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Embed code for: Ochem 328 SI 12 Exam 2 Review
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Organic Chemistry 328 SI
Exam Review 2
3.14 (Happy pi day!) <3
39 Practice Questions
Exam 2 Breakdown
Chapter 18 (last half) – Chapter 21 (first half)
Be able to use old reagents
What is the approximate pKa of propionic acid?
2-Pentanone is mixed with (R) CBS – Reagent, then H2O, which product forms?
(I emailed Dr. Halaweish with a question on this one, I will update Facebook if he responds with a different answer)
Starting with a benzene, which reagent sequence will form these products?
 CH3CH2COCl / AlCl3  Zn, HCl  HNO3 /H2SO4  Cl2 / FeCl3
 HNO3 /H2SO4  CH3CH2CH2Cl / AlCl3  Cl2 / FeCl3
 CH3CH2COCl / AlCl3  Cl2 / FeCl3  NH2NH2, -OH  HNO3 /H2SO4
What reagent sequence completes this reaction?
 Mg  CO2  H3O+
 2 Li  Formaldehyde  H2O  CrO3 / H2SO4
 MeMgBr  H2O  KMnO4
I and II
What is the product?
A mixture of 1-hexanol, hexanoic acid and CH2Cl2 is mixed with aqueous sodium bicarbonate and shaken. How do the molecules separate?
CH2Cl2 Layer Aqueous Layer
1-hexanol hexanoic acid
1-hexanol sodium hexanoate
hexanoic acid sodium 1-hexanoxide
Sodium hexanoate 1-hexanol
Trick question, they are both in the organic (CH2Cl2) layer since they are not water soluble.
What reagents complete this reaction?
 CH3Li (2 eq)  H2O
 CH3MgCl (2 eq)  H2O
 (CH3)2CuLi (2 eq)  H2O
Only A and B
All of the above
IV and the minor product
Which of these indicate the correct order of decreasing acidity?
CH3CH2OH > FCH2COOH > ClCH2COOH
ICH2COOH > ClCH2COOH > FCH2COOH
Cl2CHCOOH > ClCH2COOH > CH3COOH
CH3COOH > FCH2COOH > CH3CH2OH
Under harsh conditions, what is the product?
 CH3CH2COCl / AlCl3
 Hg, HCl / ∆  KMnO4
Place these molecules in order of increasing reactivity
1 < 2 < 3
1 < 3 < 1
2 < 3 < 1
3 < 2 < 1
III and CO2
What reagent sequence forms this product?
 ClMgEt  H2O
 BrMgCH2CHOHCH3  H2O
 TBAF  ClMgEt  H2O  Cl-TMBS
 Cl-TMBS  ClMgEt  H2O  TBAF
III and IV
 H2 / Pd-C  PCC
LiAlH4  H2O
H2 (excess) / Pd-C
 NaBH4  CH3OOH
All except for A
Which reagent produces this product?
 H2O2, -OH
II and CO2
 BrMgCH3 (ex)
At a high concentration of –OH, what is the charge on alanine?
What are the products?
 Zn, H2O
I and IV
II and III
During an Elimination-Addition, what intermediate forms?
Name this compound.
 CH3CClCH2CH2CH3 / / AlCl3
What are the products of the oxidative cleavage of 1-hexyne?
Valeric acid and formic acid
Pentanoic acid and methanoic acid
Valeric acid and carbon dioxide
Hexanoic acid and formic acid
What are the products of the oxidative cleavage of this molecule? (Use the common name)
2-methylpropanoic acid and 3-methylpentoic acid
α-methylpropionoic acid and β-methylvaleric acid
2-methylpropanoic acid and 3-methylvaleric acid
α-methylpropanoic acid and β-methylpentoic acid
Place these molecules in order of increasing reactivity with NaOCH2CH3.
I < II < III ≈ IV
II < I < III ≈ IV
III < IV < I < II
II < I < IV < III
Which shows the molecules in order of decreasing acidity?
FCH2COOH > ClCH2COOH > BrCH2COOH
CH3COOH > ClCH2COOH > Cl2CHCOOH
What is the product of a reaction between acetophenone, Lithium aluminum Hydride and water?