Acid/Base

1.Which of the following is the most acidic?HCN (pKa = 9.31) H3PO4 (pKa = 2.16) H2O (pKa = 15.74) CH3CO2H (pKa = 4.76)A) HCNB) H3PO4C) H2OD) CH3CO2HHybridization

2.

What is the correct hybridization state for atom 1 in the molecule above?A) sp2B) sp3C) spD) s3.

What is the correct hybridization state for atom 4 in the molecule above?A) sp2B) sp3C) spD) sNomenclature

4.what is the correct name for the molecule below?

A) 2,4-dimethylcyclopentaneB) 1,4-diemthylcyclopentaneC) 1,3-dimethylcyclopentaneD) 3,5-diemthylcyclopentane5.What is the correct name for the molecule below?

A) 1,5-dimethyl-2-ethylcyclohexaneB) 1,5-dimethyl-4-ethylcyclohexaneC) 1-ethyl-2,4-dimethylcyclohexaneD) 1,3-dimethyl-4-ethylcyclohexane6.Which of the following is an acceptable name for the compound below?

A) cis-1,2-dimethylcyclopentaneB) cis-1-methyl-2-methylcyclohexaneC) trans-1,2-dimethylcyclopentaneD) trans-1-methyl-2-methylcyclohexane7.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-decadieneB) (E)-3,3-dimethyl-4-propyl-1,5-octadieneC) (Z)-3,3-dimethyl-4-propyl-1,5-octadieneD) (Z)-5-propyl-3,9-decadiene

Aromatics

10.Identify the following as orthro-, meta-, or para- substituted.

A) ortho-B) meta-C) para-

11.What is the common name of the compound below?

A) phenolB) tolueneC) benzoic acidD) acetophenone

12.Select the correct IUPAC name for the compound below.

A) m-isopropylmethylbenzeneB) o-isopropylmethylbenzeneC) p-sec-propylmethylbenzeneD) m-sec-propylmethylbenzene

13.Which of the following is another accepted name for 1,2-dimethylbenzene?A) o-methyltolueneB) m-xyleneC) 3,4-dimethylbenzeneD) 1,2-diemthylcyclohexene

Oxidation/Reduction

14.Which of the following is the least oxidized?

A) AB) BC) CD) D

Degrees of Unsaturation

15.What is the degree of unsaturation for the following compound?C6H12O3A) 3B) 0C) 4D) 116.What is the degree of unsaturation for the following compound?C10H14N2A) 5B) 4C) 3D) 1Reactions: 2 points each

17.

A) AB) BC) CD) D

18.Which of the following will be the major product(s)?

A) AB) BC) CD) A and BE) A and C

19.

A) AB) BC) CD) DE) C and D

20.Indicate the major product.

A) AB) BC) CD) D

21.

A) AB) BC) CD) D

22.

A) AB) BC) CD) D

23.Which of the following reagents would be used to accomplish the following reactions?

A) Dess-Martin PeriodinaneB) CrO3

24.Which of the following reagents would be used to accomplish the following reactions?

A) Dess-Martin PeriodinaneB) CrO3

25.

A) AB) BC) CD) D

26.

A) AB) BC) CD) D

27.

A) AB) BC) CD) D

28.

A) AB) BC) CD) D

29.

A) AB) BC) CD) D

30.

A) AB) BC) CD) D

Synthesis: 2 points eachHow would you synthesize the following, assumng o, m, and p isomers can be isolated?

31.

A) EFCB) CEFC) FECD) ECF

32.

A) DMIB) DGIC) DIGD) DIM

Synthesis: 2 points

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

A) NOFB) NGC) ENGD) MG