ch13 problems

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: %


2. Which fee adical !o"ld be least stable$

A)

%)

C)

&)

')

Ans: &


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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


. Which fee adical !o"ld be #ost stable$

**

A) %)

C)

&) *') *

Ans: C


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+. Which fee adical !o"ld be least stable$

**

A)

%)

C) &) *

') *

Ans: '


.

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: &



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/.


*

*

isae #ost s"sceptible to abstactionby fee adicals$

A) %)

C)

&) *') *

Ans: %


0.


*

*

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


1. The allyl adical has ho! #any electons in bondin- #olec"la obitals$

A) 1

%) 2

C) 3&)

') +

Ans: %


1+. The allyl adical has ho! #any electons in non6bondin- #olec"la obitals$

A) 1

%) 2

C) 3&)

') +

Ans: A



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1. The allyl adical has ho! #any #olec"la obitals$

A) 1

%) 2

C) 3&)

') +

Ans: C


1/. The 484 of the allylic adical has ho! #any electons in its -o"nd state$A) 1

%) 2

C) 3&)

')

Ans: A


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: %


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: %



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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



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33. Which cabocation !o"ld be least stable$

A)

%)

C)

&)

')

Ans: &


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


3+. Which cabocation !o"ld be #ost stable$

* *

A)

%) C)

&) *

') *Ans: C


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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: %


30. The allyl cation has ho! #any bondin- #olec"la obitals$

A) 1%) 2

C) 3

&) ') +

Ans: A


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


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: %



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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: &



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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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. Which pai does not epesent a pai of esonance st"ct"es$

and

and

and

and

*

A) %)

C)


Ans: '


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+. Which pai does not epesent a pai of esonance st"ct"es$

and

and

and

and

*

A) %)

C)


Ans: '

Topic: Alkene Classification Section: 13.


19/84

. Select the st"ct"e of the con7"-ated diene.

) ) ) ) ) ) ) * *

A) %)

C)

&) *') *

Ans: %


/. Select the st"ct"e of the con7"-ated diene.

* *

A)

%) C)

&) *

') *

Ans: C



20/84

0. Select the st"ct"e of the con7"-ated diene.

* *

A) %)

C)

&) *

') *Ans: C


. Select the st"ct"e of the isolated diene.

* *

A) %)

C)

&) *

') *Ans: &


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+. Select the st"ct"e(s) of the con7"-ated diene(s).

* *

A) and

%) and C) and *

&) , and *

') *

Ans: C


+1. Which of the follo!in- dienes is a c"#"lated diene$

A) C2CC2C2CC2%) C2CCCC2C3C) C3CCCC2C3&) C3CCCCC3') C3CCC2CC2

Ans: C


+2. Which of the follo!in- dienes is a c"#"lated diene$

A) C2CC2C2C2CC2%) C2CCCC2C2C3C) C3CCCC2C2C3&) C3CCCCC2C3') C3C2CCC2CC2

Ans: C



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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


+. 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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. 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


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: %


3. 1,36b"tadiene has ho! #any bondin- #olec"la obitals$

A) 1

%) 2

C) 3&)

')

Ans: %


25/84


. 1,369entadiene has ho! #any antibondin- #olec"la obitals$

A) 1

%) 2C) 3

&)

') Ans: %


+. 1,36b"tadiene has ho! #any electons in its -o"nd state bondin- #olec"la obitals$

A) 1

%) 2

C) 3&)

') Ans: &


. 1,36b"tadiene has ho! #any electons in its -o"nd state antibondin- #olec"la

obitals$

A) 1%) 2

C) 3

&) ')

Ans: '


/. The 484 of 1,36pentadiene has ho! #any electons in its -o"nd state$

A) 1%) 2

C) 3

&) ')

Ans: %



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0. The ;


27/84

/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


/. 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


/. 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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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: '



30/84

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: &


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



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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: '


0. Which alkene !o"ld yo" e=pect to hae the s#allest heat of hydo-enation$

A)

%)

C)

&)

')Ans: '


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


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: %



33/84

0/. 'sti#ate the stabiliBation ene-y fo 1,36pentadiene "sin- the heats of hydo-enation inTable 1.



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: %


00. 'sti#ate the stabiliBation ene-y fo 1,36cyclohhe=adiene "sin- the heats of

hydo-enation in Table 1.



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


37/84

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


38/84

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


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


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



39/84

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: %


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


40/84


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: &



41/84

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


1. Which of these dienes can "nde-o the &iels6Alde eaction$

A)

%)

C)

&)

')

Ans: %



42/84

11. Which of the follo!in- can "nde-o the &iels Alde eaction$

*

*

A) and %) and

C) and *

&) , and *

') *Ans: C


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: %


43/84


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


44/84


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: %


45/84


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: &


46/84


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: &


47/84


11. Which of the follo!in- pais of co#po"nds co"ld be "sed as the basis fo a &iels6Alde


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


48/84


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: %


49/84


110. Which of the follo!in- pais of co#po"nds co"ld be "sed as the basis fo a &iels6Alde


O

O

O

O

O

O

O

O

O O

O

O

**

2 2

2

2

2

O

O

A)

%)

C) &) *

') *

Ans: %


50/84


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: %


12.





') the t!o do"ble bonds ae fathe apat than in a non6cyclic con7"-ated syste#.Ans: A


121.

does not "nde-o the &iels6Alde eaction beca"se:A) in- syste#s cannot f"nction as the diene co#ponent.



') the t!o do"ble bonds ae fathe apat than in a non6cyclic con7"-ated syste#.Ans: %



51/84

122.



%) 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: %


123.



%) it cannot adopt the s6cis confo#ation.C) it lacks electon6!ithda!in- -o"ps.


') the t!o do"ble bonds ae f"the apat than in a non6cyclic con7"-ated syste#.Ans: %


12. Which of these dienes is the #ost eactie in the &iels6Alde eaction$

A)

%)

C)

&)

')

Ans: C


12+. Which of the follo!in- dieneophiles is #ost eactie in a &iels6Alde eaction:


52/84

O

O

O *

*

A) %)

C)

&) *') *

Ans: C


12. Which of the follo!in- dieneophiles is #ost eactie in a &iels6Alde eaction:

*

*

NC CN

CNNC OCH3

OCH3

A) %)

C)

&) *') *

Ans: &



53/84

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



54/84

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: %


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: '


55/84


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



56/84


O

O

H

H

O

O

O

O

O

**

A) %)

C)

&) *') 5one of these

Ans: A



57/84

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: &


58/84


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)


Ans: &


59/84



CHO

CHO

H

O

CHO

H

O

H

O

H

O

*

A)

%) C)

&) *



60/84


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: &


61/84



CHO

CHO

H

O

CHO

H

O

H

O

H

O

*

A)

%) C)

&) *



62/84


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: &


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



63/84

13. Which of these con7"-ated dienes can "nde-o a &iels6Alde eaction$

O O

*

O

A)

%)

C) &) *

') All of the aboe

Ans: '


1. Which of these dienes can "nde-o a &iels6Alde eaction$

* *

A) and *

%) , and *C)

&) *

') and *Ans: &



64/84


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)


Ans: C




65/84

S

CN

CN

S0 CN

S

S

S

*

CN

NCNC

CN

CNNC

A)

%)

C) &) *

') 5one of these

Ans: %


66/84

Topic: &iels6Alde ReactionSection: 13.11


CHO

CHO

*

CHO

H

CHO

H

CHO

CHO

OHC

CHO

CHO

CHO

* *A) and *

%) and *

C) and *&) * and *

') and

Ans: '


67/84



CHO

CHO

*

CHO

CHO

OHC

CHO

CHO

CHO

* *

CHO

CHO

H

H

A) and *

%) and *C) and *

&) * and *

') and

Ans: A


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


68/84


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: &


69/84


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



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


70/84



CHO

CHO

*

H

H

CHO

CHO

CHO

CHO

H

H

H

CHO

CHO

H

*

CHO

CHO

CHOOHC $

A)

%)

C) &) *

') *

Ans: &


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


71/84


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: %


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


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


72/84


1+. Which of these dienes can "nde-o the &iels6Alde eaction$

A) 1,26eptadiene

%) 1,36eptadieneC) 1,6eptadiene

&) 1,+6eptadiene

') 1,6eptadieneAns: %



73/84

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



74/84

1+/. The hydo-en ato# on a sat"ated (sp3) cabon ad7acent to a do"ble bond is called anLLLLLLLLLLLLLL hydo-en.

Ans: allylic


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


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


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


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


1. &a! the st"ct"al fo#"la fo (2',E,')>3,,/,0>teta#ethyl62,,>nonatiene,

clealy indicatin- steeoche#ical details.

Ans:


75/84


1+. &a! the st"ct"al fo#"la fo (2E,E,E)63,,06ti#ethyl62,,6nonatiene, clealyindicatin- steeoche#ical details.

Ans:


1.


76/84

&Cl

Ans:

Cl

D

Cl

D


1/3. The &iels6Alde eaction is a cycloaddition bet!een a con7"-ated LLLLLLLL and aLLLLLLLLLLL.

Ans: dieneI dienophile


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


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



77/84

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


1/0. Which diene and dienophile !o"ld yo" "se to pepae the follo!in- #olec"le "sin- a &iels6


CHO

CHO

Ans:

OHC CHO


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:


78/84

O

O

H3CO


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


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


79/84

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


80/84

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


81/84

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


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


82/84


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


100. Which diene and dienophile !o"ld yo" "se to pepae the follo!in- #olec"le "sin- a &iels6


CN

CN

Ans:

NC CN


83/84

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


84/84

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

ch13 problems

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