Chemistry Chapter 10 3 Which of the compounds shown below would be the most likely

114. Which of the compounds shown below would be the most likely product expected

from the reaction scheme shown?

?

(CH3)2CHCH(CH3)C

Br

I II III IV V

CH excess Br2

CCl4

Br

Br Br

BrBr

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

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

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

CO2H

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

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

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

?

III III IV

CC

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

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

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

?+ 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

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

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.