Lecture23Final(10)

Lecture23Final(10) - Organic Chemistry, Third Edition...

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1 Organic Chemistry, Third Edition Janice Gorzynski Smith University of Hawai’i Chapter 10 Alkenes
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2 What is/are the major organic product of the following reaction ? C C CH 3 + BrCH 2 ? C C BrCH 2 CH 2 C CH CH 3 + CH 3 C C CH 3 CH 2 C C CH 3 Br C C CH 2 CH 2 A. B. C. D. E. !
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3 What is the most likely mechanism of this reaction? A) S N 1 B) S N 2 ! C) E1 D) E2 E) None of the choices is correct.
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4 Which of the labeled protons in compound A is most readily abstracted under conditions of E2 elimination? A) H a B) H b C) H c D) H d E) H e !
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5 A tertiary alkyl halide reacts with a weak base, which is also a weak nucleophile. The reaction will proceed via which of the following mechanism(s)? A) S N 1 B) S N 2 C) E1 D) E2 E) S N 1 and E1 !
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6 Which of the following alkyl halides reacts the fastest in an E2 reaction? !
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7 Predict the E2 product(s) formed when ( 1S, 2S )-1-bromo-1,2- diphenylpropane reacts with NaOCH 3 . !
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8 Alkenes are also called olefins . Alkenes contain a carbon-carbon double bond. Terminal alkenes have the double bond at the end of the carbon chain. Internal alkenes have at least one carbon atom bonded to each end of the double bond. Cycloalkenes contain a double bond in a ring. Alkene Structure
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9 Recall that the double bond consists of a ! bond and a " bond. Each carbon is sp 2 hybridized and trigonal planar, with bond angles of approximately 120°. Alkene Hybridization
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Structure of alkene
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Bond dissociation energies of the C–C bonds in ethane (a " bond only) and ethylene (one " and one ! bond) can be used to estimate the strength of the ! component of the double bond. The ! bond is much weaker than the " bond of a C–C double bond; it is much more easy to break. Therefore, alkenes undergo many reactions than alkanes .
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Lecture23Final(10) - Organic Chemistry, Third Edition...

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