Exam 3 reminders

Question 1

Elimination or Substitution?

H₂SO₄

Answer 1

Elimination

(dehydration)

Question 2

Elimination or Substitution?

NaH

Answer 2

Eliminates H from hydroxyl group

Question 3

Elimination or substitution?

HCl w/ ZnCl₂

Answer 3

Substitution

Question 4

Elimination or Substitution?

HBr

Answer 4

Substitution

Question 5

Elimination or Substitution?

SOCl₂ w/ pyr

Answer 5

Substitution

Question 6

Elimination or Substitution?

PBr₃

Answer 6

Substitution

Question 7

Elimination or Substitution?

TsCl w/ pyr

Answer 7

Substitution

Question 8

Elimination or substitution?

NaH w/ CH₂CH₃Br

Answer 8

Elimination of H from OH

then, O^- attacks C on the alkyl halide

Question 9

Elimination or Substitution?

TsCl w/ pyr

NaSH

Answer 9

Substitution to OTs…..then substitution to SH

Question 10

Elimination or substitution?

POCl₃ w/ pyr

Answer 10

Elimination

Question 11

What can be used to break open an epoxide ring?

Answer 11

^-OH & H₂O

Question 12

What can be used to change alcohol to Br?

Answer 12

PBr₃ or HBr

Question 13

What can be used to remove Br and form alkene?

Answer 13

t-BuO or KOC(CH₃)₃

(essentially a strong base)

Question 14

What is used to convert alcohol into OTs?

Answer 14

TsCl

Question 15

What can be used to remove OTs and form an alkene?

Answer 15

t-BuO or KOC(CH₃)₃

Strong base!

Question 16

What does H₂O & H₂SO₄ do to an alkene?

Answer 16

Adds OH to most substituted.

Question 17

What does an alcohol do to an alkene?

Ex: Alkene + CH₃CH₂OH + H₂SO₄

Answer 17

Makes an ether on most substituted.

Question 18

What does Cl₂ do to an alkene?

Answer 18

Adds two Cl’s: 1 on most substituted, 1 on least.

Question 19

What does Br₂ and H₂O do to an alkene?

Answer 19

Adds OH to most substituted and Br to least.

Question 20

What does NBS and DMSO (aq) do to alkene?

Answer 20

Adds OH to most substituted and Br to least.

Question 21

What does BH₃ and H₂O₂ and OH do to alkene?

Answer 21

Adds primary OH

Question 22

Hydroboration-oxidation results in the addition of an OH group on the ____ substituted carbon.

Acid-catalyzed addition of H2O results in the addition of an OH group on the _____ substituted carbon.

Answer 22

less

more

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Question 28

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Question 60

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Question 61

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Question 62

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Question 63

Formula for degrees of separation

Answer 63

(2n +2) - (#H) / 2