Quiz 2
- Page ID
- 10485
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)1. Give the best answer for the following multiple choice and labeling questions.
a) Which of the following will not react with a grignard reagent?
A) butyraldehyde
B) butan-2-one
C) 2-butanol
D) 1-butene
E) 1-butyne
b) The addition of a grignard reagent to a carbonyl is based on collision of a nucleophile to fill what acceptor orbital?
A) a s bonding orbital
B) a s* antibonding orbital
C) an empty p orbital
D) a p bonding orbital
E) a p* antibonding orbital
c) Which reactions will not give a product as a racemic mixture?
A) the addition of phenyl grignard to propionaldehyde
B) epoxidation of an allylic alcohol with a Ti(OiPr)4, tBuOOH, and (–)-diethyl tartrate
C) the addition of NaOCH3 to cyclohexene oxide
D) the acid-catalyzed addition of methanol to cyclohexene oxide
E) an SN1 reaction
d) Which of the following is not a true statement:
A) a silyl ether bond can be cleaved by a fluoride source, such as TBAF
B) LiAlH4 is an oxidizing agent
C) epoxide formation using mCPBA with an alkene proceeds via a concerted mechanism
D) H2CrO4 will oxidize a secondary alcohol to a ketone
E) arene oxides can react with DNA and initiate cancer-causing pathways
e) In the boxes provided, indicate whether each of the following reactive carbon atoms is considered to be electrophilic (E) or nucleophilic (N). R is used to indicate either H or alkyl.
2. Draw the resonance contributor for a ketone, showing any curved arrows for its formation. Briefly explain what this resonance indicates about the reactivity of a carbonyl.
3. Ethylene oxide is the starting material for the synthesis of “Cellosolve”, an important industrial solvent. Provide a curved arrow mechanism for this reaction.
4. Provide a curved arrow mechanism for the following transformation.
5. Synthesis
a) Show how to synthesize the following alcohol where all carbons in the molecule must come from compounds with 3 or fewer carbon atoms. Include all necessary reagents for the synthesis you propose.
b) Explain why you would need to use a protecting group strategy in a synthesis and give an example of a synthesis that requires the use of a protecting group. Your synthesis must have at least 3 steps to receive full credit.
6. An aziridinium ion follows a similar reactivity pattern to an epoxide. The following aziridinium ion reacts with NaOCH3 to form compounds A and B. Given what you know about the reactivity patterns of epoxides and the information given below, identify the structures of both compounds A and B (in boxes provided).
