8+ cat.NaOH H3C一HH3C-CH21 OH CHa OH HC-HC-C-CH-
Page 1 1. Which product would you not expect in the crossed aldol reaction between acetaldehyde and propionaldehyde? H3C C O H CH2 C O H3C H ? cat. NaOH H2O + A) CH2 C O H H2C C OH H H3C B) CH C O H H3C C CH3 H OH C) CH2 C O H H3C C OH H D) CH C O H H3C C OH H CH3 E) CH C O H H2C C OH H CH3 H3C Ans: B
2.What organic molecule would you expect to be present in significant amounts under the following conditions? only(S)enantiome c Page2
Page 2 2. What organic molecule would you expect to be present in significant amounts under the following conditions? O CH3 H cat. KOD ? only (S) enantiomer excess D2O A) DO CH3 H OH B) O CH3 D C) O D) O CH3 D racemic E) O CD3 D racemic Ans: D
What reactants would be used to produce cinnamaldehyde H,0 Page 3
Page 3 3. What reactants would be used to produce cinnamaldehyde? CHO ? cat. NaOH H2O A) CHO + CH3CHO B) CHO H C CHO O + C) CH3 O + CH2=O D) O CHO + E) CHO H3C C CHO O + Ans: A
What would you expect to result from the following reaction? 1.(CH3)2CuLi 2.H20 C) D) Page 4
Page 4 4. What would you expect to result from the following reaction? O ? 1. (CH3)2CuLi 2. H2O A) O B) OH C) OH CH3 D) O E) O Ans: A
5.Indicate to which side,if any,the following equilibrium lies H'or HO D erpa Major product is an enol or enolate ion,respectively Ans: Page
Page 5 5. Indicate to which side, if any, the following equilibrium lies: O O H+ or HOA) To the right B) To the left C) Equally to right and left D) Cannot be predicted E) Major product is an enol or enolate ion, respectively Ans: A
What would be the expected product of the following reaction C. CH,OH heat c) Page 6
Page 6 6. What would be the expected product of the following reaction? CH3 O HC CH2 O + CH3 CH3O- Na+ CH3OH ? heat A) O B) O C) O D) O E) O Ans: A
7.What major product would you expect from the following reaction? CH2-0 CHOH,hea Ans 8.Which proton in the following molecule is the most acidic? CH2-CH2-0 B)2 C)3 D E) D Page 7
Page 7 7. What major product would you expect from the following reaction? O Na+ -OCH3 CH3OH, heat ? CH2=O A) HO OCH3 B) CH2 C) O CH3 D) CH2 O E) O Ans: D 8. Which proton in the following molecule is the most acidic? CH2 CH2 C O H H H 2 5 3 4 1 A) 1 B) 2 C) 3 D) 4 E) 5 Ans: D
9.What product is formed in the aldol condensation of propanal? KOH CHCH>CHO H,0 CHO CHO Ans:B 10.To which side,if any,would the following equilibrium lie? OH HC-C=cHz H-C-C-CH3 Tote en Reaction cannot occur at all To the right Equilibrium favors a different product. C)Equally to the left and right Ans:B Page8
Page 8 9. What product is formed in the aldol condensation of propanal? CH3CH2CHO KOH H2O ? A) CHO O B) CHO OH C) OH O D) HO CHO E) CHO OH Ans: B 10. To which side, if any, would the following equilibrium lie? H3C C O H3C CH3 C OH CH2 A) To the left D) Reaction cannot occur at all B) To the right E) Equilibrium favors a different product. C) Equally to the left and right Ans: B
1.To which side,if any,would the following equilibrium lie? o-Na* HC-C=CH2 +H,0之 NaOH HC一CCH3 C)Equally to the left and right Ans:B Page9
Page 9 11. To which side, if any, would the following equilibrium lie? H3C C O H3C CH3 C O CH2 + H2O - Na+ + NaOH A) To the left D) Reaction cannot occur at all B) To the right E) Equilibrium favors a different product. C) Equally to the left and right Ans: B
12eemgegeawaehaentgaeakw NaOCH2CH3_H;O* 3 Page 10
Page 10 12. Which major product would you expect when the following diketone undergoes aldol cyclization in base, followed by acid? O O NaOCH2CH3 H3O+ A) O H3C B) O O C) CH3 O CH3 D) O CH3 E) O CH3 Ans: A
