FA23-PS07-Chapter6 KEY-1 (1)

pdf

School

University of California, San Diego *

*We aren’t endorsed by this school

Course

40A

Subject

Chemistry

Date

Jan 9, 2024

Type

pdf

Pages

Uploaded by MinisterBookSnail3

CHEM 40A Fall 2023 ©2023 Dept. of Chemistry & Biochemistry . Do not copy or distribute without permission. PS 7 Chapter 6 Overview of Organic Reactivity 15 Points Possible Please provide answers for the following questions within the provided boxes to receive credit. Only answers inside of boxes will be viewed and scored. Name:_____________________________ PID:_______________________________ Exercises 1. A proton transfer reaction can involve a positively charged substance as the source of the proton. a. This is the structure of protonated methanol. Consider all bonds involving hydrogen atoms , and label those that is/are polar using the partial charge notation described in chapter 2 (note that a formal charge on an atom does not necessarily denote the partial charge distribution in a bond). Then, put in the given box the label of the hydrogen atom that is most electron-poor. b. A proton transfer reaction can occur from protonated methanol to ammonia. In the box on the left, circle the atom in ammonnia that is most electron-rich. In the box on the right, use curved arrows to show the mechanism of the proton transfer reaction based on the sample proton transfer reaction shown in the textbook. Then, draw the products of the reaction (Lewis structures or line structures accepted). Do not draw the transition state. ! " ! # ! # ! # ! " $ % &'() +,+-).'/01''. 234.'5+/ 6! # '. ! " 789 ! " !"#$ &'()*+ ,((#$- .(,$ /(#+'&0- "*(* 1 2 1 1 1 2 1 1 1 3 1 , 1 , 1 , 1 3 4 5 1 2 1 1 1 1 , 1 , 1 , 1 3 4 5

CHEM 40A Fall 2023 ©2023 Dept. of Chemistry & Biochemistry . Do not copy or distribute without permission. 2. A proton transfer reaction can involve a substance without non-bonding electron pairs as the electron-rich reactant. a. This is 2,3-dimethyl-2-butene. Draw a very minor resonance contributor that involves charge separation. Make sure you show all formal charges and non-bonding electron pairs. Show any curved arrow(s) involved to reach your resonance contributor. b. A proton transfer reaction can occur from hydrochloric acid to 2,3-dimethyl-2-butene. In the box below, put the structure of your answer from (a) next to HCl. Use curved arrows to show the mechanism of the proton transfer reaction based on the sample proton transfer reaction shown in the textbook. Then, draw the products of the reaction (Lewis structures or line structures accepted). Do not draw the transition state. 3. A one-step nucleophilic substitution reaction can occur between the following two reactants. Circle the most electron-poor atom (this atom is in the electrophile) and put a box around the most electron-rich atom (this atom is in the nucleophile). Use a straight arrow to point at the leaving group. 4. Predict the carbon-containing product of each of the following one-step nucleophilic substitution reactions, draw the product in the given box (Lewis structures or line structures accepted). 5. Predict the carbon-containing product of each of the following reactions, draw the product in the given box (Lewis structures or line structures accepted). Show the mechanism of the reaction with appropriate arrows, make sure to include all non-bonding electrons as well. A one-step nucleophilic substitution reaction can occur between the following two reactants. Circle the most electron-poor atom (this atom is in the ! " # # ! " # # #! " #! " ! " # # ! " # # #! " #! " ! " # # ! " # # #! " #! " ! #$ ! " # # ! " # # #! " #! " ! #$ !" # $ I + K OCH 3 Cl + CH 3 CH 2 S Li !"# $ "# % ! "# $

CHEM 40A Fall 2023 ©2023 Dept. of Chemistry & Biochemistry . Do not copy or distribute without permission. electrophile) and put a box around the most electron-rich atom (this atom is in the nucleophile). Use a straight arrow to point at the leaving group. a) b) c) OSO 2 CH 3 KBr acetone Cl CH 3 CH 2 ONa CH 3 CH 2 OH Mechanism Mechanism Mechanism O S O O CH 3 K Br Br O S O O CH 3 K Br O S O O CH 3 K Cl CH 3 CH 3 O Na O Na Cl O Na Cl No reaction Cyclobutane doesn ’ t have leaving group. Also, there is no electron poor carbon to accept nucleophile.

Your preview ends here

Eager to read complete document? Join bartleby learn and gain access to the full version

Access to all documents
Unlimited textbook solutions
24/7 expert homework help

CHEM 40A Fall 2023 ©2023 Dept. of Chemistry & Biochemistry . Do not copy or distribute without permission. d) e) Mechanism Mechanism O S O O C N Na C N O S O O Na C N O S O O Na I NH 2 Na NH 2 Na I NH 2 Na I

CHEM 40A Fall 2023 ©2023 Dept. of Chemistry & Biochemistry . Do not copy or distribute without permission. 6. Shown below is a reaction coordinate diagram for a reaction with a two-step reaction mechanism. a. Label the x-axis and y-axis with the appropriate titles. b. Place the correct labels from the following list in the rest of the given boxes: Label Meaning R Reactant(s) P Product(s) I Intermediate(s) TS 1 Transition state of step 1 TS 2 Transition state of step 2 Δ G ° rxn Standard free energy change of the reaction c. Is the first step or the second step the rate-determining step? Put your answer in the box given below. First step d. Is this reaction exergonic or endergonic ? Put your answer in the box given below. Endergonic