Exam 7: Organohalides: Nucleophilic Substitutions and Eliminations

Consider the reactions below to answer the following questions. a. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { F } \stackrel { \ominus \mathrm { OH } , \mathrm { H } _ { 2 } \mathrm { O } } { \longrightarrow } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH } + \mathrm { F } \Theta$ or b. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { I } \stackrel { \ominus \mathrm { OH } , \mathrm { H } _ { 2 } \mathrm { O } } { \longrightarrow } - \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH } + \mathrm { I } \Theta$ The mechanism for these reactions is: a. $\mathrm{S}_N1$ b. $\mathrm{S}_N2$ c. $\mathrm{E} 1$ d $E2$

Which mechanism is favored by the reaction of a secondary alkyl bromide with potassium t-butoxide?

Instructions: Draw the structure of the major organic products(s) for each of the following reactions. Indicate the stereochemistry for each reaction when appropriate.

Consider the following reaction: a) Draw the prochuct of the reaction. How would you cate gorize this process mechanistically? b) Which af the following spectral methods caud be used to follow the pargess of the reartigr?? a. NMR spectroscopy b. Mass spectrometry c. Infrared spectroscopy d. UV spectroscopy e. all of the se f. a, b, and c onlv

Consider the reactions below to answer the following questions. a. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { F } \stackrel { \ominus \mathrm { OH } , \mathrm { H } _ { 2 } \mathrm { O } } { \longrightarrow } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH } + \mathrm { F } \Theta$ or b. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { I } \stackrel { \ominus \mathrm { OH } , \mathrm { H } _ { 2 } \mathrm { O } } { \longrightarrow } - \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH } + \mathrm { I } \Theta$ Halving the concentration of hydroxide in these reactions: a. causes the reaction mechanism to change b. halves the rate of reaction c. has no effect on the rate of reaction d. doubles the rate of reaction

Instructions: For each question, draw a structure corresponding to the given name. Draw: 3-iodoprop-1-ene

Instructions: For each question, provide structures for the reactants, intermediates, or products, as indicated. Draw the structures in the boxes provided. Draw:

Instructions: Consider the reaction below to answer the following question(s). Refer to instructions. Draw a Newman projection of the reactive conformation of the starting material.

Instructions: Consider the reaction below to answer the following question(s). Refer to instructions. Compound B is the:

Instructions: Consider the pair of reactions below to answer the following question(s). Refer to instructions. The mechanism for these reactions is:

What is the IUPAC name of the following compound?

Propose a synthesis of the following compound from the given starting material and any inorganic reagents necessary.

Consider the reaction below to answer the following questions. Draw all the monochlorination products of methylcyclopentane (ignore stereoisomers).

Instructions: For each substrate below, choose which reaction type is favored. Place the letter of the reaction type in the blank above the substrate. a. $\mathrm{S}_N1$ b. $\mathrm{S}_N2$ c. $\mathrm{E} 1$ d $E2$ Refer to Instructions. _____ $\mathrm { RCH } _ { 2 } \mathrm { X } \stackrel { \mathrm { Nu } : } { \longrightarrow }$

Instructions: Consider the reaction below to answer the following question. Refer to instructions. The mechanism for this reaction is:

Instructions: Consider the reaction below to answer the following question(s). Refer to instructions. Write the product that results from the indicated electron flow in the reaction, showing any resulting stereochemistry

Instructions: Circle the correct response in each set below. Refer to instructions. The least reactive compound in an S_N2 reaction. Explain your choice.

Instructions: Provide a IUPAC name for each of the following alkyl halides. Name:

Which of the following statements about an S_N2 reaction is true?

Instructions: For each question, provide structures for the reactants, intermediates, or products, as indicated. Draw the structures in the boxes provided. Draw: