135A_Practice_EXAM_4(Karty3e)_KEY(1)

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Chemistry

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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
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?
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