Acid/Base 1. Which of the following is the most acidic? HCN (pKa = 9.31) H3PO4 (pKa = 2.

16) A) HCN B) H3PO4 C) H2O D) CH3CO2H Hybridization 2.

H2O (pKa = 15.74)

CH3CO2H (pKa = 4.76)

What is the correct hybridization state for atom 1 in the molecule above? A) sp2 B) sp3 C) sp D) s 3.

What is the correct hybridization state for atom 4 in the molecule above? A) sp2 B) sp3 C) sp D) s Nomenclature 4. what is the correct name for the molecule below?

A) 2,4-dimethylcyclopentane B) 1,4-diemthylcyclopentane C) 1,3-dimethylcyclopentane D) 3,5-diemthylcyclopentane 5. What is the correct name for the molecule below?

A) 1,5-dimethyl-2-ethylcyclohexane B) 1,5-dimethyl-4-ethylcyclohexane C) 1-ethyl-2,4-dimethylcyclohexane D) 1,3-dimethyl-4-ethylcyclohexane 6. Which of the following is an acceptable name for the compound below?

A) cis-1,2-dimethylcyclopentane B) cis-1-methyl-2-methylcyclohexane C) trans-1,2-dimethylcyclopentane D) trans-1-methyl-2-methylcyclohexane 7. Which of the following correctly represents the chair conformation of trans-1-chloro-3-methylcyclohexane?

A)

B)

C)

D) 8. Which of the following correctly represents cis-1-ethyl-2-methylcyclohexane?

A)

B)

C)

D) 9. What is the correct name for the structure below?

A) (E)-5-propyl-3,9-decadiene B) (E)-3,3-dimethyl-4-propyl-1,5-octadiene C) (Z)-3,3-dimethyl-4-propyl-1,5-octadiene D) (Z)-5-propyl-3,9-decadiene Aromatics 10. Identify the following as orthro-, meta-, or para- substituted.

A) orthoB) metaC) para11. What is the common name of the compound below?

A) phenol B) toluene C) benzoic acid D) acetophenone 12.

Select the correct IUPAC name for the compound below.

A) m-isopropylmethylbenzene B) o-isopropylmethylbenzene C) p-sec-propylmethylbenzene D) m-sec-propylmethylbenzene 13. Which of the following is another accepted name for 1,2-dimethylbenzene? A) o-methyltoluene B) m-xylene C) 3,4-dimethylbenzene D) 1,2-diemthylcyclohexene Oxidation/Reduction 14. Which of the following is the least oxidized?

A) A B) B C) C D) D Degrees of Unsaturation 15.

What is the degree of unsaturation for the following compound? C6H12O3 A) 3 B) 0 C) 4 D) 1 16. What is the degree of unsaturation for the following compound? C10H14N2 A) 5 B) 4 C) 3 D) 1 Reactions: 2 points each 17.

A) A B) B C) C D) D 18. Which of the following will be the major product(s)?

A) A B) B C) C D) A and B E) A and C 19.

A) A B) B C) C

D) D E) C and D 20. Indicate the major product.

A) A B) B C) C D) D 21.

A) A B) B C) C D) D 22.

A) A B) B C) C D) D 23. Which of the following reagents would be used to accomplish the following reactions?

A) Dess-Martin Periodinane B) CrO3 24. Which of the following reagents would be used to accomplish the following reactions?

A) Dess-Martin Periodinane B) CrO3 25.

A) A B) B C) C D) D 26.

A) A B) B C) C D) D 27.

A) A B) B C) C D) D 28.

A) A

B) B C) C D) D 29.

A) A B) B C) C D) D 30.

A) A

B) B C) C D) D Synthesis: 2 points each

How would you synthesize the following, assumng o, m, and p isomers can be isolated?

31.

A) EFC B) CEF C) FEC D) ECF 32.

A) DMI B) DGI C) DIG D) DIM Synthesis: 2 points

33. Using the letters above, how would the following synthesis take place?

A) NOF B) NG C) ENG D) MG