EP ORGANIC CHEMISTRY,24 MONTH-OWLV2
EP ORGANIC CHEMISTRY,24 MONTH-OWLV2
9th Edition
ISBN: 9781305084391
Author: McMurry
Publisher: CENGAGE L
Question
Book Icon
Chapter 9.SE, Problem 18MP
Interpretation Introduction

a)

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 9.SE, Problem 18MP , additional homework tip  1

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br2 adds to 2-butyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the halogens to yield a tetrahaloalkane derivative. In the first step of the addition reaction the nucleophilic attack of the π electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br2 adds to 2-butyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Interpretation Introduction

b)

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 9.SE, Problem 18MP , additional homework tip  2

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Cl2 adds to 1-phenylpropyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction, the nucleophilic attack of the π electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Cl2 adds to 1-phenylpropyne assuming that chlorine adds to alkynes in the same manner as they add to alkenes.

Interpretation Introduction

c)

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 9.SE, Problem 18MP , additional homework tip  3

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br2 adds to 1-pentyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction the nucleophilic attack of the π electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br2 adds to 1-pentyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Blurred answer
Students have asked these similar questions
A solution contains 0.097 M Ce3+, 1.55x10-3 M Ce4+, 1.55x10-3 M Mn2+, 0.097 M MnO4-, and 1.00 M HClO4 (F= 9.649 x 104 C/mol). a) Write a balanced net reaction that can occur between species in this solution. b) Calculate deltaG0 and K for the reaction. c) Calculate E and deltaG for the conditions given. Ce4+ + e- = Ce3+  E0= 1.70 V MnO4- + 8H+ + 5e- = Mn2+ + 4H2O   E0= 1.507 V
1. Provide a step-by-step mechanism for formation of ALL STEREOISOMERS in the following reaction. Na HCO3 (Sodium bicarbonate, baking soda) is not soluble in CH2Cl2. The powder is a weak base used to neutralize strong acid (pKa < 0) produced by the reaction. Redraw the product to show the configuration(s) that form at C-2 and C-4. Br2 OH CH2Cl2 Na* HCO3 Br HO OH + Na Br +
2. Specify the solvent and reagent(s) required to carry out each of the following FGI. If two reagent sets must be used for the FGI, specify the solvent and reagent(s) for each reagent set. If a reaction cannot be carried out with reagents (sets) class, write NP (not possible) in the solvent box for reagent set #1. Use the letter abbreviation for each solvent; use a number abbreviation for reagent(s). Solvents: CH2Cl2 (A); H₂O (B); Reagents: HBr (1); R₂BH (6); H2SO4 (2); CH3OH (C); Br₂ (3); CH3CO₂H (D) NaHCO3 (4); Hg(OAc)2 (5); H₂O2/HO (7); NaBH4 (8) Reagent Set #1 Reagent Set #2 FGI + enant OH Solvent Reagent(s) Solvent Reagent(s)

Chapter 9 Solutions

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2

Ch. 9.8 - Prob. 11PCh. 9.9 - Show the terminal alkyne and alkyl halide from...Ch. 9.9 - Beginning with acetylene and any alkyl halide...Ch. 9.SE - Name the following alkynes, and predict the...Ch. 9.SE - From what alkyne might each of the following...Ch. 9.SE - Prob. 16VCCh. 9.SE - The following cycloalkyne is too unstable to...Ch. 9.SE - Prob. 18MPCh. 9.SE - Assuming that strong acids add to alkynes in the...Ch. 9.SE - Prob. 20MPCh. 9.SE - Prob. 21MPCh. 9.SE - Prob. 22MPCh. 9.SE - Prob. 23MPCh. 9.SE - Prob. 24MPCh. 9.SE - Reaction of acetone with D3O+ yields...Ch. 9.SE - Give IUPAC names for the following compounds:Ch. 9.SE - Draw structures corresponding to the following...Ch. 9.SE - Prob. 28APCh. 9.SE - Prob. 29APCh. 9.SE - Prob. 30APCh. 9.SE - Predict the products from reaction of l-hexyne...Ch. 9.SE - Prob. 32APCh. 9.SE - Prob. 33APCh. 9.SE - Propose structures for hydrocarbons that give the...Ch. 9.SE - Identify the reagents a-c in the following scheme:Ch. 9.SE - Prob. 36APCh. 9.SE - Prob. 37APCh. 9.SE - Prob. 38APCh. 9.SE - How would you carry out the following...Ch. 9.SE - Prob. 40APCh. 9.SE - Synthesize the following compounds using 1-butyne...Ch. 9.SE - Prob. 42APCh. 9.SE - Prob. 43APCh. 9.SE - Prob. 44APCh. 9.SE - Prob. 45APCh. 9.SE - A hydrocarbon of unknown structure has the formula...Ch. 9.SE - Compound A(C9H12) absorbed 3 equivalents of H2 on...Ch. 9.SE - Hydrocarbon A has the formula C12H8. It absorbs 8...Ch. 9.SE - Occasionally, a chemist might need to invert the...Ch. 9.SE - Prob. 50APCh. 9.SE - Prob. 51APCh. 9.SE - Prob. 52APCh. 9.SE - Prob. 53APCh. 9.SE - Prob. 54APCh. 9.SE - Prob. 55APCh. 9.SE - Prob. 56APCh. 9.SE - Prob. 57AP
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Text book image
Pushing Electrons
Chemistry
ISBN:9781133951889
Author:Weeks, Daniel P.
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning