$$\displaystyle \begin{array}{c} \text{A six-membered ring with alternating single and double bonds} \\ \end{array}$$

$$\displaystyle \begin{array}{c} \text{An alkene with four different groups attached to the double bond} \end{array}$$

Question 1

Which of the following is a resonance structure of benzene ($$C_6H_6$$)?

Accepted Answer

$$\displaystyle \begin{array}{c} 	ext{A six-membered ring with alternating single and double bonds} \ \end{array}$$

Question 2

What is the hybridization of the carbon atom in carbon monoxide ($$CO$$)?

Accepted Answer

$$sp$$

Question 3

How many constitutional isomers exist for the molecular formula $$C_4H_{10}O$$?

Accepted Answer

7

Question 4

Which of the following carboxylic acids is the strongest acid?

Accepted Answer

$$ClCH_2CH_2COOH$$

Question 5

Which of the following compounds has the lowest boiling point?

Accepted Answer

$$CH_3CH_2CH_3$$

Question 6

Which of the following functional groups is NOT present in heroin (as shown in the exam)?

Accepted Answer

Aldehyde

Question 7

Which of the following compounds has the strongest intermolecular forces?

Accepted Answer

$$CH_3CH_2OH$$

Question 8

What is the IUPAC name of the hydrocarbon $$CH_3CH_2CH_2CH_2CH_3$$?

Accepted Answer

Pentane

Question 9

How are the following two compounds related?

$$\displaystyle \begin{array}{c} 	ext{(CH}_3)_2CHCH_2CH_3 	ext{ and } CH_3CH_2CH_2CH(CH_3$)_2 \end{array}$$

Accepted Answer

Constitutional isomers

Question 10

If a 50:50 mixture of two enantiomers is lost at a rate of 50%, what is the ratio of the two enantiomers?

Accepted Answer

1:1

Question 11

Which of the following values does NOT favor the products of a chemical reaction at equilibrium?

Accepted Answer

$$\Delta G \u003e 0$$

Question 12

Which of the following bonds has the highest bond dissociation energy?

Accepted Answer

$$C \equiv C$$

Question 13

Which nucleophilic substitution is the fastest? (DMSO = dimethylsulfoxide, $$CH_3OH = $$methanol)

Accepted Answer

$$CH_3CH_2Br in $$DMSO

Question 14

Rank the following in order of increasing leaving group ability, putting the worst leaving group first: $$OH^-, NH_2$^-, H_2O, NH_3$

Accepted Answer

$$NH_2$$^- \u003c OH^- \u003c H_2O \u003c $$NH_3$$

Question 15

Which of the following statements is NOT true for the E2 reaction mechanism?

Accepted Answer

The reaction proceeds via a carbocation intermediate

Question 16

What is the major product of the following E2 elimination?

$$\displaystyle \begin{array}{c} 	ext{2-bromopentane + strong base} \end{array}$$

Accepted Answer

Trans-2-pentene

Question 17

What is the major product when 1-butyne is treated with $$H_2O$$ and $$H_2SO_4 in $$the presence of $$HgSO_4$$?

Accepted Answer

Butan-2-one

Question 18

How many of the following compounds have five degrees of unsaturation?

$$\displaystyle \begin{array}{cccc} 	ext{Benzene} & 	ext{Cyclopentadiene} & 	ext{Naphthalene} & 	ext{Cyclohexene} \end{array}$$

Accepted Answer

2 compounds

Question 19

Which of the following compounds is a tetrasubstituted alkene?

Accepted Answer

$$\displaystyle \begin{array}{c} 	ext{An alkene with four different groups attached to the double bond} \end{array}$$

Organic Chemistry Final Exam Study Guide: Key Concepts and Practice

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