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

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

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

The reaction proceeds via a carbocation intermediate

Q: Which of the following compounds is a tetrasubstituted alkene?

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

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

$\Delta G > 0$

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

$NH_2^- < OH^- < H_2O < NH_3$

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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