
a)
Interpretation:
Assuming that halogens add to
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.
b)
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.
c)
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.

Trending nowThis is a popular solution!

Chapter 9 Solutions
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
- What is the stepwise mechanism for this reaction?arrow_forward32. Consider a two-state system in which the low energy level is 300 J mol 1 and the higher energy level is 800 J mol 1, and the temperature is 300 K. Find the population of each level. Hint: Pay attention to your units. A. What is the partition function for this system? B. What are the populations of each level? Now instead, consider a system with energy levels of 0 J mol C. Now what is the partition function? D. And what are the populations of the two levels? E. Finally, repeat the second calculation at 500 K. and 500 J mol 1 at 300 K. F. What do you notice about the populations as you increase the temperature? At what temperature would you expect the states to have equal populations?arrow_forward30. We will derive the forms of the molecular partition functions for atoms and molecules shortly in class, but the partition function that describes the translational and rotational motion of a homonuclear diatomic molecule is given by Itrans (V,T) = = 2πmkBT h² V grot (T) 4π²IKBT h² Where h is Planck's constant and I is molecular moment of inertia. The overall partition function is qmolec Qtrans qrot. Find the energy, enthalpy, entropy, and Helmholtz free energy for the translational and rotational modes of 1 mole of oxygen molecules and 1 mole of iodine molecules at 50 K and at 300 K and with a volume of 1 m³. Here is some useful data: Moment of inertia: I2 I 7.46 x 10- 45 kg m² 2 O2 I 1.91 x 101 -46 kg m²arrow_forward
- K for each reaction step. Be sure to account for all bond-breaking and bond-making steps. HI HaC Drawing Arrows! H3C OCH3 H 4 59°F Mostly sunny H CH3 HO O CH3 'C' CH3 Select to Add Arrows CH3 1 L H&C. OCH3 H H H H Select to Add Arrows Q Search Problem 30 of 20 H. H3C + :0: H CH3 CH3 20 H2C Undo Reset Done DELLarrow_forwardDraw the principal organic product of the following reaction.arrow_forwardCurved arrows are used to illustrate the flow of electrons. Using the provided structures, draw the curved arrows that epict the mechanistic steps for the proton transfer between a hydronium ion and a pi bond. Draw any missing organic structures in the empty boxes. Be sure to account for all lone-pairs and charges as well as bond-breaking and bond-making steps. 2 56°F Mostly cloudy F1 Drawing Arrows > Q Search F2 F3 F4 ▷11 H. H : CI: H + Undo Reset Done DELLarrow_forward
- Calculate the chemical shifts in 13C and 1H NMR for 4-chloropropiophenone ? Write structure and label hydrogens and carbons. Draw out the benzene ring structure when doing itarrow_forward1) Calculate the longest and shortest wavelengths in the Lyman and Paschen series. 2) Calculate the ionization energy of He* and L2+ ions in their ground states. 3) Calculate the kinetic energy of the electron emitted upon irradiation of a H-atom in ground state by a 50-nm radiation.arrow_forwardCalculate the ionization energy of He+ and Li²+ ions in their ground states. Thannnxxxxx sirrr Ahehehehehejh27278283-4;*; shebehebbw $+$;$-;$-28283773838 hahhehdvaarrow_forward
- Plleeaasseee solllveeee question 3 andd thankss sirr, don't solve it by AI plleeaasseee don't use AIarrow_forwardCalculate the chemical shifts in 13C and 1H NMR for 4-chloropropiophenone ? Write structure and label hydrogens and carbonsarrow_forwardPlease sirrr soollveee these parts pleaseeee and thank youuuuuarrow_forward
- Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning



