PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Author: SMITH
Publisher: MCG
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Chapter 20, Problem 20.25P
What Grignard reagent and carbonyl compound can be used to prepare the antidepressant venlafaxine (trade name Effexor)?
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Q5. Predict the organic product(s) for the following transformations. If no reaction will take place
(or the reaction is not synthetically useful), write "N.R.". Determine what type of transition state
is present for each reaction (think Hammond Postulate).
I
Br₂
CH3
F2, light
CH3
Heat
CH3
F₂
Heat
Br2, light
12, light
CH3
Cl2, light
a. For the following indicated bonds, rank them in order of decreasing AH° for homolytic
cleavage. Based on your answer, which bond would be most likely to break homolytically?
(a)
(c)
H3C
CH3
.CH3
CH3
CH3
(b)
Page 1 of 5
Chem 0310 Organic Chemistry 1 Recitations
b. Draw all the possible radical products for 2-methylbutane, and determine which bond is most
likely to be broken.
A 5-m³ rigid tank contains 5 kg of water at 100°C. Determine (a) the pressure, (b) the total
enthalpy, and (c) the mass of each phase of water.
Chapter 20 Solutions
PKG ORGANIC CHEMISTRY
Ch. 20 - Prob. 20.1PCh. 20 - Which carbonyl groups in the anticancer drug taxol...Ch. 20 - Prob. 20.3PCh. 20 - Problem 20.4 What alcohol is formed when each...Ch. 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 - Problem 20.8 Draw the products formed (including...Ch. 20 - Prob. 20.9PCh. 20 - Problem 20.10 Draw a stepwise mechanism for the...
Ch. 20 - Prob. 20.11PCh. 20 - Problem 20.12 Draw the products formed from ...Ch. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - Prob. 20.15PCh. 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 - Prob. 20.19PCh. 20 - Prob. 20.20PCh. 20 - Problem 20.21 Draw the product of each reaction.
...Ch. 20 - Problem 20.22 Draw the products (including...Ch. 20 - Problem 20.23 What Grignard reagent and carbonyl...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 - Problem 20.28 What ester and Grignard reagent are...Ch. 20 - Prob. 20.29PCh. 20 - Problem 20.30 What reagent is needed to convert ...Ch. 20 - Prob. 20.31PCh. 20 - What carboxylic acid formed from each alkyl halide...Ch. 20 - Prob. 20.33PCh. 20 - Problem 20.34 Draw the product when each compound...Ch. 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 - 20.39 Draw the product formed when is treated...Ch. 20 - The stereochemistry of the products of reduction...Ch. 20 - Prob. 20.41PCh. 20 - 20.42 Draw the products or each reduction...Ch. 20 - Prob. 20.43PCh. 20 - 20.44 Draw all stereoisomers formed in each...Ch. 20 - Prob. 20.45PCh. 20 - 20.46 Treatment of ketone A with ethynylithium...Ch. 20 - 20.47 Explain why metal hydride reduction gives an...Ch. 20 - Prob. 20.48PCh. 20 - 20.49 Identify the lettered compounds in the...Ch. 20 - Prob. 20.50PCh. 20 - 20.51 Draw a stepwise mechanism for the following...Ch. 20 - 20.52 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.53PCh. 20 - 20.54 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.55PCh. 20 - Prob. 20.56PCh. 20 - 20.57 What ester and Grignard reagent are needed...Ch. 20 - 20.58 What organolithium reagent and carbonyl...Ch. 20 - 20.59 What epoxide and organometallic reagent are...Ch. 20 - Prob. 20.60PCh. 20 - 20.61 Propose two different methods to synthesize...Ch. 20 - 20.62 Synthesize each compound from cyclohexanol...Ch. 20 - 20.63 Convert propan-2-ol into each compound....Ch. 20 - 20.64 Convert benzene into each compound. You may...Ch. 20 - 20.65 Design a synthesis of each compound from...Ch. 20 - 20.66 Synthesize each compound from the given...Ch. 20 - Prob. 20.67PCh. 20 - Prob. 20.68PCh. 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 - 20.74 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.75PCh. 20 - 20.76 Lithium tri-sec-butylborohydride, also known...Ch. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - Prob. 20.79PCh. 20 - 20.80 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.81P
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- Q8. Draw the mechanism for this halogenation reaction. Show all steps including initiation, propagation, and recombination. Cl₂, hv CI Br Br2, hv, heatarrow_forwardQ6. Given the following alkanes, draw the most likely product to form upon monohalogenation with Br2 (keep in mind that this may not be the only product to form though). If the reaction was performed with Cl2 would there be more or less selectivity in the desired product formation? Why? (a) (b) (c)arrow_forwardQ4. Radicals a. For the following indicated bonds, rank them in order of decreasing AH° for homolytic cleavage. Based on your answer, which bond would be most likely to break homolytically? (c) CH3 CH3 H3C CH3 (a) CH3 (b)arrow_forward
- Q1. (a) Draw equations for homolytic and heterolytic cleavages of the N-H bond in NH3. Use curved arrows to show the electron movement. (b) Draw equations for homolytic and heterolytic cleavages of the N-H bond in NH4*. Use curved arrows to show the electron movement.arrow_forwardohing Quantitative Relationships 425 The specific heats and atomic masses of 20 of the elements are given in the table below. Use a graphical method to determine if there is a relationship between specific heat and the atomic mass. a. b. C. d. e. If your graphs revealed relationship between specific heat and atomic revealed a mathematical mass, write down an equation for the relationship. Comment on the usefulness of the determination of specific heat as a method for identifying an element. Would specific heat alone give you much confidence with regard to the identity of the element? If you think measurement of another property would be needed to support an identification, what property would you measure and why? The elements listed in the table are all selected metals. The values for nitrogen, oxygen, fluorine and neon are 1.040, 0.918, 0.824 and 1.030 J/g K respectively. Do these elements fit your equation? element atomic mass specific heat (almol) (Jig K) magnesium 24.305 1.023…arrow_forwardPlease correct answer and don't use hand rating and don't use Ai solutionarrow_forward
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