Name__________________________________________________________ Alkyl Halide 1. Provide IUPAC name for alkyl halide.

CHI3 (iodoform) Draw a structure corresponding to the given name. 3-iodoprop-1-ene Draw trans-1-sec-butyl-3-chlorocyclohexane

SN_____

2.

3.

Consider the reaction below to answer the following question(s).

4. Write the product that results from the indicated electron flow in the reaction, showing any resulting stereochemistry.

5. Which is most reactive in an SN1 reaction? Explain your choice.

a.

b. CH3I

c.

d.

e.

6. Consider the following compound:

a)

What is the IUPAC name of the compound? a. (R)-1-chloro-3-methyl-2-cyclohexene b. (S)-1-chloro-3-methyl-2-cyclohexene c. (R)-3-chloro-1-methylcyclohexene d. (S)-3-chloro-1-methylcyclohexene How could this compound be used to produce a conjugated diene?

b)

a. substitution b. elimination c. allylic free radical formation d. either b or c

7. Predict the product of the following reaction:

8. Consider the following reaction:

a) b)

Draw the product of the reaction. How would you categorize this process mechanistically? Which of the following spectral methods could be used to follow the progress of the reaction? a. NMR spectroscopy b. Mass spectrometry c. Infrared spectroscopy d. UV spectroscopy e. all of these f. a, b, and c only

Consider the reaction below to answer the following questions.

9.

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

10.

Which reaction would be predicted to be faster? Explain.

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

11.

12. 13. Grignard Reagents are prepared by reaction of: a. b. c. d. an alkyl halide with magnesium in ether solvent. an alkyl halide with cuprous iodide in ether solvent. an alkyl halide with lithium metal in ether solvent. all of the above reactions prepare Grignard reagents.

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. b. c. d. SN1 SN2 E1 E2

14. Refer to Instructions. _____

15. Refer to Instructions. _____

Multiple Choice Identify the choice that best completes the statement or answers the question. Consider the pair of reactions below to answer the following question(s). a.

or b.

____ 16. Refer to instructions. The alkyl bromide starting materials in these reactions are classified as: a. 30 b. 20 c. 10 d. 40

____ 17. Refer to instructions. The nucleophile in these reactions is: + a. K b. alkyl group c. Br d. I

____ 18. Refer to instructions. The mechanism for these reactions is: a. SN2 b. E2 c. SN1 d. E1

Instructions: Consider the reaction below to answer the following question.

____ 19. Refer to instructions. The mechanism for this reaction is: a. SN2 b. E2 c. SN1 d. E1

Instructions: Consider the reaction below to answer the following question(s).

____ 20. Refer to instructions. Compound C is the: a. SN2 product b. SN1 product c. E2 product d. E1 product

Instructions: Consider the reaction below to answer the following question(s).

____ 21. Refer to instructions. The mechanism of this reaction is: a. SN1 b. SN2 c. E1 d. E2

____ 22. Which of the following statements about an SN1 reaction is true? a. the reaction occurs in one-step b. there is no effect on reaction rate by nucleophile c. primary alkyl halides react faster than secondary alkyl halides d. the reaction proceeds with inversion of stereochemistry e. the reaction is favored by aprotic solvents

____ 23. Which mechanism is favored by the reaction of a tertiary alkyl chloride with ethanol? a. SN1 b. SN2 c. E1 d. E1CB e. E2

____ 24. Which mechanism is favored by the reaction of a secondary alkyl bromide with potassium t-butoxide? a. SN1 b. SN2 c. E1 d. E1CB e. E2

____ 25. What is the rate law for the E2 reaction of an alkyl halide (RX) with sodium ethoxide (NaOEt) in ethanol solvent (EtOH)? a. rate = k[RX] 2 b. rate = k[RX] + c. rate = k[RX][Na ] d. rate = k[RX][OEt ] e. rate = k[OEt ]