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Organic chemistry I N-attack notes (weekend quiz hellp)

by: Tiffany Thomas

Organic chemistry I N-attack notes (weekend quiz hellp) CHEM 07200 1

Marketplace > Rowan University > CHEM 07200 1 > Organic chemistry I N attack notes weekend quiz hellp
Tiffany Thomas
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these notes/sample quiz covers everything about N-attacks
Nazer, Behrooz
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This 4 page Class Notes was uploaded by Tiffany Thomas on Monday January 18, 2016. The Class Notes belongs to CHEM 07200 1 at Rowan University taught by Nazer, Behrooz in Fall 2015. Since its upload, it has received 234 views.


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Date Created: 01/18/16
Weekend Quiz 5-N-attack!! Q1.  Identify  the  nucleophilic  atom  in  the  following   Q6.  Which  of  the  following  is  hydride?  (Hydride  is  a   molecule.  (Hint:  looking  for  extra  electrons!!!)   hydrogen  with  an  extra  electron)   Me P 3   A.    H A.    P   B.    H   C.    H   B.    C   C.    H   D.  2  H   D.    Me   Ans:    C   Ans:    A       Q7.  Which  of  the  following  is  the  most  stable  cation?   Q2.  Identify  the  electrophilic  atom  in  the  following   (remember  more  carbon  bonded  to  carbocation   makes  it   molecule.  (Hint:  look  at  carbon  oxygen  bond!    Where  are   happier!)   the  electrons?  Electronegativity?)   A. B. O   A. B. C. D. A.    C   B.    H   Ans:    C   C.    O  of  carbonyl   D.    C  of  carbonyl     Q8.  For  the  following  reaction  step,  indicate  which  pattern   Ans:    D   it  belongs  to.    (What  does  THE  arrow  is  telling  us?)     Q3.  Identify  the  electrophilic  site  in  the  following  molecule.   O H O H (Hint  which  one  is  more  electronegative  B  or  O?)     B A.    Proton  Transfer   O O B.    Loss  of  Leaving  Group   C.    Nucleophilic  Attack     D.    Rearrangement   A.    C   Ans:    A   B.    O     C.    B   Q9.  For  the  following  reaction  step,  indicate  which  pattern   it  belongs  to.(  Oxygen  in  methanol  has  electrons  and   D.    No  electrophilic  site   Ans:    C   carbon  attached  to  oxygen  is  losing  its  electrons     because….and  if  carbon  is  losing  its  electrons  what  are  we   going  to  call  it?)   Q4.  Which  of  the  following  cannot  be  a  nucleophile?  (what   does  a  nucleophile  have?)   H H O MeOH H O OH C. D. Br OMe A. B.       A.    Proton  Transfer   OH C. D. Br B.    Loss  of  Leaving  Group   A. B.   C.    Nucleophilic  Attack   Ans;    A   D.    Rearrangement     Ans:    C   Q5.  Which  of  the  following  cannot  be  an  electrophile?     (What  does  an  electrophile  need?)   Q10.  For  the  following  reaction  step,  indicate  which     pattern  it  belongs  to.  (somebody  is  leaving!)   OH D. Br A. B. C. OH   2 A. B. OH C. D. Br     A.    Proton  Transfer     Ans:    D   B.    Loss  of  Leaving  Group   C.    Nucleophilic  Attack     D.    Rearrangement     Ans:    B   Weekend Quiz 5-N-attack!!   Q15.    What  is  wrong  with  the  following  mechanism?  (oh  no   Q11.  For  the  following  reaction  step,  indicate  which   no  where  is  the  arrow  going?)   pattern  it  belongs  to.  (little  H+  is  finding  a  new  home!)   H 2 Br Br OH OH 2 H   A.    There  is  no  leaving  group,  so  there  should  be  no  arrows.   B.    The  arrow  should  be  removing  a  proton  from  the  H O     2 A.    Proton  Transfer   group.   B.    Loss  of  Leaving  Group   C.  An  arrow  is  also  needed  to  indicate  the  loss  of  the   C.    Nucleophilic  Attack   leaving  group.   D.    Rearrangement   D.  The  arrow  indicating  the  formation  of    the  C -­‐Br  bond   Ans:    A   (nucleophilic  attack)  should  start  at  the  bromide  anion.     Ans:    D   Q12.  For  the  following  reaction  step,  indicate  which     pattern  it  belongs  to.  (Making  a  better  carbocation!!!)   Q16.    Which  of  the  following  is  the  correct  mechanism  for  a   nucleophilic  attack  pattern?  (sorry  running  out  of  idea!)   A. B. H H2O Br Br H2O Br Br   A.    Proton  Transfer   B.    Loss  of  Leaving  Group   C.    Nucleophilic  Attack   C. H 2 Br D. H 2 Br D.    Rearrangement   Br Br Ans:    D       Ans:    B   Q13.  For  the  following  reaction  step,  indicate  which     pattern  it  belongs  to.  (oh  bromine  is  doing  something?)   Q17.  Which  of  the  following  is  the  correct  mechanism  for  a   loss  of  leaving  group  pattern?   Br Br A. OH OH 2 H B. Br Br   A.    Proton  Transfer   B.    Loss  of  Leaving  Group   OH 2 D. C.    Nucleophilic  Attack   C. H D.    Rearrangement     Ans:    C       Ans:    C   Q14.  What  is  wrong  with  the  following  mechanism?     (Remember  how  many  arrows  do  we  need  to  have  to  show   Q18.  Identify  the  sequence  of  steps  in  the  following   a  brand  new  compound  is  forming!!  A  beautiful  2 -­‐ reaction.  (oh  adding,  going  away!)   bromobutane  I  am  not  going  to  drink  it  because  it  is  toxic)   H O H O O H O H 2 Br Br H   A.    Proton  transfer,  Proton  transfer   B.    Proton  transfer,  Loss  of  leaving  gro up     A.    There  is  no  leaving  group,  so  there  should  be  no  arrows.     Nucleophilic  attack,  Proton  transfer   D.    Proton  transfer,  Nucleophilic  attack   B.    The  arrow  should  be  removing  a  proton  from 2the  H O   group.   Ans:    A   C.  An  arrow  is  also  needed  to  indicate  the  loss  of  the   leaving  group.   D.    The  arrow  is  backwards.   Ans:  C         Weekend Quiz 5-N-attack!!   B.    Loss  of  Leaving  Group   Q19  Identify  the  sequence  of  steps  in  the  following   C.    Nucleophilic  Attack   reaction.  (you  should  know  it  by  now:  adding,  attacking,D.    Rearrangement   and  leaving  home)   Ans:    B     O H H H H H Q23  What  pattern  is  the  fourth  step  of  this  reaction?   O MeOH O OMe O OMe O H O O   N OH A.    Proton  transfer,  Proton  tran sfer,  Nucleophilic  Attack O   N OH 2 N O O B.    Proton  transfer,  Loss  of  leaving  group   C.    Nucleophilic  attack,  Proton  transfer,  Loss  of  leaving   group   D.    Proton  transfer,  Nucleophilic  attack,  Proton  transfer   O N O 2 2 Ans:    D   H     Q20.  Identify  the  sequence  of  steps  in  the  following  A.    Proton  Transfer   reaction.   B.    Loss  of  Leaving  Group   O C.    Nucleophilic  Attack   H O O D.    Rearrangement   N OH N OH N O O 2 O Ans:    A     Q24.  What  pattern  is  the  second  step  of  this  reaction?   O N O2N 2 H H Cl Cl Cl     A.    Proton  transfer,  Proton  transfer,  Nucleophilic  Attack A.    Proton  Transfer   B.    Proton  transfer,  Loss  of  leaving  group,  Nucleophilic   B.    Loss  of  Leaving  Group   attack,  Proton  transfer   C.    Nucleophilic  Attack   C.    Nucleophilic  attack,  Proton  transfer,  Loss  of  leaving   D.    Rearrangement   group   Ans:    C   D.  Proton  transfer,  Loss  of  leaving  group,  P roton  transfer,     Nucleophilic  attack   Q25.  What  pattern  is  the  second  step  of  this  reaction?   Ans:    B     O H O O   N OH N O N OH 2 O Q21.  Identify  the  sequence  of  steps  in  the  following   O reaction.   O 2 H Cl Cl O 2 Cl H     A.    Proton  Transfer   A.    Proton  transfer,  Proton  transfer   B.    Loss  of  Leaving  Group   B.    Proton  transfer,  Loss  of  leaving  group   C.    Nucleophilic  Attack   C.    Nucleophilic  attack,  Proton  transfer   D.    Rearrangement   D.    Proton  transfer,  Nuc leophilic  attack   Ans:    B   Ans:    D         Q22.  What  pattern  is  the  second  step  of  this  reaction    O H O   N OH O   O N OH 2 N O O O N O 2 2 H   A.    Proton  Transfer   Weekend Quiz 5-N-attack!!   A. B. C. D. Q26.  What  pattern  is  the  second  step  of  this  reaction?     HO OH H HO OH 2 HO   Ans:    B     Q31  Will  the  following  cation  undergo  rearrangement?   O H O HO     A. Yes   A.    Proton  Transfer   B. No   B.    Loss  of  Leaving  Group   C.    Nucleophilic  Attack     Ans:    Yes   D.    Rearrangement   Ans:    B     Q32.  Which  of  the  following  is  the  structure  of  the     following  cation  after  rearrangement?   Q27  Which  of  the  following  is  the  nucleophilic  site  in  the   following  reaction?   A. B. C. D. O O Ans:    D   Li Me       A.    C  of  the  carbonyl   Q33.  Which  of  the  following  is  the  structure  of  the   B.    O   following  cation  after  rearrangement?  (making  better   carbocations!!!  You  can  make  more  money  by  selling  a   C.    Li   D.    Me  of  Li-­‐Me   better  carbocation  on  Ebay)   Ans:    D   A. B. C. D.     Q28.  Which  of  the  following  is  the  electrophilic  site  in  the       following  reaction?   Ans:    A   O O   Li Me         A.    C  of    the  carbonyl   B.    O   C.    Li   D.    Me   Ans:    A       Q29.  Which  of  the  following  is  the  electrophilic  site  in  the   following  reaction?   O O HOMe Cl OMe   A.    C  of  carbonyl   B.    O  of  carbonyl   C.    Cl   D.    O  of  alcohol   Ans:    A       Q30.  Which  of  the  following  cations  is  likely  to  undergo   rearrangement?  


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