organic chemstry

HW 9 Total points: 100 Answer the following questions: 1) Which of the following describes the carbon-chlorine bond of an alkyl chloride? A) nonpolar; no dipole B) polar; δ+ at carbon and δ- at chlorine C) polar; δ- at carbon and δ+ at chlorine D) ionic E) none of the above 2) What are the substitution products of the following reaction? CH3CH2Br + -OH → ? A) CH3CH2BrH+ + O- B) HOCH2CH2Br C) CH3CH2OH + Br-

D) CH2 CH2 + Br- + H2O E) CH2 CHBr + H2O 3) Draw the product that is formed when (S)-2-iodopentane reacts with KCN. 4) Draw the major product of the following reaction:

5) Draw the major product of the following reaction:

6) What is the leaving group in the reaction shown below?

A) I B) II C) III D) IV E) V 7 ) Name the products of the following SN2 reactions:

8) What is the major product of the following E2 reaction?

A)

B) CH3CH2CH CH2 C)

D)

E)

9) Draw all possible alkene products and circle the major product:

10) Write the name of the missing alkyl halide reactant in the elimination reactions shown below.

11) What is the major product of the following E2 reaction?

A)

B)

C)

D)

E) no reaction 12) Draw the major product of the following reaction:

13) Draw the product of the following reaction:

]

14) What sequence of regents would you need to obtain the following product from 1-bromo- 1,4,4-trimethylcyclohexane?

Answer: 1. CH3ONa 2. O3 3. Me2S 15) Which alkyl halide reacts the fastest in a E1 reaction? A)

B) CH2 CHCl C)

D)

E) CH3CH2CH2Cl

18) Which of the compounds shown below is the product of this reaction?

A) I only B) II only C) I and II are of equal yield. D) I is major, II is minor. E) I is minor, II is major. 19) Which alkyl halide reacts fastest in an E2 reaction? A)

B) CH3CH2CH2Cl C) CH3CH2CH2I D)

E) CH3CH2CH2Br 20) What is the major product of the following reaction?

A) 2,3-dimethyl-1-hexene B) 2,3-dimethyl-2-hexene C) 2-isopropyl-1-pentene D) (Z)-2,3-dimethyl-3-hexene E) (E)-2,3-dimethyl-3-hexene