135A_Practice_EXAM_4(Karty3e)_KEY(1)

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Dec 6, 2023

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CHEM 135-A Practice Test for Exam 4 (Karty3e) KEY 1. (10 pt) How many signals would you expect in the 1 H NMR and in the 13 C NMR spectra of the following compounds. # signals in H NMR # signals in 13 C NMR
2. (30 pt) Draw the principal organic product(s) expected from the following reactions.
3. (5 pts) Arrange the compounds below in order of INCREASING reactivity toward toward nucleophilic acyl addition. ____ B ______ < _____ D ____ < _____ C ____ < _____ A _____ Least Reactive Most Reactive 4. (5 pts) Arrange the compounds below in order of INCREASING chemical shift in the H NMR spectrum. ____ D _____ < ____ A _____ < ____ C _____ < ____ B ______ Smallest Largest 5. (40 pts) Circle ONE answer for each of the following ten multiple choice questions. a. Which of the following reagents will transform hexanenitrile to 1-hexanamine? (A) NaBH 4 (B) LiAlH 4 (C) LDA (D) NaBH 3 CN b. What set of alkyl halide (1) and carbonyl compound (2) will provide 2-methyl-2-pentene when submitted to the reaction conditions shown? (A)1-bromobutane and acetone (B) 1-bromopropane and acetone (C) 2-bromopropane and butanal (D) 2-bromopropane and ethanol c. What products are produced when the cyclic compound shown is hydrolyzed in aqueous
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acid? d. CIRCLE the letter that corresponds to the carbon atom that appears the furthest DOWNFIELD in the C13-NMR spectrum? e. What starting material will NOT result in formation of the alcohol shown when it’s reacted with phenylmagnesium bromide followed by an acid work-up? (A)Butanoic acid (B) Butanoyl chloride (C) Methyl butanoate (D)Butanoic anhydride f. What products are obtained from the following sequence of reactions.
g. What is the major product of this reaction? h. What is the product formed in the following reaction?
i. Which carboxyl group will be readily lost as carbon dioxide when the steroid tetracarboxylic acid shown is heated? O CO 2 H HO 2 C CO 2 H CO 2 H 2 5 15 13 (A) CO 2 H at C-15 (B) CO 2 H at C-13 (C) CO 2 H at C-5 (D) CO 2 H at C-2 j. What product is expected when benzonitrile is treated with methyl magnesium bromide? k. What would be the product of the reaction shown below?
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l. What product is formed in the reaction shown below? m. Predict the product of the following Wittig reaction. n. Which of the following compounds is NOT an intermediate in the acid-catalyzed hydrolysis of the acetal shown?
o. What product is expected from the reaction shown? p. What cyclic compound is expected to form when the diketone shown is treated with base followed by heating in acidic solution? q. Identify the alkyl halide that could be used to synthesize 5-methyl-2-hexanone from ethyl acetoacetate as shown in the sequence below.
r. What reducing agent should be used to carry out this transformation? (A) NaBH 4 (B) LiAlH 4 (C) LTBA (lithium tri- tert -butoxyaluminum hydride) (D) DIBAH (diisobutylaluminum hydride) s. Which of the following is NOT an intermediate formed when 2-cyclohexenone reacts with HCl to form 3-chlorohexanone? t. What product is formed in the following reaction?
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6. (5 pts) Select the compounds that would produce ONLY two doublet signals in their H NMR spectrum. 7. (5 pts) An unknown compound with molecular formula C 8 H 10 O produces the IR and NMR spectra shown below. Write the structure of the compound that is consistent with the spectroscopic data. Infrared Spectrum of Unknow n
Proton NMR Spectrum of Unknown Enlargement of H NMR (2 – 5 ppm) C13 NMR spectrum
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