Which sequence of reactions is expected to produce the product below as the final,
and major, organic product?
DOH
HO
D
H
H
?+ enantiomer
A) 1) H2, Lindlar’s cat.; 2) OsO4; 3) NaHSO3/H2O
B) 1) H2, Pt; 2) OsO4; 3) NaHSO3/H2O
C) 1) OsO4; 2) NaHSO3/H2O; 3) H2, Lindlar’s cat.
D) 1) Na, NH3(l); 2) OsO4; 3) NaHSO3/H2O
E) 1) OsO4; 2)NaHSO3/H2O; 3) Na, NH3(l)
142. Which sequence of reactions is expected to produce the product below as the final,
and major, organic product?
CH3
OH
HO
H
H
CH3
?+ enantiomer
A) 1) Na, NH3(l); 2) OsO4; 3) NaHSO3/H2O
B) 1) H2, Lindlar’s cat.; 2) MCPBA; 3) H3O+
C) 1) H2, Ni2B (P-2); 2) KMnO4, NaOH (cold)
D) Both A and B
E) Both A and C
143. Which sequence of reactions is expected to produce the product below as the final,
and major, organic product?
CH2CH3
Br
Br
H
H
?+ enantiomer
A) 1) Br2; 2) H2, Lindlar’s cat.
B) 1) H2, Lindlar’s cat.; 2) Br2
C) 1) Br2; 2) Na, NH3(l)
D) 1) Na, NH3(l); 2) Br2
E) 1) Br2, 2) H2, Pt
144. What is the final major product expected for the following reaction sequence?
1) H2, Ni2B (P-2) 2) Cl2
A) (R)-3-Chlorohexane
B) (S)-3-Chlorohexane
C) meso-3,4-Dichlorohexane
D) Racemic (2R,3R) and (2S,3S)-3,4-dichlorohexane
E) 2,3-Dichloro-3-hexene
145. What is the final major product expected for the following reaction sequence?
1) Na, NH3(l) 2) Br2
A) (R)-3-Bromohexane
B) (S)-3-Bromohexane
C) meso-3,4-Dibromohexane
D) Racemic (2R,3R) and (2S,3S)-3,4-dibromohexane
E) 2,3-Dibromo-3-hexene
146. Which sequence of reactions is expected to produce the product below as the final,
and major, organic product?
1) , NaNH2
2) (CH3)2CHCH2Br
3) aqueous H2SO4, cat. HgSO4
1) , NaNH2
2) (CH3)2CHBr
3) Disiamylborane
4) H2O2, NaOH
III III
IV V
1) (CH3)2CHBr, NaNH2
2)
3) O3
4) H2O
1) , NaNH2
2) (CH3)2CHCH2Br
3) BH3•THF
4) H2O2, NaOH
1) (CH3)2CHCH2Br, NaNH2
2)
3) 9-BBN
4) H2O2, NaOH
O
?
HC CH CH3C CH
CH3C CH
HC CH
CH3C CH
A) I
B) II
C) III
D) IV
E) V
147. Determine the possible number of alkynes with molecular formula C5H8.
A) one
B) two
C) three
D) four
E) five
148. Provide the systematic IUPAC name for CH3CH(CH3)C(CH3)2C≡CCH(CH3)2.
149. Provide the systematic IUPAC name for CH3C≡CC(CH3)2CH(CH2CH3)2.
150. Provide the systematic IUPAC name for CH3CHBrC≡C(CH2)3CH3.
151. Provide the systematic IUPAC name for the following compound:
152. Draw the line-bond structure for the compound with the IUPAC name: 2,5,9-
Trimethyl-2-decen-7-yne.
153. Rank the following hydrocarbons in order of decreasing acidity (most acidic to
least acidic).
I II III
A) I > II > III
B) I > III > II
C) II > III > I
D) II > I > III
E) III > I > II
F) III > II > I
154. Describe a sequence of reactions by which 2-hexyne can be straightforwardly
prepared from acetylene.
155. Determine the reagent(s) required to prepare trans-2-heptene from 2-heptyne?
A) H2, Pt
B) Na, NH3(l)
C) H2, Ni2B
D) NaOEt
E) H2SO4, H2O
156. Provide the reagent(s) expected to accomplish the transformation shown below:
C C CH2CH3
H3CH2CCH3(CH2)4CH3
?
A) H2, Pt
B) Na, NH3(l)
C) H2, Ni2B
D) NaOEt
E) H2SO4, H2O
157. Provide the reagent(s) expected to accomplish the transformation shown below:
C C
CH2CH3
C CCH3CH2CH2CH3
?
H3CH2C
HH
A) H2, Pt
B) Na, NH3(l)
C) H2, Ni2B
D) NaOEt
E) H2SO4, H2O
158. Determine which compound will react with sodium in liquid ammonia to form
trans-3-hexene.
A) cis-3-hexene
B) trans-2-hexene
C) 3-hexyne
D) 2-hexyne
E) cis-2-hexene
159. Provide the structure(s) of the expected major organic product(s) from the
following reaction:
HBr
ROOR
(CH3)2CHCH2C CH
160. Provide the structure(s) of the expected major organic product from the following
reaction:
CH3CH2C(CH3)2C CH 1) Disiamylborane
2) H2O2, NaOH
161. Provide the structure(s) of the expected major organic product(s) from the
following reaction:
1) O3
2) H2O
162. Provide the structure(s) of the expected major organic product from the following
reaction sequence:
Br
1) NaNH2
2)
3) H2
Lindlar's cat.
163. Which of the following best explains why the synthetic route shown below would
be unsuccessful?
1) CH3CH2Br
2) NaNH2
3) (CH3)3CBr
HC C CH3CH2C CC(CH3)3
A) The alkynide anion is not a strong enough nucleophile to react with 1-
bromopropane in step 1.
B) Sodium amide is not a strong enough base to deprotonate the terminal alkyne
in step 2.
C) The alkynide anion formed by reaction with sodium amide will facilitate an
E2 (rather than SN2) reaction with t-butyl bromide.
D) Both substitution reactions will occur on the same end of the alkyne, making a
product different than the one shown.
E) Reaction with sodium amide will result in formation of a primary alkyne.
