This document contains 25 multiple choice questions from a Chem 210 PSU exam 4. It tests concepts related to organic chemistry reactions, mechanisms, stereochemistry, and identifying structures and reagents. For each question, the correct multiple choice answer is provided.
This document contains 25 multiple choice questions from a Chem 210 PSU exam 4. It tests concepts related to organic chemistry reactions, mechanisms, stereochemistry, and identifying structures and reagents. For each question, the correct multiple choice answer is provided.
This document contains 25 multiple choice questions from a Chem 210 PSU exam 4. It tests concepts related to organic chemistry reactions, mechanisms, stereochemistry, and identifying structures and reagents. For each question, the correct multiple choice answer is provided.
This document contains 25 multiple choice questions from a Chem 210 PSU exam 4. It tests concepts related to organic chemistry reactions, mechanisms, stereochemistry, and identifying structures and reagents. For each question, the correct multiple choice answer is provided.
What is the second reagent used in the following conversion?
(a) NaNH2 (b) KMnO4 (c) BH3 (d) Br2 (e) HBr
Correct answer: A
What is the order of stability of the carbocations shown below? [Note A > B means that A is more stabilized than B.] (a) A > B > C (b) A > C > B (c) B > A > C (d) B > C > A (e) C > A > B (f) C > B > A
Correct answer: E
Which of the following compounds has the highest oxidation level?
Correct answer: ABCDE
Approximately, what is the yield of the chloride shown below obtained by
What is the expected order of reactivity of the following bromides in SN2 reactions? [Note A > B means that A reacts faster than B.] (a) A > B > C (b) A > C > B (c) B > A > C (d) B > C > A (e) C > A > B (f) C > B > A
Correct answer: E
What is the product of the following sequence of reactions?
Correct answer: D
For the following reaction, doubling the concentration of 1 has no effect on the reaction rate. Doubling the concentration of 2 has no effect on rate, but it decreases the yield of 5 and increases the yield of 4. What are the mechanisms at work? (a) SN1 and E1 (b) SN1 and E2 (c) SN2 and E1 (d) SN2 and E2 Correct answer: A
How many alkene products, including stereoisomers, might form in E1 elimination of the alcohol shown below? (a) 2 (b) 3 (c) 4 (d) 5 (e) 6
Correct answer: D
Which alkyl halide will yield only the product shown below in an E2 elimination process? [Hint: Draw the Newman projections or build models].
Correct answer: A
The reaction of methoxide (CH3O- ) with 2-bromobutane gives the substitution product shown below. Elimination products also form. Which structure represents the 2- bromobutane used as the reactant in this reaction?
Correct answer: E
Consider the following backside displacement reaction of (S)-(-)-1-iodo-2-methylbutane
(1) to produce (+)-2-methyl-1-butanol (2). What is the absolute configuration of the product? (a) R (b) S (c) R and S (racemic mixture) (d) R and S (unequal amounts)
Correct answer: B
How many constitutional isomers of the mono bromo product will form in the following reaction? (a) 1 (b) 2 (c) 3 (d) 4 (e) 5
Correct answer: C
What is the ΔHrxn (in kcal/mol) of the following reaction?
(a) -27 (b) -21 (c) -5 (d) 0 (e) 17 (f) 33
Correct answer: A
Based on the retrosynthetic analysis shown below, what is the reagent used in the first synthetic step of the preparation of the target molecule? [Hint: pay attention to stereochemistry.] (a) CH2I2/Zn(Cu) (b) Li/NH3(ℓ) (c) mCPBA (d) BH3; H2O2/NaOH (e) NaNH2 (f) H2/Lindlar Correct answer: B What is the expected order of reactivity of the following bromides in SN1 reaction? [Note A > B means that A reacts faster than B.] (a) A > B > C (b) A > C > B (c) B > A > C (d) B > C > A (e) C > A > B (f) C > B > A
Correct answer: F
The retrosynthetic analysis for synthesis of a deuterated (D = 2 H) substrate is sketched
below. What is the structure of the intermediate?
Correct answer: D
What is the outcome of the following reaction?
Correct answer: C Which bromide will not yield a persistent Grignard reagent upon treatment with Mg?
Correct answer: E
What is the order of stability for radicals shown below, starting with the most stable? (a) A > B > C (b) A > C > B (c) B > A > C (d) B > C > A (e) C > A > B (f) C > B > A
Correct answer: B
Which product cannot be made from phenylacetylene 1, in a "one-step" reaction? Note:
A "one-step" reaction includes all regents needed to finish the reaction, even if added stepwise (BH3; H2O2/NaOH, for example are consider one-step). Using a regent in excess also counts as one step reaction.
Correct answer: C
Which of the following SN2 reactions would be the fasted if run with the same concentrations of reactants and at the same temperature? Correct answer: B
The following transformation is carried out in three steps (I-III). What are the appropriate reagents for the third (III) step? (a) (CH3)2CuLi + (b) CH3I (c) PBr3 (d) H2/Pd (e) BH3; H2O2/NaOH
Correct answer: A
How many monochlorides formed in the following reaction are chiral?
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5
Correct answer: C
The radical chlorination of 1 gives 2 (among other products). What is true about the 1,2- dichlorocyclopetanes (2) formed? (a) two stereoisomers, one chiral (b) three stereoisomers, two chiral (c) three stereoisomers, one chiral (d) two stereoisomers, both achiral (e) three stereoisomers, all achiral
Correct answer: B Which compounds can serve as an immediate precursor in the synthesis of butanal, 1? Immediate precursor is a substance that can be converted into the target in one step. (a) A only (b) B only (c) C only (d) A and B (e) A and C (f) B and C (g) all three
