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7/25/2019 ch13 problems
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Chapter Thirteen
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.2
1. Which fee adical !o"ld be #ost stable$
A)
%)
C)
&)
')Ans: %
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.2
2. Which fee adical !o"ld be least stable$
A)
%)
C)
&)
')
Ans: &
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Topic: Stability (Alkenes, Cations, Radicals) Section: 13.2
3. Which fee adical !o"ld be #ost stable$
A)
C H 3C C C H 2
C H 3
%)
C C H 2C H 2
C H 3
C H 2
C)
C H 3C C H 2C H 3
C H 3
&)
C H 2C H C C H 2
C H 3
')
C H 3 C H C H C H 3
C H 3
Ans: A
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.2
. Which fee adical !o"ld be #ost stable$
**
A) %)
C)
&) *') *
Ans: C
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Topic: Stability (Alkenes, Cations, Radicals) Section: 13.2
+. Which fee adical !o"ld be least stable$
**
A)
%)
C) &) *
') *
Ans: '
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.2
.
Which hydo-en ato#(s) of
C H C HC HC H 3 C H
C H 3
C H C H 3
) ) ) ) ) ) ) *
*
isae #ost
s"sceptible to abstaction by fee adicals$
A) %)
C)
&) *') *
Ans: &
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.2
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/.
Which hydo-en ato#(s) of
*
*
isae #ost s"sceptible to abstactionby fee adicals$
A) %)
C)
&) *') *
Ans: %
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.2
0.
Which hydo-en ato#(s) of
*
*
isae least s"sceptible to
abstaction by fee adicals$
A)
%) C)
&) *') *
Ans: C
Topic: Allylic alo-enation Section: 13.2
. Which set of conditions does not es"lt in allylic halo-enation of an alkene$
A) Cl2at C
%) Cl2in CClat 2+C
C) Cl2, R44R,h&) % 2at lo! concentation in CCl') 56%o#os"ccini#ide in CCl, R44R
Ans: %
Topic: Allylic alo-enation Section: 13.2
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1.
Which cabon of
C H 3 C H C H 2 C H C H 2
C H 3
* ) * ) ) ) ) ) ) is pedicted to be the #a7o site of
s"bstit"tion !hen this alkene eacts !ith chloine at C$
A) %)
C)
&) *') *
Ans: C
Topic: 8"ltistep Reactions Section: 13.2
11. Which !o"ld be the best synthesis$
C H 2 C H C H 3
$C H 2 C H C H 2C l
B r B r
A)9 o p e n e
% 2 , C C l ( C l 2 , h
%)9 o p e n e
C l 2 , ( 3 3o C % 2 , C C l (
C) % 2 , h 9 o p e n e
1 C l
&)9 o p e n e
C l 2 , C C l (5 % S , C C l (
')9 o p e n e
C l 2 , C C l ( 5 % S , C C l (
Ans: %
Topic: Allylic alo-enation Section: 13.2 and chapte 1
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12. Which of the follo!in- co#po"nds is not fo#ed as a es"lt of a chain6te#ination stepin the fee adical chloination of popene$
A) C2CC2Cl
%) Cl2C) C2CC2C2CC2&) Cl
') All can be fo#ed in chain6te#ination steps.
Ans: &
Topic: 8olec"la 4bitals Section: 13.3
13. The allyl adical has ho! #any bondin- #olec"la obitals$
A) 1
%) 2C) 3
&)
') +Ans: A
Topic: 8olec"la 4bitals Section: 13.3
1. The allyl adical has ho! #any electons in bondin- #olec"la obitals$
A) 1
%) 2
C) 3&)
') +
Ans: %
Topic: 8olec"la 4bitals Section: 13.3
1+. The allyl adical has ho! #any electons in non6bondin- #olec"la obitals$
A) 1
%) 2
C) 3&)
') +
Ans: A
Topic: 8olec"la 4bitals Section: 13.3
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1. The allyl adical has ho! #any #olec"la obitals$
A) 1
%) 2
C) 3&)
') +
Ans: C
Topic: 8olec"la 4bitals Section: 13.3
1/. The 484 of the allylic adical has ho! #any electons in its -o"nd state$A) 1
%) 2
C) 3&)
')
Ans: A
Topic: 8olec"la 4bitals Section: 13.3
10. The ;
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2. What pod"ct(s) !o"ld yo" e=pect fo# the follo!in- s"bstit"tion eaction of 1C6labeled popene$
C2:C6C31
lo! conc. Cl2
+oC
A) 1C2C>C2Cl alone%) 1C2C>C2Cl and C2C>
1C2Cl, in e?"al a#o"ntsC) C2C>
1C2Cl alone
&) #oe1C2CC2Cl, b"t a little C2C>1C2Cl
') #oe C2C>1C2Cl, b"t a little
1C2CC2ClAns: %
Topic: Allylic S"bstit"tion Section: 13.3
21. What pod"ct(s) !o"ld yo" e=pect fo# the follo!in- s"bstit"tion eaction of 1C6
labeled popene$
lo! conc. Cl2
+oC13
A) 13C2C>C2Cl alone%) 13C2C>C2Cl and C2C>
13C2Cl, in e?"al a#o"nts
C) C2C>13C2Cl alone
&) #oe13C2CC2Cl, b"t a little C2C>13C2Cl
') #oe C2C>13C2Cl, b"t a little
13C2CC2Cl
Ans: %
Topic: Allylic S"bstit"tion Section: 13.3
22. What pod"ct(s) !o"ld yo" e=pect fo# the follo!in- s"bstit"tion eaction$
Cl
ClCl
Cl
*
@ @ @ @
Cl2
+oC
@$
A)
%)
C) &) *
') 8oe than one of the aboe
Ans: '
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Topic: Allylic alo-enation Section: 13.2 and 13.3
23. What is (ae) the pod"ct(s) of the follo!in- eaction$
ClCl
Cl
Cl2
oC
$
A)
%) C)
&) a #i=t"e of and
') a #i=t"e of and Ans: '
Topic: Allylic alo-enation Section: 13.2 and 13.32. An "nsat"ated pod"ct es"lts fo# the eaction of cyclohe=ene !ith !hich of these$
A) %2CClat 2+C
%) 5%SCCl, R44R
C) Cl, R44R&) Cl, no peo=ides
') 8oe than one of these
Ans: %
Topic: Allylic alo-enation Section: 13.2 and 13.3
2+. What pod"ct(s) !o"ld yo" e=pect fo# the follo!in- s"bstit"tion eaction of 1C6labeled popene$
1 4 C H 2 C H C H 3
5 6 b o # o s " c c i n i # i d e
R 4 4 R , C C l (
$
A) 1C2C>C2% alone%) 1C2C>C2% and C2C>
1C2% in e?"al a#o"nts
C) C2C>1C2% alone
&) 8oe 1C2CC2% b"t a little C2C>1C2%
') 8oe C2C1
C2% b"t a little1
C2CC2%Ans: %
Topic: Allylic alo-enation Section: 13.2 and 13.3
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2. Teat#ent of 26b"tene (ciso trans) !ith Cl2at C !o"ld yield #ainly:
A) C2ClCClC2C3%) C3CClC2C3C) C3CCClC3&) C3CCC2Cl and C3CClCC2') C3CClCClC3
Ans: &
Topic: Synthesis of Allylic alides Section: 13.2 and 13.3
2/. Teat#ent of 26b"tene (ciso trans) !ith 56bo#os"ccini#ide in CCl!o"ld yield
#ainly:
A) C3C%C%C3alone%) C3CC%C3alone
C) C3CCC2% alone
&) C2%C2CC2and C3CCC2%') C3C%CC2and C3CCC2%
Ans: '
Topic: Synthesis of Allylic alides Section: 13.2 and 13.3
20. Teat#ent of 6#ethylcyclohe=ene !ith 56bo#os"ccini#ide in CCl!o"ld yield
#ainly:Br
Br Br
Br
*A)
%) C)
&) *
') All of the aboe
Ans: '
Topic: Synthesis of Allylic alides Section: 13.2, 13.3 and peio"s chaptes
2. Which of the follo!in- co"ld be "sed to synthesiBe 36bo#opopene$
A)C H 3C H C H 2 % 2
2 + o C
C C l (%)
C H 3C H C H 2 5 6 b o # o s " c c i n i # i d eC C l (
R 4 4 R
C) C2CC24 9%3
&) 8oe than one of these
') 5one of theseAns: & (%C)
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Topic: Synthesis of Allylic alides Section: 13.2, 13.3 and peio"s chaptes
3. Which of the follo!in- co"ld be "sed to synthesiBe 36bo#ocyclopentene$
A) Cyclopentene %2, CCl, 2+o
%) Cyclopentene 5%S, CCl(R44R)
C) 36Cyclopentenol 9%3
&) %oth A) and %)
') %oth %) and C)Ans: '
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.
31. Which cabocation !o"ld be least stable$
* *
A) %)
C)
&) *') *
Ans: '
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.32. Which cabocation !o"ld be #ost stable$
A)
%)
C)
&)
')
Ans: C
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.
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33. Which cabocation !o"ld be least stable$
A)
%)
C)
&)
')
Ans: &
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.
3. Which cabocation !o"ld be #ost stable$
) ) ) ) ) ) ) * *
C H 2 C H 3 C H 3 C H 3 C H 3
A) %)
C)
&) *') *
Ans: C
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.
3+. Which cabocation !o"ld be #ost stable$
* *
A)
%) C)
&) *
') *Ans: C
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Topic: Stability (Alkenes, Cations, Radicals) Section: 13.
3. Aan-e these cabocations in ode of e=pected inceasin- stability.
* *
A) * D D D * D
%) *DDD*DC) * DD D*D
&) * D D D D *
') D D * D D *
Ans: %
Topic: 8olec"la 4bitals Section: 13.
3/. The allyl cation has ho! #any electons in bondin- #olec"la obitals$
A) 1
%) 2C) 3
&)
') +Ans: %
Topic: 8olec"la 4bitals Section: 13.
30. The allyl cation has ho! #any bondin- #olec"la obitals$
A) 1%) 2
C) 3
&) ') +
Ans: A
Topic: 8olec"la 4bitals Section: 13.
3. The allyl cation has ho! #any #olec"la obitals$A) 1
%) 2C) 3
&)
') +Ans: C
Topic: Resonance Section: 13.+
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. Which is not an e=a#ple of esonance$
*
CH2
CH2
CH2=CHCH2
CH2=CHCHCH2CCl3
CH2
CH3
CH2CH=CH2
CH2CH=CHCH2CCl3
. .
. .
A) %)
C)
&) *') 5one of these ae e=a#ples of esonance.
Ans: C
Topic: Resonance Section: 13.+
1. Which is not a pope esonance st"ct"e fo 1,36b"tadiene$
A) C2C>CC2%)
C H C H 2C HC H 2
C)C H C H 2C HC H 2
&)C HC H 2 C H C H 2
') All ae coect
Ans: %
Topic: Resonance Section: 13.+
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2. Which pai does not epesent a pai of esonance st"ct"es$
)
) )
) ) )
) *
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
C H 2 C H 2
C H 2 C H 3
a n d
a n d
a n d
a n d
A)
%) C)
&) *') All of these epesent pais of esonance st"ct"es.
Ans: &
Topic: Resonance Section: 13.+
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3. Which pai does not epesent a pai of esonance st"ct"es$
and
and
and
and
*
A)
%) C)
&) *
') All of these epesent pais of esonance st"ct"es.Ans: &
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Topic: Resonance Section: 13.+
. Which pai does not epesent a pai of esonance st"ct"es$
and
and
and
and
*
A) %)
C)
&) *') All of these epesent pais of esonance st"ct"es.
Ans: '
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Topic: Resonance Section: 13.+
+. Which pai does not epesent a pai of esonance st"ct"es$
and
and
and
and
*
A) %)
C)
&) *') All of these epesent pais of esonance st"ct"es.
Ans: '
Topic: Alkene Classification Section: 13.
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. Select the st"ct"e of the con7"-ated diene.
) ) ) ) ) ) ) * *
A) %)
C)
&) *') *
Ans: %
Topic: Alkene Classification Section: 13.
/. Select the st"ct"e of the con7"-ated diene.
* *
A)
%) C)
&) *
') *
Ans: C
Topic: Alkene Classification Section: 13.
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0. Select the st"ct"e of the con7"-ated diene.
* *
A) %)
C)
&) *
') *Ans: C
Topic: Alkene Classification Section: 13.
. Select the st"ct"e of the isolated diene.
* *
A) %)
C)
&) *
') *Ans: &
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Topic: Alkene Classification Section: 13.
+. Select the st"ct"e(s) of the con7"-ated diene(s).
* *
A) and
%) and C) and *
&) , and *
') *
Ans: C
Topic: Alkene Classification Section: 13.
+1. Which of the follo!in- dienes is a c"#"lated diene$
A) C2CC2C2CC2%) C2CCCC2C3C) C3CCCC2C3&) C3CCCCC3') C3CCC2CC2
Ans: C
Topic: Alkene Classification Section: 13.
+2. Which of the follo!in- dienes is a c"#"lated diene$
A) C2CC2C2C2CC2%) C2CCCC2C2C3C) C3CCCC2C2C3&) C3CCCCC2C3') C3C2CCC2CC2
Ans: C
Topic: Alkene Classification Section: 13.
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+3. Select the st"ct"e(s) of the con7"-ated diene(s).
O O
* *
A) and
%) and
C) and *&) , and *
') *
Ans: %
Topic: 5o#enclat"e Section: .+, . and 13.+.
What is an
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+. What is an 2,,>5onatiene
%) (2E,',E)>2,,>5onatiene
C) (2',E,E)>2,,>5onatiene&) (3E,+E,/')>3,+,/>5onatiene') (3E,+',/')>3,+,/>5onatiene
Ans: C
Topic: 5o#enclat"e Section: .+, ., /.2 and 13.
+/. What is an 3,,/,0>teta#ethyl62,,>5onatiene
%) (2E,',')>3,,/,0>teta#ethyl62,,>5onatieneC) (2',E,')>2,3,,/>teta#ethyl63,+,/>5onatiene
&) (2',E,')> 2,3,,/>teta#ethyl63,+,/>5onatiene
') (2',',')>3,,/,0>teta#ethyl62,,>5onatieneAns: '
Topic: %ond ;en-ths Section: 13./
+0. Which co#po"nd !o"ld hae the shotest cabon6cabon sin-le bond$A) C3>C3%) C2C>C3C) CC>CC
&) C2C>CC
') C2C>CC2Ans: C
Topic: %ond ;en-ths Section: 13./
+. Which co#po"nd !o"ld hae the shotest cabon6cabon sin-le bond$
A) CC>CC>C2>C3%) C2C>CC>C3C) CC>C2>CC>C3
&) C2C>CC>C2>C3') C3>CC>CC>C3
Ans: '
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Topic: %ond ;en-ths Section: 13./
. Which cabon6cabon bond in the follo!in- co#po"nd !o"ld yo" e=pect to be shotest$C C CHH CH2 CH3CH
* *A) %)
C)
&) *
') *Ans: A
Topic: %ond ;en-ths Section: 13./
1. Which cabon6cabon bond in the follo!in- co#po"nd !o"ld yo" e=pect to be lon-est$
C C CHH CH2 CH3CH
* *A)
%)
C) &) *
') *
Ans: '
Topic: 8olec"la 4bitals Section: 13./
2. 1,369entadiene has ho! #any bondin- #olec"la obitals$
A) 1
%) 2
C) 3&)
')
Ans: %
Topic: 8olec"la 4bitals Section: 13./
3. 1,36b"tadiene has ho! #any bondin- #olec"la obitals$
A) 1
%) 2
C) 3&)
')
Ans: %
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Topic: 8olec"la 4bitals Section: 13./
. 1,369entadiene has ho! #any antibondin- #olec"la obitals$
A) 1
%) 2C) 3
&)
') Ans: %
Topic: 8olec"la 4bitals Section: 13./
+. 1,36b"tadiene has ho! #any electons in its -o"nd state bondin- #olec"la obitals$
A) 1
%) 2
C) 3&)
') Ans: &
Topic: 8olec"la 4bitals Section: 13./
. 1,36b"tadiene has ho! #any electons in its -o"nd state antibondin- #olec"la
obitals$
A) 1%) 2
C) 3
&) ')
Ans: '
Topic: 8olec"la 4bitals Section: 13./
/. The 484 of 1,36pentadiene has ho! #any electons in its -o"nd state$
A) 1%) 2
C) 3
&) ')
Ans: %
Topic: 8olec"la 4bitals Section: 13./
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0. The ;
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/3. Which of the follo!in- co#po"nds !o"ld be the #ost stable$
) ) ) ) ) ) ) *
A)
%) C)
&) *
') They ae all of e?"al stability.Ans: A
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.0
/. Which diene !o"ld be least stable$
) ) ) ) ) ) ) * *
A)
%) C)
&) *
') *Ans: C
Topic: eat of ydo-enation Section: 13.0
/+. Which alkene !o"ld yo" e=pect to hae the hi-hest heat of hydo-enation$
A)
%)
C)
&)
')
Ans: A
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.0
/. Which of the follo!in- dienes !o"ld yo" e=pect to be the #ost stable$
A) C3C2CCC2CCC3%) C3CCCCC2C3C) C2CC2C2C2CC2&) C2CCCC2C2C3') C3CC(C3)CCC2C3
Ans: '
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Topic: Stability (Alkenes, Cations, Radicals) Section: 13.0
0. Which alkene !o"ld yo" e=pect to be #ost stable$
A) C2CC2C2CC2%)
C C
H
C H 3H
C H C H 2C H 2
C)
C C
C H 3 C H 2C H
H H
C H 2
&)
C C
C
HH
C H 3 C
H
C H 3
H
')
C C
C H 3
H C
H
C
H
H
C H 3
Ans: '
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.0
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01. Aan-e these he=adienes in ode of e=pected deceasin- stability.
* *
A) * F F F F *%) F * F F F *
C) * F F F * F
&) * F F F F *') F F * F F *
Ans: &
Topic: Stability (Alkenes, Cations, Radicals) Section: 13.0
02. Aan-e these he=adienes in ode of e=pected inceasin- stability.
* *
A) * D D D D *
%) D * D D D *
C) * D D D * D &) * D D D D *
') D D * D D *
Ans: A
Topic: eat of ydo-enation Section: 13.0
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03. Which alkene !o"ld yo" e=pect to hae the s#allest heat of hydo-enation$A) C2CC2C2CC2%)
C C
H
C H 3H
C H C H 2C H 2
C)
C C
C H 3 C H 2C H
H H
C H 2
&)
C C
C
HH
C H 3 C
H
C H 3
H
')
C C
C H 3
H C
H
C
H
H
C H 3
Ans: '
Topic: eat of ydo-enation Section: 13.0
0. Which alkene !o"ld yo" e=pect to hae the s#allest heat of hydo-enation$
A)
%)
C)
&)
')Ans: '
Topic: eat of ydo-enation Section: 13.0
0+. Which alkene !o"ld yo" e=pect to hae the lo!est heat of hydo-enation$
* *
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A) %)
C)
&) *') *
Ans: A
Topic: eat of ydo-enation Section: 13.0
0. 'sti#ate the stabiliBation ene-y fo 1,36b"tadiene "sin- the heats of hydo-enation in
Table 1.
Table 1. eats of ydo-enation fo Selected Co#po"nds
Co#po"nd 8oles 2 (kG #ol61)
16%"tene 1 612/
169entene 1 612
1,36%"tadiene 2 623tans61,369entadiene 2 622
A) 13 kG #ol61
%) 1+ kG #ol61
C) 20 kG #ol61
&) 23 kG #ol61
') 112 kG #ol61
Ans: %
Topic: eat of ydo-enation Section: 13.0
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0/. 'sti#ate the stabiliBation ene-y fo 1,36pentadiene "sin- the heats of hydo-enation inTable 1.
Table 1. eats of ydo-enation fo Selected Co#po"nds
Co#po"nd 8oles 2 (kG #ol61)
16%"tene 1 612/169entene
tans626pentene
1
1
612
611+1,36%"tadiene 2 623
tans61,369entadiene 2 622
A) 13 kG #ol61
%) 1+ kG #ol61
C) 20 kG #ol61
&) 23 kG #ol61
') 112 kG #ol61
Ans: %
Topic: eat of ydo-enation Section: 13.0
00. 'sti#ate the stabiliBation ene-y fo 1,36cyclohhe=adiene "sin- the heats of
hydo-enation in Table 1.
Table 1. eats of ydo-enation fo Selected Co#po"nds
Co#po"nd 8oles 2 (kG #ol61)
Cyclohe=ene 1 612
1,6Cyclohe=adiene 2 621,36Cyclohe=adiene 2 6232
1,+6e=adiene 2 62+3A) 13 kG #ol61
%) 21 kG #ol61
C) 0 kG #ol61
&) 12 kG #ol61
') 112 kG #ol61
Ans: C
-
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Topic:
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. Which of the follo!in- dienes #i-ht eact !ith bo#ine in CClto yield 2,+6dibo#o636he=ene$
A) C2CC2C2CC2%) C2CCCC2C3C) C3CCCC2C3&) C3CCCCC3') C3CCC2CC2
Ans: &
Topic: Con7"-ate Addition Reactions Section: 13.1
+. ndicate !hich pod"cts !o"ld be obtained fo# the chloination of 1,+6he=adiene at
hi-h te#peat"e (+C), "sin- a 1:1 #ole atio of the eactants.
C l C H 2 C H C H 2C H 2C H C H 2
*
C l
C H C H C H C H 2C lC l C H 2C H
C H C H 2C H C H 2C l C H 2C H
C H C H 2 C H C H C H 2
C H 2
C l
C l C H 2 C H C H 2C H 2 C H C H 2C l
C l C l
) ) )
) ) )
) *
A) and %) and
C) and *
&) * and *
') * and Ans: C
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Topic: 1,2 Reactions of Con7"-ated &ienes Section: 13.1
. Which ea-ent !o"ld conet 1,36pentadiene into 36penten626ol$
A) H8n464
%) 4s4
C) 242, then 34&) Cl224
') 34
Ans: '
Topic: 1,2 Reactions of Con7"-ated &ienes Section: 13.1
/. Which ea-ent !o"ld conet 1,36octadiene into 36octen626ol$
A) H8n464
%) 4s4C) 242, then 34
&) Cl224') 34
Ans: '
Topic: Con7"-ate Addition Reactions Section: 13.1
0. Which is the only co#po"nd !hich can be co#pletely "led o"t as a pod"ct of the
eaction of 1,36b"tadiene !ith Cl$
A) (S)636chloo616b"tene%) (R)636chloo616b"tene
C) (')616chloo626b"tene
&) (E)616chloo626b"tene
') (E)626chloo626b"teneAns: '
Topic: 8"ltistep Synthesis Section: 13.1 and peio"s chaptes
. o! co"ld the follo!in- synthesis be caied o"t$
C H 2C H 3
A) (1) %2CClI (2) C3C28-Cl, etheI (3) C345aC34
%) (1) %, 0CI (2) (C3C2)2C";i, ethe
C) (1) %, 0CI (2) 8-, etheI (3) C3C24, then 34
&) 8oe than one of the aboe') All of the aboe
Ans: %
Topic: 8"ltistep Reaction Se?"ence Section: 13.1 and peio"s chaptes
-
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1. o! co"ld the follo!in- synthesis be caied o"t$
A) (1) %2CClI (2) C38-Cl, etheI (3) C345aC34
%) (1) % (1 e?)I (2) (C3)2C";i, etheC) (1) % (1e?)I (2) ;i, etheI (3) C"I () C3%&) 8oe than one of the aboe
') All of the aboe
Ans: C
Topic: Reaction 8echanis#s and Contol Section: 13.1A
11. A the#odyna#ically6contolled eaction !ill yield pedo#inantly:
A) the #oe#ost stable pod"ct.
%) the pod"ct !hose fo#ation e?"ies the s#allest fee ene-y of actiation.
C) the pod"ct that can be fo#ed in the fe!est steps.&) the pod"ct that is fo#ed at the fastest ate.
') the pod"ct !hich possesses the -eatest potential ene-y.
Ans: A
Topic: Reaction 8echanis#s and Contol Section: 13.1A
12. An e?"ilibi"#6contolled eaction !ill yield pedo#inantly:A) the #oe#ost stable pod"ct.
%) the pod"ct !hose fo#ation e?"ies the s#allest fee ene-y of actiation.C) the pod"ct that can be fo#ed in the fe!est steps.
&) the pod"ct that is fo#ed at the fastest ate.
') the pod"ct !hich possesses the -eatest potential ene-y.Ans: A
Topic: Reaction 8echanis#s and Contol Section: 13.1A
13. A eaction "nde kinetic (o ate) contol !ill yield pedo#inantly:
A) the #ost stable pod"ct.%) the pod"ct that can be fo#ed in the fe!est steps.
C) the pod"ct !hose fo#ation e?"ies the s#allest fee ene-y of actiation.
&) the pod"ct !ith the -eatest potential ene-y.
') the pod"ct !ith the least potential ene-y.Ans: C
Topic: Reaction 8echanis#s and Contol Section: 13.1A
-
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1. The acco#panyin- dia-a#, !hich descibes the fate of the inte#ediate in a eesibleeaction, i#plies that:
A
%
'
eaction coodinateA) the less stable pod"ct fo#s #oe apidly.
%) the #oe stable pod"ct fo#s #oe apidly.
C) pod"ct % !ill pedo#inate at e?"ilibi"#.&) the inte#ediate has a shot lifeti#e.
') 5o concl"sions can be da!n as to eithe eaction ate o pod"ct stability.
Ans: %
Topic: Reaction 8echanis#s and Contol Section: 13.1A
1+. The acco#panyin- dia-a#, !hich descibes the fate of the inte#ediate in a eesible
eaction, i#plies that:
A) the less stable pod"ct fo#s #oe apidly.
%) the #oe stable pod"ct fo#s #oe apidly.
C) pod"ct % !ill pedo#inate at e?"ilibi"#.&) the inte#ediate has a shot lifeti#e.
') 5o concl"sions can be da!n as to eithe eaction ate o pod"ct stability.
Ans: A
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Topic: Reaction 8echanis#s and Contol Section: 13.1A
1. The acco#panyin- dia-a# i#plies that:
A
%'
eaction coodinateA) the fo#ation of % fo# A !o"ld be faoed at hi-h te#peat"e.%) the #oe stable pod"ct fo#s #oe apidly fo# the inte#ediate species.
C) the fo#ation of % fo# the inte#ediate is the ate6li#itin- step in the tansfo#ation
of A into %
&) the fo#ation of % fo# A is not a conceted eaction.') All of the aboe state#ents ae t"e.
Ans: '
Topic: &iels6Alde Reaction Section: 13.11
1/. Which is an "nt"e state#ent concenin- the &iels6Alde eaction$
A) The eaction is a syn addition.
%) The diene #"st be in the s6cis confo#ation to eact.C) 8ost &iels6Alde eactions ae eesible.
&) Jeneally, the add"ct fo#ed #ost apidly is the e=o pod"ct.
') 'lecton donatin- -o"ps on the diene and electon !ithda!in- -o"ps on thedieneophile fao add"ct fo#ation.
Ans: &
Topic: &iels6Alde Reaction Section: 13.11
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10. Which of these dienes can "nde-o the &iels6Alde eaction$A)
%)
C)
&)
') All of the aboe can "nde-o the &iels6Alde eaction.
Ans: A
Topic: &iels6Alde Reaction Section: 13.11
1. Which of these dienes can "nde-o the &iels6Alde eaction$
A)
%)
C)
&)
')
Ans: %
Topic: &iels6Alde Reaction Section: 13.11
-
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11. Which of the follo!in- can "nde-o the &iels Alde eaction$
*
*
A) and %) and
C) and *
&) , and *
') *Ans: C
Topic: &iels6Alde Reaction Section: 13.11
111. Ko# the standpoint of eactiity, !hich is the pooest choice of dienophile to eact !ith2,36di#ethyl61,36b"tadiene in a &iels6Alde eaction$
O
O O
H3CO
OCH3O
O
*
OCH3
H3CO
O
O
*A)
%)
C) &) *
') *
Ans: %
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Topic: &iels6Alde Reaction Section: 13.11
112. What is the pod"ct of the follo!in- eaction$
C H C H 2
C H 3C C C C C H 3
OO
$
C O C H 3
C O C H 3
C O C H 3
C O C H 3
C O C H 3
C O C H 3
C O C H 3
C O C H 3 C O C H 3
C O C H 3
) ) ) ) ) )
) * *
A) %)
C)
&) *') *
Ans: A
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Topic: &iels6Alde Reaction Section: 13.11
113. Which !o"ld be the best synthesis of the follo!in- co#po"nd$
C O 2C H 3C O 2C H 3
C O 2C H 3
C O 2C H 3
C O 2C H 3
C O 2C H 3
C O 2C H 3
C H 3O 2C
C O 2C H 3
C O 2C H 3
2 C 4 2 C 3
) ) ) ) ) )
) * *
A)
%)
C) &) *
') *Ans: %
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Topic: &iels6Alde Reaction Section: 13.11
11. Which eaction !o"ld pod"ce the follo!in- co#po"nd$
H
H
C O 2C H 3
C O 2C H 3
C O 2C H 3
C O 2C H 3
C O 2C H 3
C H 3O 2C
) ) )
) ) ) ) *
H
H
H
H
C O 2C H 3
C O 2C H 3
H
H
C O 2C H 3
C O 2C H 3
H
H
A)
%) C)
&) *
') 5one of the aboeAns: &
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Topic: &iels6Alde Reaction Section: 13.11
11+. Which of the follo!in- pais of co#po"nds co"ld be "sed as the basis fo a &iels6Alde
synthesis of the co#po"nd sho!n belo!$
C O 2C H 3
C H 3C H C H C H 32
C O 2C H 3
C H 3C H C H 2
C O 2C H 3
C H 2 C H C O 2C H 3
C H 2 C H C O 2C H 3
)
) )
) ) )
) *
A)
%)
C) &) *
') 8oe than one of the aboeAns: &
-
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Topic: &iels6Alde Reaction Section: 13.11
11. Which of the follo!in- pais of co#po"nds co"ld be "sed as the basis fo a &iels6Alde
synthesis of the co#po"nd sho!n belo!$
N
O
COOCH3
COOCH3
N
O
OCH3
O
H3CO
O
N
O
H3COOCCOOCH3
NH2
O
N
O
OCH3
O
H3CO
O
HN
N
O
**
A)
%)
C) &) *
') *
Ans: A
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Topic: &iels6Alde Reaction Section: 13.11
11/. Which of the follo!in- pais of co#po"nds co"ld be "sed as the basis fo a &iels6Aldesynthesis of the co#po"nd sho!n belo!$
O
O
O
O
O
O
O
O
O
O
O O
O
O
**
A)
%) C)
&) *
') *
Ans: %
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Topic: &iels6Alde Reaction Section: 13.11
110. Which of the follo!in- pais of co#po"nds co"ld be "sed as the basis fo a &iels6Alde
synthesis of the co#po"nd sho!n belo!$
O
O
O
O
O
O
O
O
O O
O
O
**
2 2
2
2
2
O
O
A)
%)
C) &) *
') *
Ans: %
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Topic: &iels6Alde Reaction Section: 13.11
11.
does not "nde-o the &iels6Alde eaction beca"se:
A) in- syste#s cannot f"nction as the diene co#ponent.
%) it cannot adopt thes-cisconfo#ation.C) it lacks electon6!ithda!in- -o"ps.
&) it lacks ston- electon6eleasin- -o"ps.
') the t!o do"ble bonds ae fathe apat than in a non6cyclic con7"-ated syste#.Ans: %
Topic: &iels6Alde Reaction Section: 13.11
12.
does not "nde-o the &iels6Alde eaction beca"se:
A) in- syste#s cannot f"nction as the diene co#ponent.
%) it cannot adopt thes-cisconfo#ation.C) it lacks electon6!ithda!in- -o"ps.
&) it lacks ston- electon6eleasin- -o"ps.
') the t!o do"ble bonds ae fathe apat than in a non6cyclic con7"-ated syste#.Ans: A
Topic: &iels6Alde Reaction Section: 13.11
121.
does not "nde-o the &iels6Alde eaction beca"se:A) in- syste#s cannot f"nction as the diene co#ponent.
%) it cannot adopt thes-cisconfo#ation.C) it lacks electon6!ithda!in- -o"ps.
&) it lacks ston- electon6eleasin- -o"ps.
') the t!o do"ble bonds ae fathe apat than in a non6cyclic con7"-ated syste#.Ans: %
Topic: &iels6Alde Reaction Section: 13.11
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122.
does not "nde-o the &iels6Alde eaction beca"se:
A) in- syste#s cannot f"nction as the diene co#ponent.
%) it cannot adopt thes-cisconfo#ation.
C) it lacks electon6!ithda!in- -o"ps.&) it lacks ston- electon6eleasin- -o"ps.
') the t!o do"ble bonds ae fathe apat than in a non6cyclic con7"-ated syste#.
Ans: %
Topic: &iels6Alde Reaction Section: 13.11
123.
does not "nde-o the &iels6Alde eaction beca"se:
A) in- syste#s cannot f"nction as the diene co#ponent.
%) it cannot adopt the s6cis confo#ation.C) it lacks electon6!ithda!in- -o"ps.
&) it lacks ston- electon6eleasin- -o"ps.
') the t!o do"ble bonds ae f"the apat than in a non6cyclic con7"-ated syste#.Ans: %
Topic: &iels6Alde Reaction Section: 13.11
12. Which of these dienes is the #ost eactie in the &iels6Alde eaction$
A)
%)
C)
&)
')
Ans: C
Topic: &iels6Alde Reaction Section: 13.11
12+. Which of the follo!in- dieneophiles is #ost eactie in a &iels6Alde eaction:
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O
O
O *
*
A) %)
C)
&) *') *
Ans: C
Topic: &iels6Alde Reaction Section: 13.11
12. Which of the follo!in- dieneophiles is #ost eactie in a &iels6Alde eaction:
*
*
NC CN
CNNC OCH3
OCH3
A) %)
C)
&) *') *
Ans: &
Topic: &iels6Alde Reaction Section: 13.11
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12/. Which diene and dienophile !o"ld yo" choose to synthesiBe the follo!in- co#po"nd$
H
C O C H 3
O
a n d C H 2 C H 2 a n d
a n d a n d
H C C C O C H 3
O
C H 2 C H C O C H 3
O
C H 2 C H C O C H 3
O
) ) )
) ) ) ) *
A)
%) C)
&) *
') 5one of theseAns: C
Topic: &iels6Alde Reaction Section: 13.11
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120. Which diene and dienophile !o"ld yo" choose to synthesiBe the follo!in- co#po"nd$
O
O
a n d C H
2 C H
2 a n d
a n d a n d
H C C C O C H 3
O
C H 2 C H C O C H 3
O
C H 2 C H C O C H 3
O
) ) )
) ) ) ) *
A)
%)
C) &) *
') 5one of these
Ans: %
Topic: &iels6Alde Reaction Section: 13.11
12. Which diene !o"ld be least eactie to!ad &iels6Alde addition of #aleic anhydide$
C H C H 2C HC H 2 C C H 2C HC H 2
C H 3
C C H 2CC H 2
C H 3C H 3
) ) ) ) ) )
) * *
A)
%)
C) &) *
') *Ans: '
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Topic: &iels6Alde Reaction Section: 13.11
13. What !o"ld be the pod"ct of the follo!in- eaction$
C H C C H 3C H 2
) ) ) ) ) ) ) *
O
h e a t
C
C H
C H 3
C H 2
C C
O
C H 3
O
C H 3
C
O
C H 3
A) %)
C)
&) *') All of these
Ans: C
Topic: &iels6Alde Reaction Section: 13.11
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131. Which diene and dienophile !o"ld yo" choose to synthesiBe the follo!in- co#po"nd$
O
O
H
H
O
O
O
O
O
**
A) %)
C)
&) *') 5one of these
Ans: A
Topic: &iels6Alde Reaction Section: 13.11
-
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132. Which of the follo!in- !o"ld affod a synthesis of the follo!in- co#po"nd$
C H O
C H 3C H C H C H 32
C H O
C H 3C H C H 2
C H O
C H 2 C H C H O
C H 2 C H C H O
)
) )
) ) )
) *
A) %)
C)
&) *
') 5one of these
Ans: &
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Topic: &iels6Alde Reaction Section: 13.11
133. What is the pod"ct of the follo!in- &iels6Alde cycloaddition eaction:
O
O
O
$
O
O
O
O
O
O
O
O
O
O
O
O
*
A) %)
C)
&) *') 5one of these
Ans: &
-
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Topic: &iels6Alde Reaction Section: 13.11
13. Which of the follo!in- !o"ld affod a synthesis of the follo!in- co#po"nd$
CHO
CHO
H
O
CHO
H
O
H
O
H
O
*
A)
%) C)
&) *
') 5one of theseAns: C
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Topic: &iels6Alde Reaction Section: 13.11
13+. Which of the follo!in- !o"ld affod a synthesis of the follo!in- co#po"nd$
CHO
H
O
OHC
H
O
H
O
H
O
*
CHO
A)
%)
C) &) *
') 5one of these
Ans: &
-
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Topic: &iels6Alde Reaction Section: 13.11
13. Which of the follo!in- !o"ld affod a synthesis of the follo!in- co#po"nd$
CHO
CHO
H
O
CHO
H
O
H
O
H
O
*
A)
%) C)
&) *
') 5one of theseAns: C
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Topic: &iels6Alde Reaction Section: 13.11
13/. Which diene !o"ld yo" e=pect to eact #ost apidly !ith #aleic anhydide$
C H 3
C H 3
C H 3
C H 3
C H 3C
C H 3C
O
O
) ) ) ) ) ) ) * *
A)
%)
C) &) *
') *
Ans: &
Topic: &iels6Alde Reaction Section: 13.11
130. Which of these con7"-ated dienes can "nde-o a &iels6Alde eaction$
C H 2 C H 2
C ( C H 3)3C H 2
( C H 3)3C
) ) ) ) ) ) ) * *
A)
%)
C) &) *
') *
Ans: C
Topic: &iels6Alde Reaction Section: 13.11
-
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13. Which of these con7"-ated dienes can "nde-o a &iels6Alde eaction$
O O
*
O
A)
%)
C) &) *
') All of the aboe
Ans: '
Topic: &iels6Alde Reaction Section: 13.11
1. Which of these dienes can "nde-o a &iels6Alde eaction$
* *
A) and *
%) , and *C)
&) *
') and *Ans: &
Topic: &iels6Alde Reaction Section: 13.11
-
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11. Which diene and dienophile !o"ld yo" choose to synthesiBe the follo!in- co#po"nd$
O
H
C O C H 3
O
C O C H 3
O
O
O O
a n d 4 2a n d
C H 2 C H C O C H 3
O
C H 2 C H C O C H 3
Oa n d a n d
H C C C O C H 3
O
) ) )
) ) ) ) *
A) %)
C)
&) *') 5one of these
Ans: C
Topic: &iels6Alde Reaction Section: 13.11
12. Which diene and dienophile !o"ld yo" choose to synthesiBe the follo!in- co#po"nd$
-
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S
CN
CN
S0 CN
S
S
S
*
CN
NCNC
CN
CNNC
A)
%)
C) &) *
') 5one of these
Ans: %
-
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Topic: &iels6Alde ReactionSection: 13.11
13. Which diene and dienophile !o"ld yo" choose to synthesiBe the follo!in- co#po"nd$
CHO
CHO
*
CHO
H
CHO
H
CHO
CHO
OHC
CHO
CHO
CHO
* *A) and *
%) and *
C) and *&) * and *
') and
Ans: '
-
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Topic: &iels6Alde Reaction Section: 13.11
1. Which diene and dienophile !o"ld yo" choose to synthesiBe the follo!in- co#po"nd$
CHO
CHO
*
CHO
CHO
OHC
CHO
CHO
CHO
* *
CHO
CHO
H
H
A) and *
%) and *C) and *
&) * and *
') and
Ans: A
Topic: &iels6Alde Reaction Section: 13.11
1+. Which co#po"nds co"ld be "sed in a &iels6Alde synthesis of
C H 2 C H C O 2C H 3 H C C C O 2C H 3
C H 3
C H 3
C O 2C H 3
$
C H 3
C H 3 C H 3
C H 3
) ) ) ) ) ) ) *
A) and
%) and *C) and
&) and *
Ans: C
-
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Topic: &iels6Alde Reaction Section: 13.11
1. Which is the #a7o pod"ct of the follo!in- eaction$
C
C
H C
CH
O H
O
O
O H
C O 2H
H
H
C O 2H
C O 2H
C O 2H
H
H
H
C O 2H
C O 2H
H
H
H
C O 2H
C O 2H
) ) ) ) ) ) ) *
$
A) %)
C)
&) *
') 5one of theseAns: &
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Topic: &iels6Alde Reaction Section: 13.11
1/. Which is the #a7o pod"ct of the follo!in- eaction$
HO2C
CO2H
$
C O 2H
H
H
C O 2H
C O 2H
C O 2H
H
H
H
C O 2H
C O 2H
H
H
H
C O 2H
C O 2H
) ) ) ) ) ) ) *
A)
%)
C) &) *
') 5one of these
Ans: A
Topic: &iels6Alde Reaction Section: 13.11
10. Which is the #a7o pod"ct of the follo!in- eaction$
CHO
H
H
CHO
*
H
H
CHO
CHO
CHO
CHO
H
H
H
CHO
CHO
H
*
H
H
CHO
CHO
CHO
CHO
$
A) %)
C)
&) *') *
Ans: A
-
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Topic: &iels6Alde Reaction Section: 13.11
1. Which is the #a7o pod"ct of the follo!in- eaction$
CHO
CHO
*
H
H
CHO
CHO
CHO
CHO
H
H
H
CHO
CHO
H
*
CHO
CHO
CHOOHC $
A)
%)
C) &) *
') *
Ans: &
Topic: &iels6Alde Reaction Section: 13.11
1+. Which is the #a7o pod"ct of the follo!in- eaction$
CHO
*
H
H
CHO
CHO
CHO
CHO
H
H CHO
*
CHO
CHO $
A)
%)
C) &) *
') *
Ans: C
-
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Topic: &iels6Alde Reaction Section: 13.11
1+1. Which diene and dienophile !o"ld yo" choose to synthesiBe the follo!in- co#po"nd$
C O C H 3
O
O
O
a n d 4 2a n d
C H 2 C H C O C H 3
O
C H 2 C H C O C H 3
Oa n d a n d
H C C C O C H 3
O
) ) )
) ) ) ) *
O
C O C H 3
O
A)
%)
C) &) *
') 5one of these
Ans: %
Topic: &iels6Alde Reaction Section: 13.11
1+2. Which of these dienes is the #ost eactie in the &iels6Alde eaction$
A) 1,36%"tadiene
%) 1,69entadiene
C) 2,3,6&i#ethyl61,36b"tadiene&) 1,26%"tadiene
') 1,6Cyclohe=adiene
Ans: C
Topic: &iels6Alde Reaction Section: 13.11
1+3. Which of these dienes can "nde-o the &iels6Alde eaction$A) 1,369entadiene
%) 1,69entadiene
C) 1,26%"tadiene&) 1,6Cyclohe=adiene
') All of the aboe can "nde-o the &iels6Alde eaction
Ans: A
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Topic: &iels6Alde Reaction Section: 13.11
1+. Which of these dienes can "nde-o the &iels6Alde eaction$
A) 1,26eptadiene
%) 1,36eptadieneC) 1,6eptadiene
&) 1,+6eptadiene
') 1,6eptadieneAns: %
Topic: &iels6Alde Reaction Section: 13.11
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1++. o! !o"ld yo" synthesiBe:
)
) )
) ) )
) *
O
H
C O C H 3
O
1 , 3 6 C y c l o h e = a d i e n e C H C O C H 3,C H 2
O
t h e n R C O O H
O
1 , 3 6 C y c l o h e = a d i e n e C H C O C H 3,C H 2
O
t h e nR C O O H ,
O
C O C H 3
O
C H 2
O
C H 2
1 , ( 6 C y c l o h e = a d i e n e C H C O C H 3,C H 2
O
t h e n
C H 2
O
C H 2
C O C H 3
O
O
C H 2C H 2*
A) %)
C)
&) *') *
Ans: A
SHORT ANSWER QUESTIONS
Topic: Jeneal Section: 13.1
1+. Syste#s that hae apobital on an ato# ad7acent to a do"ble bond ae called
LLLLLLLLLLLLLL syste#s.
Ans: con7"-ated "nsat"ated
Topic: Jeneal Section: 13.2
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1+/. The hydo-en ato# on a sat"ated (sp3) cabon ad7acent to a do"ble bond is called anLLLLLLLLLLLLLL hydo-en.
Ans: allylic
Topic: Jeneal Section: 13.2
1+0. The hydo-en ato# on a cabon that is pat of a do"ble bond is called a LLLLLLLLLLL
hydo-en.Ans: inyl o inylic
Topic: Jeneal Section: 13.2
1+. Allylic adicals ae LLLLLLLLLLL stable than tetiay adicals.
Ans: #oe
Topic: Jeneal Section: 13.
1. *inyl cations ae LLLLLLLLLLLLL stable than tetiay cations.
Ans: less
Topic: Jeneal Section: 13.
11. Thee ae thee types of polyenes (#olec"les containin- t!o o #oe do"ble bonds).
They ae: LLLLLLLLLLLLLLLLL.Ans: con7"-ated, c"#"lated, isolated
Topic: Jeneal Section: 13.
12. 9olyenes in !hich sin-le and do"ble bonds altenate alon- the cabon chain ae called
LLLLLLLLLLL.Ans: con7"-ated
Topic: 5o#enclat"e Section: .+, ., +./, and 13.
13. &a! the st"ct"al fo#"la fo (R)-+6bo#o62,+6di#ethyl61,36cyclopentadiene, clealy
indicatin- steeoche#ical details.
Ans: CH3Br
Topic: 5o#enclat"e Section: .+, ., /.2 and 13.
1. &a! the st"ct"al fo#"la fo (2',E,')>3,,/,0>teta#ethyl62,,>nonatiene,
clealy indicatin- steeoche#ical details.
Ans:
-
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Topic: 5o#enclat"e Section: .+, ., /.2 and 13.
1+. &a! the st"ct"al fo#"la fo (2E,E,E)63,,06ti#ethyl62,,6nonatiene, clealyindicatin- steeoche#ical details.
Ans:
Topic: Jeneal Section: 13.
1.
-
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&Cl
Ans:
Cl
D
Cl
D
Topic: Jeneal Section: 13.11
1/3. The &iels6Alde eaction is a cycloaddition bet!een a con7"-ated LLLLLLLL and aLLLLLLLLLLL.
Ans: dieneI dienophile
Topic: Jeneal Section: 13.11
1/. Steeoche#ically speakin-, the &iels6Alde eaction is LLLLLLLLLLL and occ"s !ith
LLLLLLLLLLL of the dienophile steeoche#isty.Ans: steeospecificI etention
Topic: &iels6Alde Reactions Section: 13.11
1/+. &"in- &iels6Alde eactions, !hen t!o steeoiso#e pod"cts, exo and endo, ae
possible, the LLLLLLLLLLL pod"ct is typically obtained as the #a7o pod"ct.Ans: endo
Topic: &iels6Alde Reaction Section: 13.11
1/. What ea-ents !o"ld be needed to synthesiBe the follo!in- s"bstance ia the &iels6
Alde eaction$ Jie steeoche#ical details, as eleant.
O
O
O
Ans:
O
O
O
Topic: &iels6Alde Reaction Section: 13.11
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1//. Which diene and dienophile !o"ld yo" "se to pepae the follo!in- #olec"le "sin- a &iels6
Alde cycloaddition eaction:
o
H
H
O
O
Ans:
O
O
O
Topic: &iels6Alde Reaction Section: 13.11
1/0. Which diene and dienophile !o"ld yo" "se to pepae the follo!in- #olec"le "sin- a &iels6
Alde cycloaddition eaction:
CHO
CHO
Ans:
OHC CHO
Topic: &iels6Alde Reaction Section: 13.11
1/. The fist step in the total synthesis of synthetic cholesteol inoles pod"ction of the
inte#ediate st"ct"e sho!n. Which co#bination of diene and dieneophile !ill es"lt in
its pepaation$
HH3CO
O
O
Ans:
-
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O
O
H3CO
Topic: &iels6Alde Reaction Section: 13.11
10. The st"ct"e belo! is an inte#ediate alon- the !ay to the pod"ction of synthetic
#ophine. t is pod"ced tho"-h a &iels6Alde cycloaddition eaction. Whichco#bination of diene and dieneophile !ill es"lt in its pepaation$
H3CO
OCH3
O
O
CN
Ans:
H3CO
OCH3
O
O
CN
Topic: &iels6Alde Reaction Section: 13.11
101. What co#bination of diene and dieneophile can be "sed to pepae the follo!in-
co#po"nd tho"-h a &iels6Alde cycloaddition eaction:
N
O
COOCH3
COOCH3
Ans:
N
O
OCH3
O
H3CO
O
-
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Topic &iels6Alde Reaction Section: 13.11
102. 9edict the pod"ct of the follo!in- &iels6Alde cycloaddition eaction:
CN
S
NC
Ans:
S
CN
CN
Topic &iels6Alde Reaction Section: 13.11
103. Steoids ae nat"ally occ"in- polycyclic co#po"nds classified as lipids. The &iels6
Alde eaction has been !idely "sed in thei pepaation. Sho!n belo! is a pec"so
#olec"le "sed in a total steoid synthesis. What co#bination of diene and dieneophile can
be "sed to pepae this co#po"nd tho"-h the "se of a &iels6Alde cycloaddition eaction.
H3CO
O
O
Ans:
H3CO
O
O
-
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Topic: &iels6Alde 8echanis# Section: 13.11
10. &a! ao!s to indicate the electon flo! fo the follo!in- inta#olec"la &iels6Aldecycloaddition eaction:
O O
N
O
Ph
O
O
N
O
Ph
Ans:
O O
N
O
Ph
O
O
N
O
Ph
-
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Topic: &iels6Alde 8echanis# Section: 13.11
10+. &a! ao!s to indicate electon #oe#ent that e=plains the fo#ation of the pod"ctssho!n fo the follo!in- eto6&iels6Alde eaction:
o
o
CN
CN
CN
CN
C42
Ans:
o
o
CN
CN
CN
CN
C42
Topic: &iels6Alde Reaction Section: 13.11
10. The co#po"nd sho!n belo! "nde-oes a eto6&iels6Alde cycloaddition eaction to yieldcabon dio=ide and anothe co#po"nd. 9edict the st"ct"e of the othe co#po"nd
fo#ed.
O
O
CN
CN
C42 $
Ans:
CN
CN
-
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Topic: &iels6Alde Reaction Section: 13.11
10/. The alkaloid colchicine is "sed in the teat#ent of -o"t. The fist synthetic colchineinoled the pepaation of the key inte#ediate sho!n. Which co#bination of diene and
dieneophile !ill es"lt in its pepaation$H3CO
H3CO
OCH3
OO
O
O
O
Cl
Ans:
H3
CO
H3CO
OCH3
O
O
O
O
O
Cl
Topic: &iels6Alde Reaction Section: 13.11
100. Which diene and dienophile !o"ld yo" "se to pepae the follo!in- #olec"le "sin- a &iels6
Alde cycloaddition eaction:
CN
CN
Ans:
NC CN
-
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Topic: 8"ltistep Reactions Section: 13.11 and peio"s chaptes
10. Co#plete the follo!in- se?"ence of eactions, -iin- st"ct"al details of all key
inte#ediates.O
O
heat
A %125i
Ans:
O
O
heat
O
O
O
O
12, 5i
O
O
O
O
O
O
O
O
Topic: 8"ltistep Reactions Section: 13.11 and peio"s chaptes
-
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1. Co#plete the follo!in- se?"ence of eactions, -iin- st"ct"al details of all keyinte#ediates.
i) cis-C3C:CC4
ii) C3C28-%
iii) 34
$
Ans:
CHO CH3
O
H
HCH3
HO
H
Hi) C3C28-%ii) 34
Topic: 8"ltistep Reactions Section: 13.2, 13.3, 13.11 and peio"s chaptes
11. Co#plete the follo!in- se?"ence of eactions, -iin- st"ct"al details of all keyinte#ediates.
i) 5%S
ii) (C13)3C4H, (C13)3C41, heat
iii) tans C13C1:C1C14
$
Ans:
O
5%S
Br
(C3)3C4H,
(C3)3C4,
heat