Periodic Table of the Elements

1 2

H
5 6 7 8

H
1.00794 9

He
4.002602 10

1.00794

Li
10.811 13 14 15 12.0107

Be Al
26.981538 28.0855 30.973761

B Si P

O
16 32.066

F
17

Ne
18.9984032 20.1797 18

6.941

9.012182

14.00674 15.9994

11

12

Na Mg Ti
50.9415 41 42 48 43 44 45 46 47 49 51.9961 54.938049 55.845 58.933200 58.6934 63.546 65.39 69.723 40 22

S
74.92160

Cl
35.4527

Ar
39.948

22.989770 24.3050

19

39.0983

K Nb
92.90638 73 74 183.84 192.217 109 110 (269) 111 (272) 106 107 108 75 78 195.078 80 200.59 112 (277) 186.207 76 190.23 102.90550 77 79 196.96655 95.94 (98) 106.42 107.8682 112.411 101.07

Ca V Mo Rh Ir Pt Au Hg Pd Ag W Os Mt
(266)

20 23

40.078

Sc Tc Re Hs
(265)

21

Cr Ru Cd In
114.818 81 204.3833

24

Mn

25

Fe

26

Co

27

Ni

28

Cu

29

Zn

30

Ga

31 32

44.955910

47.867

72.61

Ge
50

As Sn
118.710 82

33

34 78.96 51 52

Se Sb
121.760 83

Br
79.904 53

35

83.80

Kr
54

36

37

38

39

Rb
72

Sr Ta
180.9479 105

Zr

Te
127.60 84

I Tl
207.2

Xe
126.90447 131.29 85 86

85.4678

87.62

88.90585

91.224

55

56

57

132.90545 137.327 104

Cs Db
(262) (263) (262)

Ba Sg Bh

138.9055

La

178.49

Hf

Pb
114 (289) (287)

208.98038

Bi

(209) 116 (289)

Po

(210)

At

Rn
(222) 118 (293)

87

88

89

(223)

Fr

Ra

(226)

Ac

(227)

Rf

(261)

58 140.116 140.90765 144.24 92 93 90 232.0381 231.03588 238.0289 91

59

60

61 (145)

62 150.36

63 151.964 94 95

64 157.25 96

65

66

67

68

69

70

71

Ce U Np
(237)

Pr

Nd

Pm Sm Eu
(244)

Gd
(243)

158.92534 97

Tb Pu Am Cm
(247)

162.50 98

Dy Bk
(247)

164.93032 167.26 99 (251) 100

Ho Cf

Er

168.93421 173.04 101 (252) 102

Tm Es Fm
(257)

Yb

174.967 103

Lu Md No
(258) (259)

Th

Pa

(262)

Lr

S.E. Van Bramer, 7/22/99 1995 IUPAC masses and Approved Names from http://www.chem.qmw.ac.uk/iupac/AtWt/ masses for 107-111 from C&EN, March 13, 1995, P 35 112 from http://www.gsi.de/z112e.html 114 from C&EN July 19, 1999 116 and 118 from http://www.lbl.gov/Science-Articles/Archive/elements-116-118.html

Name: CHEM 3053: Exam 3

NOTE: ! ! ! Bubble in Your Name (Last, space, First) Bubble in Your ID# Bubble in Special Code 100031

1. Predict the sign of !S of the following reaction?

N

N3

N N

! ! !

A)! positive B)! negative C)! no change

2. Which of the following cannot be a electrophile?

A. B. Br C. O D. Br

3. For the following reaction step, indicate which pattern it belongs to.
H

! C)! Nucleophilic Attack D)! Rearrangement

! !

A)! Proton Transfer! B)! Loss of Leaving Group!

4. Which of the following is the product of the following reaction?

Br
N3 A. H 2N B.

NaN3

N3 C.

H 2N D.

5. Rank the following substrates from most to least reactive in an SN1 reaction.
I I A. B. C. I D. I

A) B) C) D)

A>B>C>D A>B>D>C D>A>B>C D>C>B>A

E) F) G) H)

B>C>D>A B>D>A>C C>B>A>D D>A>B>C

6.! Identify the sequence of steps in the following reaction.

H Cl

Cl

Cl

! ! A)! Proton transfer, Proton transfer! D)! Nucleophilic attack, Proton transfer ! B)! Proton transfer, Loss of leaving group! E)! Proton transfer, Nucleophilic attack ! C)! Loss of leaving group, Nucleophilic Attack! F)! Nucleophilic Attack, Nucleophilic Attack 7. Given the following rate law, what will happen to the rate if the concentration of both reactants is doubled? Rate = k[Me3N][MeI] A) It will be doubled. B) It will not change. C) It will decrease in half. D) It will increase 4-fold.

8. Which of the following is not a possible step in a substitution reaction?

A. Br CN CN Br B. OH OH2

C. Br Br D. Br Br Br Br

9. Which of the following is the major product for the following SN1 reaction?
Br H2O

OH OH A. B.

HO
C. D.

OH2

10. Which reagents would best accomplish the following reaction?

Br HS

A) H2S in water B) H2S in DMSO C) NaSH in water

D) NaSH in DMSO E) H3S+ in water F) H3S+ in DMSO

11. Which of the following sets of reagents would best accomplish the following transformation?
OH A. HBr B. D. Br NaBr

C.

SO2Cl pyridine

SO2Cl pyridine then NaBr

12.!Which of the following is the correct IUPAC name for the following compound?

! !

A)! 1-methyl-2-cyclohexene! B)! 2-methylcyclohexene!

C)! 3-methylcyclohexene D)! 1-methyl-5-cyclohexene

13.!Rank the following from most to least stable.

A.

B.

C.

! ! !

A)! A, B, C! B)! C, B, A! C)! B, C, A!

D)! B, A, C E)! A, C, B F)! C, A, B

14. Which of the following shows the rst step for a stepwise elimination.

H A. Br OMe H B. Br OMe

C. OMe

H OMe

D. H OMe

15. Which of the following is the major product of the following reaction?
O Cl A. B. C.

16.!Which of the following is the structure of the rearranged carbocation in the following ! dehydration?
OH H2SO4

A.

B.

C.

D.

17.!By what mechanism is the following reaction likely to occur?

I N N

! ! ! ! A)! SN1! B)! SN2! C)! E1! D)! E2 E)! SN2 and E2 F)! SN1 and E1

18.!What is the most likely product for the following reaction?

OTs H2O

!
OH OH

! ! ! ! !

! I! A)! I! B)! II! C)! III! II!

! III D)! I and II E)! I and III F)! I, II, and III

19.!By what mechanism is the following reaction likely to occur?

Br NaSH

! ! ! ! A)! SN1! B)! SN2! C)! E1! D)! E2 E)! SN2 and E2 F)! SN1 and E1

20. In an addition reaction to an alkene, the ! bond plays the role of: A) nucleophile B) electrophile C) leaving group D) A and B E) B and C

21. The regioselectivity and stereospecificity in the hydroboration-oxidation of an alkene is best described as: A) B) C) D) E) Markovnikov orientation with syn-addition Markovnikov orientation with anti-addition Anti-Markovnikov orientation with syn-addition Anti-Markovnikov orientation with anti-addition Markovnikov orientation with both syn- and anti-addition

22. The expected major product of the following reaction is:

HBr ?

A)
Br

D)
Br

B)
Br

E)
Br Br

C)
Br

23. What is the expected major product for the following reaction?
MeOH [H2SO4]

A)

D)
+ enantiomer
OMe

OMe

B)
+ enantiomer OMe

E)
OMe + enantiomer

C)
OMe + enantiomer

24. Which of the following reagents accomplishes the transformation shown below?
?

A) H2/HCl B) H2/H2SO4 C) H2/Ni 25.

D) H2O/Ni E) H2O/H2SO4

What major product is expected from the following reaction?

Br2 H2O OH Br Br OH OH I II III IV Br V Br Br OH Br ?

A) B) C) D) E)

I II III IV V

F) G) H) I) J)

I and II I and III II and IV III and IV III, IV, and V