1

CBENISTRY 4u SECTI0NS A anu W

TBIRB EXAN
Naich 27, 2u14
Name:_________________KEY___________________________
Section:___________
Stuuent numbei:________________________________

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567 )'38

1. The C-C bonu length in benzene is:
A. aveiage of C-C single anu uouble bonus C. the same as a C-C single bonu
B. the same as a C-C uouble bonu in alkene B. not measuiable

2. Which of the following molecules has the highest bp.
A. C.
B. B.

S. Which haliue will unueigo an S!2 ieaction the fastest.
A. C.
B. B.

4. Which of the following conuitions will N0T make an acetal fiom this staiting
mateiial.


A. Na0B, excess Ne0B C. cat. B2S04, excess Ne0B
B. "-TSA, ethylene glycol B. cat. BCl, excess Et0B

S. Which staiieu caibon (*C) has the highest oxiuation numbei.
A. C.
B. B.

I. ________
II. 1. ______
2. ______
S. ______
4. ______
S. ______
B0N0S _____
T0TAL:
2
6. Which compounu contains the N0ST aciuic (Binsteu aciu) hyuiogen.
A. C.
B. B.

7. Which solvent will you use to conuuct the tiansfoimation below.


A. CBS0B C. BNS0
B. BNF B. B20

8. Which of the following ieagents will N0T conveit a piimaiy alcohol into a goou
leaving gioup.
A. NaB C. thionyl chloiiue
B. "-toluenesulfonyl chloiiue B. PBiS

9. Which of the following compounus will unueigo nitiation of the aiomatic iing the
fastest.
A. C.
B. B.

1u. Which of the following conuitions will favoi an S!1 ieaction foi this substiate.

A. Ethanol C. NaCNBNS0
B. Na0EtEt0B, heat B. K0
#
Bu
#
Bu0B, heat





S
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1. 0nuei each staiting mateiial anu type of ieaction, choose among the following:
!"#!$%&$'( !*+,'-$( #&!'( -".+'*/01+'( 2!3%( 2!4( 2!5( 64( 65. If it is a substiate,
.1%.+' $0' +'&,1-7 7%*"/ *% 80&$ 81++ #' $0' +'&,1-7 7%*"/ in it. (2u pts)


A.
Type of ieaction.

B.
Type of ieaction.

C.
Type of ieaction.


B.
Type of ieaction.

E.
Type of ieaction.


2. Rank the following compounus in teims of aciuity of the hyuioxyl - B, with 1
being the N0ST aciuic, anu 4, the LEAST aciuic: (8 pts)




1 2 S 4
4
S. Biaw the staiting caibonyl compounu (ie aluehyue oi ketone) fiom each of these
acetals: (12 pts)




























4. Wiite whethei the following compounus aie aiomatic oi not aiomatic. (S pts)












not aiomatic
aiomatic
aiomatic not aiomatic
not aiomatic
S
S. Pioviue the missing infoimation in the schemes below. Inuicate steieochemistiy
wheie applicable. (SS pts)
A.

























+
2. uilute aciu
1.
6

B.





























1.
2.
1. LAB
Aciu
0i BS0
+
PBiS
Ng, ethei
(Swein oxiuation)
7
C.













B0N0S. Biaw the stiuctuie of the staiting caibonyl compounu foi the acetal below.
(S pts)








BN0S , B2S04