UNIVERSITY OF TOLEDO

CHEM 2410 Organic Chemistry I

Examination No. III: Chapters 7 9 -- PRACTICE EXAM
Prof. J. Zubricky Spring 2012

Name: __________________________________

Total Points: ____ / 60 MC + _____ / 40 FR = _____ / 100

Section I. Multiple Choice.

Bubble the choice that best completes each phrase and/or answers the question on the Scantron sheet provided. Answers written in this section of the exam will not be graded (60 points). 1. 2. What form is this exam? a. Form A b. Form B c. Form C d. Form 1040EZ

Which atomic orbitals overlap to form the carbon-carbon triple bond of an alkyne? a. 2s + 2s; sp + sp; 2p + 2p b. sp + sp; sp + sp; 2p + 2p c. sp + sp; 2p + 2p; 2p + 2p d. sp2 + sp2; sp + sp; 2p + 2p What is the IUPAC name of the following compound?

3.

a. c. 4. 5.

(R)-4-methyl-2-hexyne (R)-3-methyl-4-hexyne

b. d. c.

(S)-4-methyl-2-hexyne (S)-3-methyl-4-hexyne 1-butyne d. 2-butyne

Which of the following has the lowest pKa? a. butane b. 1-butene

What is the major organic product obtained from the following reaction? a. c. (E) 1,2-dibromobutene (E) 2,3-dibromobutene b. d. (Z) 1,2-dibromobutene (Z) 2,3-dibromobutene

4.

What is the major organic product obtained from the following reaction?

a. 5.

2-hexanone

b.

hexanal

c.

2-hexanol

d.

cis-2-hexene

What is the best choice of reagent(s) to perform the following transformation?

a. c. 6.

H2/Lindlar catalyst (sia)2BH; followed by H2O2, NaOH

b. d.

Na/NH3 BH3; followed by H2O2, NaOH

Which of the following has the list of compounds in the correct order of decreasing boiling point (higher boiling point > lower boiling point)? a. 2-fluoropropane > 2-chloropropane > 2-bromopropane > 2-iodopropane b. 2-chloropropane > 2-iodopropane > 2-fluoropropane > 2-bromopropane c. 2-iodopropane > 2-chloropropane > 2-fluoropropane > 2-bromopropane d. 2-iodopropane > 2-bromopropane > 2-chloropropane > 2-fluoropropane

7.

What is the major organic product obtained from the following reaction?

a. 8.

b.

c.

d.

What is the correct order of stability of the following radicals (more stable > less stable)?

a. 9.

1>2>3

b.

2>1>3

c.

2>3>1

d.

3>2>1

What is the characteristic of a radical chain termination step? a. radicals are formed b. substitution products are formed c. a radical reacts with a molecule to give a new radical and a new molecule d. two radicals combine to give a molecule Which of the following is an accurate statement of Hammond's postulate? a. the transition state of an exothermic reaction will resemble the starting materials (reactants) more than the product b. the transition state of an exothermic reaction will resemble the products more than the starting materials (reactants) c. the transition state of an endothermic reaction will resemble the starting materials (reactants) more than the product d. the difference in energy between the starting materials (reactants) and transition state controls the rate of a reaction What is the major organic product obtained from the following reaction?

10.

11.

a. 12.

b.

c.

d.

The reaction of tert-butyl chloride, (CH3)3CCl, with water in an inert solvent gives tert-butyl alcohol, (CH3)3COH. What is the effect of doubling the concentration of water on the rate of the reaction? a. the rate remains the same b. the rate decreases by a factor of 2 c. the rate increases by a factor of 2 d. the rate increases by a factor of 4 Which of the following alkyl halides undergoes the fastest solvolysis reaction with methanol, CH3OH? a. methyl chloride b. ethyl chloride c. 2-chloropropane d. tert-butyl chloride

13.

14.

What is the major product formed upon treatment of (R) 1-bromo-4-methylhexane with sodium cyanide? a. (R) 1-cyano-4-methylhexane b. (S) 1-cyano-4-methylhexane c. (R) 4-methyl-1-hexene d. (S) 4-methyl-1-hexene Which of the following anions is the most nucleophilic in polar aprotic solvents? a. Fb. Clc. Brd. IWhat is the major organic product obtained from the following reaction?

15. 16.

a. 17.

b.

c.

d.

What is the best choice of reagent to perform the following transformation?

a. 18.

H2SO4

b.

H2O

c.

NaOCH3

d.

KOtBu

Which of the following represents the transition state of the rate-determining step in the reaction between 2-chloropropane and sodium amide leading to elimination?

a. 19.

b.

c.

d.

What is the major organic product obtained from the following reaction?

a. 20.

b.

c.

d.

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium methylthiolate, NaSMe? a. methyl iodide b. ethyl iodide c. 2-bromopropane d. tert-butyl chloride

Section II Free Response.

Write CLEARLY in complete sentences or SHOW ALL WORK if the problem calls for it. Remember to show all lone pair electrons if drawing a mechanism. On questions that do contain a choice of problems to answer, be sure to write SKIP on the problems you do not graded so that the TA will not grade the problem. If this is not done, only the first problems will be graded (40 points). 1. Mechanism. Show the mechanism by which the following reaction occurs. Be sure to show curved arrows to show the movement of electrons as well as all lone pair electrons. COMPLETE 2 OF 4 QUESTIONS. (20 points). a.

b.

c.

d.

2.

Synthesis. How do you prepare the following compounds? Be sure to show all reactants, reagents and intermediate products. COMPLETE 2 OF 4 QUESTIONS (20 points). a. 1-butyne from 1-butene

b.

prepare from bromocyclohexane

O H H O

c.

(CH3)2CHCH2OH from 2-methyl propene

d.

prepare from 1-bromo-1-methylcyclohexane

OH