Organic Chemistry Test 3 Flashcards
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Questions and Answers

In an addition reaction to an alkene, the π bond is ______.

a nucleophile

Addition reactions of alkenes are characterized by _________.

  • Only addition of one group across a double bond
  • Addition of two groups across a double bond (correct)
  • No reaction
  • Breaking of a π bond (correct)
  • Most π bonds are quite prone to reaction with an ____________________, also referred to as electron-seeking reagents.

    electrophilic

    The alkene precursor to ethanol is __________.

    <p>ethylene or ethene</p> Signup and view all the answers

    For an addition reaction, why does free energy, ∆G, become more positive with increasing temperature?

    <p>The negative entropy dominates at high temperature.</p> Signup and view all the answers

    Describe the regioselectivity and stereospecificity in the hydrohalogenation of an alkene.

    <p>Markovnikov orientation with both syn- and anti-addition.</p> Signup and view all the answers

    Give the best description of the regioselectivity and stereospecificity in the oxymercuration of an alkene.

    <p>Markovnikov orientation with anti-addition.</p> Signup and view all the answers

    What are the products of the reaction CH3OH + CH3C≡CNa+ → ?

    <p>CH3C≡CH + CH3ONa+</p> Signup and view all the answers

    A dihalide in which the halogens are attached on adjacent carbons is called a _______________ dihalide.

    <p>vicinal</p> Signup and view all the answers

    A dihalide in which the halogens are attached on the same carbon is called a _______________ dihalide.

    <p>geminal</p> Signup and view all the answers

    For the reaction shown, select the expected major product.

    <p>IV</p> Signup and view all the answers

    Rank the following hydrocarbons in order of decreasing acidity (most acidic to least acidic).

    <p>III &gt; II &gt; I</p> Signup and view all the answers

    ID major product.

    Signup and view all the answers

    For the reaction shown, select the expected major organic product.

    <p>III</p> Signup and view all the answers

    Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?

    <p>III</p> Signup and view all the answers

    For the reaction below, select the structure of the expected major organic product.

    <p>III</p> Signup and view all the answers

    Identify the best reagent(s) for this reaction.

    <p>H2SO4, HgSO4, H2O</p> Signup and view all the answers

    Identify the best reagent(s) for this reaction.

    <ol> <li>Disiamylborane, 2. HO-, H2O2</li> </ol> Signup and view all the answers

    Identify the final product for the following reaction.

    <p>II</p> Signup and view all the answers

    Identify the final product for the following reaction.

    <p>III</p> Signup and view all the answers

    For the reaction shown, which of the compounds listed below would be the expected major, and final, organic product?

    <p>IV</p> Signup and view all the answers

    Identify the functional group that would be expected to be found in the final product in the reaction below.

    <p>aldehyde</p> Signup and view all the answers

    Give the expected major product of the following reaction.

    <p>IV</p> Signup and view all the answers

    Identify the expected major product of the following reaction.

    <p>III</p> Signup and view all the answers

    The three compounds below can form a carbocation under aqueous acidic conditions. Which ones will form the same carbocation?

    <p>all three</p> Signup and view all the answers

    What would be the optimal conditions to effect the following synthesis?

    <p>concentrated H2SO4</p> Signup and view all the answers

    What would be the optimal conditions to effect the following synthesis?

    <p>dilute aqueous H2SO4</p> Signup and view all the answers

    Which of the following is the major product of the reaction shown?

    <p>IV</p> Signup and view all the answers

    Describe the products of the reaction below.

    <p>an equal mixture of enantiomers</p> Signup and view all the answers

    What is the expected major product for the following reaction?

    <p>II</p> Signup and view all the answers

    Study Notes

    Addition Reactions of Alkenes

    • In addition reactions, the π bond of alkenes acts as a nucleophile and is broken.
    • Addition reactions involve the addition of two groups across a double bond and the breaking of a π bond.

    Electrophiles and Alkenes

    • π bonds commonly react with electrophiles, which are electron-seeking reagents.

    Alkene Precursors

    • Ethylene (or ethene) serves as the alkene precursor to ethanol.

    Free Energy and Temperature

    • During addition reactions, free energy (∆G) becomes more positive at higher temperatures due to the dominance of negative entropy.

    Hydrohalogenation Specificity

    • Hydrohalogenation shows Markovnikov orientation, resulting in both syn- and anti-addition, which affects regioselectivity and stereospecificity.

    Oxymercuration Specificity

    • Oxymercuration also follows Markovnikov orientation but exclusively exhibits anti-addition.

    Reaction Products

    • Reaction of methanol (CH3OH) with sodium acetylide (CH3C≡CNa+) yields propyne (CH3C≡CH) and sodium methoxide (CH3ONa+).

    Dihalides Classification

    • A vicinal dihalide has halogens attached to adjacent carbons, while a geminal dihalide features halogens on the same carbon atom.

    Acidity Ranking

    • Hydrocarbons ranked by decreasing acidity: III > II > I.

    Major Products

    • For various reactions, identifying the expected major organic product frequently results in compounds designated as II, III, and IV.

    Reagents for Reactions

    • Common reagents include H2SO4, HgSO4, and H2O.
    • For specific reactions, disiamylborane followed by HO- and H2O2 is also used.

    Functional Groups and Final Products

    • In reactions producing aldehydes, the expected functional group found in the final product is an aldehyde.
    • The final products of specific reactions can often be identified as an equal mixture of enantiomers.

    Synthesis Conditions

    • Concentrated and dilute aqueous H2SO4 present optimal conditions for effecting certain syntheses.

    Carbocations Formation

    • Several compounds can form the same carbocation under aqueous acidic conditions, with all three mentioned compounds being included.

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    Description

    Test your knowledge on addition reactions of alkenes with this Organic Chemistry Test 3 flashcard set. Each card highlights key concepts such as nucleophiles and electrophilic reagents. Perfect for reviewing important terminologies and definitions in organic chemistry.

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