Final Exam from 352

Question 1

What reagents would you use for alkylation on the more substitued carbon?

Answer 1

(CH₃)₃CO^- (t-Butoxide)

——————>

R-Br, R-Cl, R-I

or

NaH

——————>

R-Br, R-Cl, R-I

Question 2

What reagents would you use for alkylation on the less substitued carbon?

Answer 2

1) LDA

—————–>

2) R-Br, R-Cl, R-I

Question 3

What reagents would you use for exhaustive halogenation?

Answer 3

NaOH

—————->

Br₂

Question 4

What reagents would you use for single halogenation?

Answer 4

HOAc

——————–>

Br₂

Question 5

What reagent(s) would you use for this reaction?

Answer 5

NaNH₂ (2 equiv)

Question 6

What reagent(s) would you use for this reaction?

Answer 6

NaNH₂ (1 equiv)

Question 7

What reagent(s) would you use for this reaction?

Answer 7

1) NaNH₂ (3 equiv)

————————>

2) H₃O⁺

Question 8

What reagent(s) would you use for this reaction?

Answer 8

1) NaNH₂ (2 equiv)

————————>

2) H₃O⁺

Question 9

What reagent(s) would you use for this reaction?

Answer 9

H-X

(X= Br, Cl, I)

Question 10

What reagent(s) would you use for this reaction?

Answer 10

X₂

———>

H₂O

*anti addition

Question 11

What reagent(s) would you use for this reaction?

Answer 11

X₂

————>

ROH

Question 12

What reagent(s) would you use for this reaction?

Answer 12

1) Hg(OAc)₂

H₂O

——————–>

2) NaBH₄

Question 13

What reagent(s) would you use for this reaction?

Answer 13

1) Hg(OAc)₂

ROH

——————–>

2) NaBH₄

Question 14

What reagent(s) would you use for this reaction?

Answer 14

1) BH₃

————>

2) H₂O₂, ^-OH

anti-markovnikov - OH on less subst. carbon

Question 15

What reagent(s) would you use for this reaction?

Answer 15

CH₂I₂

Zn(Cu)

or

CH₂N₂

hv

Question 16

What reagent(s) would you use for this reaction?

Answer 16

H₂O

TfOH

or

Hg₂⁺, H₂O

H₂SO₄

Question 17

What reagent(s) would you use for this reaction?

Answer 17

H-X

(X= Br, Cl, I)

Question 18

What reagent(s) would you use for this reaction?

Answer 18

CH₃O^-

Question 19

What reagent(s) would you use for this reaction?

Answer 19

H-X

Question 20

What reagent(s) would you use for this reaction?

Answer 20

PBr₃

Question 21

What reagent(s) would you use for this reaction?

(alkyne → aldehyde)

Answer 21

1) Sia₂BH

———————>

2) H₂O₂, NaOH

Question 22

What reagent(s) would you use for this reaction?

Answer 22

CH₂N₂

hv

Question 23

What reagent(s) would you use for this reaction?

Answer 23

LiAlH₄

or

NaBH₄

Question 24

What reagent(s) would you use for this reaction?

(Aldhyde → 1° Alcohol)

Answer 24

LiAlH₄

or

NaBH₄

Question 25

What reagent(s) would you use for this reaction?

Answer 25

1) R-MgX

———————>

2) H₃O⁺

Question 26

What reagent(s) would you use for this reaction?

Answer 26

1) R-MgX

——————–>

2) H₃O⁺

Question 27

What reagent(s) would you use for this reaction?

Answer 27

MCPBA

Question 28

What reagent(s) would you use for this reaction?

Answer 28

X₂

(X= Br, Cl..)

Question 29

What reagent(s) would you use for this reaction?

Answer 29

CHBr₃

NaOH

Question 30

What does this result in?

Answer 30

Question 31

What is a reduction reaction?

Answer 31

Increased the number of bonds between carbon and hydrogen.

Decreased bonding to oxygen (or other more electroneg. atoms)

Question 32

What is an oxidation reaction?

Answer 32

Decrease in number of bonds between C and H

Increase in number of bonds to O or other EN atoms

Question 33

What are the limitations to Grignard Reagents?

(R-MgX)

Answer 33

they will attack carbonyls (C=O)

they will open epoxide rings

they will react with acidic H’s (O-H, N-H, *triple bond*CH)

Question 34

Which nucleophiles are kinetic?

(irreversible)

Answer 34

R^- : R-MgBr and R-L

H^- : NaBH₄ and LiAlH₄

Question 35

Which nucleophiles are thermodynamic?

(reversible)

Answer 35

HO^-, RO^-, Cl^-, Br^-, I^-, N*triple bond*C:^-