Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 20, Problem 20.29P
What organocuprate reagent is needed to convert
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each one of the following questions:
a) The bond length of the Br2 molecule is 2.28 Å, while the bond length of the compound KBr is 3.34 Å. The radius of
K✶ is 1.52 Å. Determine the atomic radius in Å of the bromine atom and of the bromide ion.
Br =
Br
b) Explain why there is a large difference in the atomic sizes or radius of the two (Br and Br).
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When 15.00 mL of 3.00 M NaOH was mixed in a calorimeter with 12.80 mL of 3.00 M HCl, both initially at room temperature (22.00 C), the temperature increased to 29.30 C. The resultant salt solution had a mass of 27.80 g and a specific heat capacity of 3.74 J/Kg. What is heat capacity of the calorimeter (in J/C)? Note: The molar enthalpy of neutralization per mole of HCl is -55.84 kJ/mol.
Chapter 20 Solutions
Organic Chemistry-Package(Custom)
Ch. 20 - Prob. 20.1PCh. 20 - Which carbonyl groups in the anticancer drug taxol...Ch. 20 - Prob. 20.3PCh. 20 - Prob. 20.4PCh. 20 - Problem 20.5 What aldehyde or ketone is needed to...Ch. 20 - Prob. 20.6PCh. 20 - Problem 20.7 Draw the products formed when is...Ch. 20 - Prob. 20.8PCh. 20 - Prob. 20.9PCh. 20 - Prob. 20.10P
Ch. 20 - Draw the structure of both an acid chloride and an...Ch. 20 - Problem 20.12 Draw the products formed from ...Ch. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - What product is formed when...Ch. 20 - Prob. 20.16PCh. 20 - Problem-20.16 Review the oxidation reactions using...Ch. 20 - Problem-20.17 Write the step(s) needed to convert ...Ch. 20 - Problem-20.18 Oct-1-yne reacts rapidly with ,...Ch. 20 - Draw the product formed when each organometallic...Ch. 20 - Draw the product of each reaction. a.c. b.d.Ch. 20 - Draw the products including stereochemistry of the...Ch. 20 - What Grignard reagent and carbonyl compound are...Ch. 20 - Problem 20.24 Linalool (the Chapter 9 opening...Ch. 20 - Problem 20.25 What Grignard reagent and carbonyl...Ch. 20 - Prob. 20.26PCh. 20 - Draw the products formed when each compound is...Ch. 20 - What ester and Grignard reagent are needed to...Ch. 20 - What organocuprate reagent is needed to convert...Ch. 20 - What reagent is needed to convert (CH3)2CHCH2CHO...Ch. 20 - Prob. 20.31PCh. 20 - What carboxylic acid formed from each alkyl halide...Ch. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - Problem 20.35 Synthesize each compound from...Ch. 20 - Prob. 20.36PCh. 20 - 20.37 Devise a synthesis of each alcohol from...Ch. 20 - 20.38 Draw the products formed when pentanal is...Ch. 20 - Prob. 20.39PCh. 20 - Draw the product formed when CH3CH2CH2MgBr is...Ch. 20 - Draw the product formed when (CH3CH2CH2CH2)2CuLi...Ch. 20 - The stereochemistry of the products of reduction...Ch. 20 - Prob. 20.43PCh. 20 - What reagent is needed to convert...Ch. 20 - What reagent is needed to convert...Ch. 20 - Draw the products or each reduction reaction. a....Ch. 20 - Prob. 20.47PCh. 20 - Draw all stereoisomers formed in each reaction. a....Ch. 20 - Prob. 20.49PCh. 20 - 20.46 Treatment of ketone A with ethynylithium...Ch. 20 - 20.47 Explain why metal hydride reduction gives an...Ch. 20 - Prob. 20.52PCh. 20 - 20.49 Identify the lettered compounds in the...Ch. 20 - Prob. 20.54PCh. 20 - Draw a stepwise mechanism for each reaction. a. b.Ch. 20 - Prob. 20.56PCh. 20 - 20.54 Draw a stepwise mechanism for the following...Ch. 20 - What Grignard reagent and aldehyde or ketone are...Ch. 20 - Prob. 20.59PCh. 20 - What ester and Grignard reagent are needed to...Ch. 20 - What organolithium reagent and carbonyl compound...Ch. 20 - 20.59 What epoxide and organometallic reagent are...Ch. 20 - Prob. 20.63PCh. 20 - 20.61 Propose two different methods to synthesize...Ch. 20 - Synthesize each compound from cyclohexanol using...Ch. 20 - Prob. 20.66PCh. 20 - Prob. 20.67PCh. 20 - Devise three different methods to prepare each...Ch. 20 - Convert benzene into each compound. You may also...Ch. 20 - Design a synthesis of each compound from alcohols...Ch. 20 - Synthesize each compound from the given starting...Ch. 20 - 20.69 An unknown compound A (molecular formula )...Ch. 20 - 20.70 Treatment of compound C (molecular formula )...Ch. 20 - 20.71 Treatment of compound E (molecular formula )...Ch. 20 - 20.72 Reaction of butanenitrile () with methyl...Ch. 20 - 20.73 Treatment of isobutene with forms a...Ch. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - 20.76 Lithium tri-sec-butylborohydride, also known...Ch. 20 - Prob. 20.80PCh. 20 - Prob. 20.81PCh. 20 - Prob. 20.82PCh. 20 - 20.80 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.84P
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- When 15.00 mL of 3.00 M NaOH was mixed in a calorimeter with 12.80 mL of 3.00 M HCl, both initially at room temperature (22.00 C), the temperature increased to 29.30 C. The resultant salt solution had a mass of 27.80 g and a specific heat capacity of 3.74 J/Kg. What is heat capacity of the calorimeter (in J/C)? Note: The molar enthalpy of neutralization per mole of HCl is -55.84 kJ/mol. Which experimental number must be initialled by the Lab TA for the first run of Part 1 of the experiment? a) the heat capacity of the calorimeter b) Mass of sample c) Ti d) The molarity of the HCl e) Tfarrow_forwardPredict products for the Following organic rxn/s by writing the structurels of the correct products. Write above the line provided" your answer D2 ①CH3(CH2) 5 CH3 + D₂ (adequate)" + 2 mited) 19 Spark Spark por every item. 4 CH 3 11 3 CH 3 (CH2) 4 C-H + CH3OH CH2 CH3 + CH3 CH2OH 0 CH3 fou + KMnDy→ C43 + 2 KMn Dy→→ C-OH ") 0 C-OH 1110 (4.) 9+3 =C CH3 + HNO 3 0 + Heat> + CH3 C-OH + Heat CH2CH3 - 3 2 + D Heat H 3 CH 3 CH₂ CH₂ C = CH + 2 H₂ → 2 2arrow_forwardWhen 15.00 mL of 3.00 M NaOH was mixed in a calorimeter with 12.80 mL of 3.00 M HCl, both initially at room temperature (22.00 C), the temperature increased to 29.30 C. The resultant salt solution had a mass of 27.80 g and a specific heat capacity of 3.74 J/Kg. What is heat capacity of the calorimeter (in J/C)? Note: The molar enthalpy of neutralization per mole of HCl is -55.84 kJ/mol.arrow_forward
- Q6: Using acetic acid as the acid, write the balanced chemical equation for the protonation of the two bases shown (on the -NH2). Include curved arrows to show the mechanism. O₂N- O₂N. -NH2 -NH2 a) Which of the two Bronsted bases above is the stronger base? Why? b) Identify the conjugate acids and conjugate bases for the reactants. c) Identify the Lewis acids and bases in the reactions.arrow_forwardQ5: For the two reactions below: a) Use curved electron-pushing arrows to show the mechanism for the reaction in the forward direction. Redraw the compounds to explicitly illustrate all bonds that are broken and all bonds that are formed. b) Label Bronsted acids and bases in the left side of the reactions. c) For reaction A, which anionic species is the weakest base? Which neutral compound is the stronger acid? Is the forward or reverse reaction favored? d) Label Lewis acids and bases, nucleophiles and electrophiles in the left side of the reactions. A. 용 CH3OH я хон CH3O OH B. HBr CH3ONa NaBr CH3OHarrow_forwardpotential energy Br b) Translate the Newman projection below to its wedge-and-dash drawing. F H. OH CH3 CI c) Isopentane (2-methylbutane) is a compound containing a branched carbon chain. Draw a Newman projection of six conformations about the C2-C3 bond of isopentane. On the curve of potential energy versus angle of internal rotation for isopentane, label each energy maximum and minimum with one of the conformations. 0° 。 F A B D C angle of internal rotation E F 360° (=0°) JDownlarrow_forward
- Q7: Identify the functional groups in these molecules a) CH 3 b) Aspirin: HO 'N' Capsaicin HO O CH3 CH 3arrow_forwardQ2: Name the following alkanesarrow_forward1. Complete the following table in your laboratory notebook. Substance Formula Methanol CH3OH Ethanol C2H5OH 1-Propanol C3H7OH 1-Butanol C4H9OH Pentane C5H12 Hexane C6H14 Water H₂O Acetone C3H60 Structural Formula Molecular Weight (g/mol) Hydrogen Bond (Yes or No)arrow_forward
- Q1: Compare the relative acidity in each pair of compounds. Briefly explain. (a) CH3OH vs NH 3 (b) HF vs CH3COOH (c) NH3 vs CH4 (d) HCI vs HI (e) CH3COOH vs CH3SH (f) H₂C=CH2 vs CH3 CH3 (g) compare the acidity of the two bolded hydrogens O. H N- (h) compare the acidity of the two bolded hydrogens, draw resonance structures to explain H H Harrow_forwardQ3: Rank the following molecules in order of decreasing boiling point: (a) 3-methylheptane; (b) octane; (c) 2,4-dimethylhexane; (d) 2,2,4-trimethylpentane.arrow_forwardQ5: Conformations of Alkanes a) Draw a Newman Projection of the compound below about the C2-C3 bond. H3C Cli... H IIIH Br CH3arrow_forward
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