Chapter 12 1. What is the electrophile in the Friedel-Crafts alkylation reaction below?

A) AlCl3

B) Cl

C) benzene

D) (CH3)3C+

2. Which species below best depicts the electrophile in the FeBr3-catalyzed bromination of benzene? A) Br2 B) FeBr4C) D) FeBr3

3. Which point on the potential energy diagram corresponds to the species shown to the right for the electrophilic nitration of benzene with HNO3/H2SO4?

A) A B) B

C) C

D) D

4. How many mononitration products are possible in the nitration of naphthalene, shown below?

A) only 1

B) 2

C) 3

D) 4

5. Which of the following groups are ortho/para directors? I. NO2 II. OCH3 III. CO2CH3 IV. CH3 A) I and III B) II and III C) II and IV D) III and IV

6. Which of the following is the best method to make n-butylbenzene?

A) A B) B

C) C

D) D

7. Based on resonance theory, what is the approximate charge on the indicated carbon?

A) +1

B) +0.50

C) +0.33

D) +0.20

8. Which of the following is the best method to make meta-bromoethylbenzene from benzene?

A) A B) B

C) C

D) D

9. Nitration of chlorobenzene has a reaction rate which is __________ than the nitration rate of benzene and gives primarily the _____________ product(s). A) faster, ortho/para B) faster, meta C) slower, ortho/para D) slower, meta

10. Where would the compound shown below undergo bromination with Br 2/FeBr3?

A) B)

ortho/para position on ring 1 meta position on ring 1

C) D)

ortho/para position on ring 2 meta position on ring 2

Chapter 13 11. Which of the following gives the furthest downfield shift from TMS in its proton NMR spectrum? A) CCl4 B) CHCl3 C) CH2Cl2 D) CH3Cl

12. How many different sets of equivalent protons are there for para-xylene (1,4-dimethylbenzene)? A) only 1 B) two C) three D) four

13. How many different sets of equivalent protons are there in the following compound?

A) three

B) four

C) five

D) six

14. Which compound below fits the following proton NMR data? triplet singlet quartet 1.22 (3H) 1.98 (3H) 4.07 (2H)

A) A B) B

C) C

D) D

15. The proton NMR of a compound, C8H9ClO, has the following peaks. Which compound below best fits the data? broad singlet triplet triplet doublet doublet A) I B) II C) III 2.41 (1H) 2.41 (2H) 3.69 (2H) 7.02 (2H) 7.50 (2H) D) IV

16. A triplet and quartet pattern in 1H NMR often indicates the presence of a(n) A) ethyl group. B) propyl group. C) isopropyl group. D) phenyl group.

17. Identify the C4H9Cl isomer given the following proton NMR data: doublet multiplet doublet 1.04 (6H) 1.95 (1H) 3.35 (2H)

A) A B) B

C) C

D) D

18. What is the multiplicity of the indicated carbon in an off-resonance decoupled C-13 NMR spectrum? (In off-resonance decoupled spectra, direct 13C-1H coupling is observed.)

A) singlet

B) doublet

C) quartet

D) multiplet

19. A C-13 NMR spectrum of a compound, C10H14, has five peaks. Two peaks are in the 10-30 ppm region and the other three are in the 120-140 ppm area. Which of the following compounds fits the data?

A) I

B) II

C) III

D) IV

20. Which of the compounds below would exhibit the FEWEST peaks in the 13C NMR spectrum?

A) A B) B

C) C

D) D

Chapter 14 21. The reaction of a Grignard reagent with an aldehyde followed by dilute acid gives a(n) A) primary alcohol. B) secondary alcohol. C) tertiary alcohol. D) ester.

22. Select the strongest base in the following. A) NaNH2 B) CH3Li C) NaOCH2CH3

D) HCCNa

23. Which of the following reaction sequences would convert 2-butanol into the deuterated compound below?

A) A B) B

C) C

D) D

24. What is the major product of the following reaction?

A) B)

2-ethyl-1-pentanol 2-ethyl-1-butanol

C) D)

3-pentanol 3-methyl-1-pentanol

25. Which of the following pairs of reagents would you use to prepare 4-methyl-2-pentanol?

A) A B) B

C) C

D) D

26. What is the product of the following reaction?

A) A

B) B

C) C

D) D

27. Which of the following are intermediates in the reaction of excess methylmagnesium bromide with ethyl benzoate (shown below) to make 2-phenyl-2-propanol?

A) B) C) D)

I and II I and III II and III I, II, and III (they are all intermediates)

28. What is the product of the reaction shown below?

A) 4-nonene

B) nonane

C) 4-bromononane

D) 5-bromononane

29. Which of the following are intermediates in the reaction below?

A) A B) B

C) C

D) D

30. How many stereoisomers are formed in this reaction?

A) just one

B) two

C) three

D) four